It’s hard to imagine, but there was a time when our favorite stars weren’t known by a lot. There was a time that they were not in the limelight. Do you sometimes wonder what their lives were like before they came into the industry? I don’t know about you, but we love to know about their past, especially if it comes with a good old romance story. If you’re like us, then you might be curious about their love life before. Well, you came to the right place.
We’ll be talking about these stars’ significant others, before – and after – they entered Hollywood. From Beyoncé to Gal Gadot to Vanessa Hudgens, we have the details here. You might be surprised to know who dated who as well as who they are dating now.
Furthermore, we should give these stars some credit for not keeping their love lives private. We all know how hard it is to handle relationships and heartbreaks with the whole world watching. However, these stars have aced the highs and the lows of the dating game mighty fine. Read on to see whose hearts got broken – or they’ve broken – and ultimately, who fixed those broken hearts or entered them.

Ashton Kutcher

Many cute Hollywood couples have made the world fall in love with them right away. Ashton Kutcher and Mila Kunis, on the other hand, are in a league of their own. They met during their teenage years during the filming of the series The 70’s Show. After the show, they became romantically involved with other actors but were gravitated towards each other a decade later. From their onscreen romance as Jackie and Kelso in the hit series to getting married and having two kids, they indeed have one of Hollywood’s most incredible love stories.

Given his fame and investments, Ashton dated a string of beautiful women in Hollywood. Before he got his breakthrough role as Michael Kelso in the mid-’90s, he dated actress Monet Mazur. They were two aspiring actors back then, which could probably be one reason why they broke up after a year. However, his most notable partner before his current wife is probably model January Jones. They dated in the late 1990s; unfortunately, they kept details, such as how they met, private. Their relationship lasted until 2001, which at the time, was Ashton’s longest relationship.

Anna Farris

She’s talented and stunning, and she’s popular, to a degree, that she has become one of the Hollywood sweethearts. Now that Anna Faris is back on the market after her split from fellow actor Chris Pratt, some fans might be curious about who she has dated in her life. Sure, she certainly had a few college flings and high school sweethearts, but her post-fame romance count is minimal.

After co-starring in the 1999 horror film Lovers Lane, Anna met Ben Indra for the first time. They married in June 2004 but split in April 2007, citing irreconcilable differences. She then met Chris and got hitched in 2009. After eight years of marriage, the pair declared their decision to separate legally. Now, she is in a relationship with Michael Barrett, which she tries to keep private. It also appears that Anna may be open to remarrying after all, as she and Michael are now engaged.

Anna Kendrick

It’s uncommon to come across a celebrity that is so well-liked. Well, one of these celebrities is Anna Kendrick, the star of the Pitch Perfect franchise. She’s a natural in romcoms, musicals, dramas, and even vampire teen movies. Despite her degree of fame, she keeps both her lifestyle and her relationship simple.

It’s no wonder that her dating life has been relatively drama-free, given her low-maintenance demeanor. Since becoming popular after 2009’s Up in the Air, she’s been in two long-term relationships and has only been the topic of a few romances. Anna is known to have had a four-year relationship with Edgar White. Currently, she is dating Ben Richardson, whom she met during the filming of Drinking Buddies. Their relationship has been kept private, and they have only been photographed together in public on a few occasions. It’s amazing, given that they have been dating for almost seven years already.

Anne Hathaway

Anne Hathaway became one of Hollywood’s sweethearts after starring in The Devil Wears Prada. Everyone became enamored with the dark-haired beauty, and she has the romances to prove it. Anne is currently happily married to actor Adam Shulman. However, if you think back, her love life was very different.

Years before her marriage, the media was less interested in writing about her love life because she was younger and not yet the big star she would become. According to sources, Anne had long relationships with restaurateur Scott Sartiano, fellow actor Hugh Dancy, and actor Topher Grace. She also had a 10-year romance with an Italian con artist named Raffaello Follieri before marrying her husband. After Raffaello’s departure to Italy, Anne’s degree of fame has been on the rise, and her new appearance in the box office hit Ocean’s 8 was just the cherry on top.

Ariana Grande

Ariana Grande has been a part of the entertainment industry for more than 15 years. She made her Broadway debut in the musical 13 before starring in Nickelodeon’s Victorious. She rose to pop stardom in 2013 with the release of her single The Way. After that, Ariana had a string of hits like Bang Bang and Dangerous Woman before finally scoring her first number-one single with Thank U Next. As Ariana’s music degree grew in popularity, her personal life became a public topic of discussion.

She dated actor Graham Phillips for three years after meeting him on Broadway musical 13 when she was a teenager. She then dated Nathan Sykes and had a long-distance relationship with Australian YouTuber Jai Brooks. Still, her relationships with Big Sean, Mac Miller, and Pete Davidson drew the most attention from the press and fans. Now, we will be hearing wedding bells as she just got engaged to her current beau, Dalton Perez.

Barbra Streisand

Barbra Streisand is known as one of the most famous musicians of all time. Throughout her six-decade career, she has 33 albums that have reached the top ten charts. Topping off her musical investments, Barbra has won several awards for her acting roles on Broadway and the big screen. She has left an indelible mark on the music industry and is a well-known name in popular culture.

Although we admire her enviable elegance and taste for luxury, she had turbulent relationships at some point in her life. Barbra married actor Elliott Gould in 1963 but separated eight years later. She also briefly dated Prime Minister Pierre Trudeau and tennis champ Andre Agassi. A string of relationships with fellow actors transpired before Barbra met and married her now-husband, James Brolin. Two decades have passed, but she remains to be a Woman in Love.

Ben Affleck

Apart from his fame and investments, Ben Affleck has had several high-profile relationships throughout his career. However, not all of them have had happy endings. Cheyenne Rothman was one of the first women to win Ben’s heart. The couple met at a summer camp back in high school and dated for about seven years before separating in 1997. This was the time the actor rose to stardom, credits to his performance in Good Will Hunting. After, Ben was in an A-list relationship with Gwyneth, and the two dated on and off. They even appeared on screen together in Shakespeare in Love and Bounce.

His relationship with Jennifer Garner turned out to be one of his most unforgettable. The former couple had been married for over ten years and were proud parents to three children. Ben moved on, dating Lindsay Shookus and then Shauna Sexton afterward. It didn’t last as well, and in the early part of 2018, he fell in love with Ana de Armas, his Deep Water co-star, whom he met on the thriller film set in late 2019.


Beyoncé is one of the most influential and successful musical artists in the world today, with millions of albums sold and over a dozen Grammy awards to her credit. She has a life that many people would envy outside of music – she is married to mogul Jay-Z, and the couple has an impeccable fortune and investments. Even though Jay-Z has been her boyfriend for most of her relationship, Beyoncé had another boyfriend for several years before marrying him.

Beyoncé’s first boyfriend was named Lyndall Locke, whom she met as a teenager at youth church. They were too young to be dating, but their relationship lasted much longer than you would expect. Part of the reason for Beyoncé and Locke’s breakup was that she spent most of her time on the road with Destiny’s Child. She was then with Jay-Z as she rose through the ranks of the music industry.

Blake Lively

Blake Lively and Ryan Reynolds are undeniably the cutest couples in Hollywood right now. They’re both experienced actors with high net worths and multiple investments, and they have two young daughters to add to the cuteness of their family. They have been together for years now but Blake had to kiss a few frogs before finding her prince. The list isn’t particularly long, with just four significant others, but they were still notable.

Blake dated her Simon Says co-star Kelly Blatz for three years. She had a childhood crush on him and was friends with him as a kid, but it wasn’t until 2004 that he eventually came around. Apart from Kelly, Blake listed two other men with whom she had flings before dating Blatz, but we know little about those relationships’ seriousness. Lively was also known to have dated Penn Badgley, Ryan Gosling, and Leonardo Di Caprio.

Brad Pitt

Although his handsome features and irresistible charm didn’t catch the public’s attention until his role in the 1991 film Thelma & Louise, the Hollywood sensation was already a fixture in the industry dating pool long before then. While fans are well-versed in the specifics of Brad’s marriages to Angelina Jolie and Jennifer Aniston, he got involved with other celebrities in his younger years.

Brad was linked to Sinitta, a British-American singer, whom he dated for two years in 1984. The singer later revealed that the young Brad was sweet and charming when they were together. After a series of brief relationships with co-stars, he got engaged to Jill Schoelen and Gwyneth Paltrow, but both didn’t push through. Although his marriages with Jennifer and Angelina did not end successfully, Brad is regarded as one of Hollywood’s most eligible and richest bachelors, with a long list of flames and investments to prove it.

Britney Spears

While her life is full of fame and investments, her relationships are often under the radar. Britney Spears has been head over heels in love with Iranian model Sam Asghari for the past four years, but her relationships before that are more than a little fascinating. Life has knocked her a few times, but it seems that she’s finally found her soulmate in Sam.

Britney was only an average teen growing up in rural Louisiana before she became a pop music superstar. It was when she met her first boyfriend named Reg Jones. Her first serious relationship was kept private, but her subsequent involvement with Justin Timberlake was far from that. They appeared like a match made in heaven, but when Justin and Britney ended their picture-perfect Hollywood romance in 2002 after four years of dating, things didn’t end on a happy note.

Cameron Diaz

Cameron Diaz was a mainstay in Hollywood in the 1990s, so it’s not shocking that she’s had her fair share of fame and investments. The actress is married to rocker Benji Madden, with whom she married in 2015. Even though their relationship was unexpected, they soon established themselves as one of Hollywood’s most powerful couples. However, Cameron’s love life has been a long and winding road to the happiest place she’s ever been with her husband.

Long before she reached the peak of her career, she had a brief friendship with video producer Carlos De La Torre, whom she met during a commercial shoot. The day after, Carlos called her, and the two hit it off immediately. They lived together for a while before breaking up in 1994. She’s dated other actors, including Matt Dillon and Jared Leto, since her breakthrough role in The Mask, and she’s even dated one of NSYNC members. The actress was also linked to athletes such as a major league baseball player and a surfer.

Camila Cabello

Camila Cabello gained her degree as a Fifth Harmony member, and she has since gone on to become one of the most-sought solo stars in the industry. She is well-known for scorching the charts, but also for her love life. Who is she dating these days? Well, the gossip mill has been working hard, and it seems that her new beau is Shawn Mendes, which is fantastic news for fans who have been rooting for them since their collaboration in 2015.

While she is in her happiest state, the singer got linked to several celebrities over the years. Camila dated Austin Mahone in 2014 when Fifth Harmony was on tour opening for the singer. It’s unclear why they broke up in the end, but Austin had nothing but positive things to say about his ex, so things seem to be okay between them now.

Cara Delevigne

Cara Delevingne has snatched our hearts in the same way Margo did in Paper Towns. We’re not the only individuals who are captivated by those brows; the model-turned-actress has broken the hearts of both men and women since her public debut. However, things may be looking up for Jaden Smith as of February 2021. The pair sparked romantic speculation after pictures of them kissing behind a massive bouquet of roses surfaced. We don’t know what’s going on with these two, so we’ll wait for their blossoming romance.

Cara was romantically related to other big names in the entertainment industry. Her romance with British musician Jake Bugg became known in the winter of 2013. It was a great year for both of their careers as she was gaining traction in the modeling industry – landing hundreds of magazine covers – while Jake was playing at a big US festival, Coachella. Sadly, their hectic lives seemed to be the reason for their split.

Catherine Zeta-Jones

Catherine Zeta-Jones’ marriage to Michael Douglas is indeed her most significant one. While she admitted that her 20-year marriage to Michael had had its ups and downs, she credits their long-lasting marriage to maintaining a close bond. Michael and Catherine got married in 2000 and now share two children. They spent years away from Hollywood while juggling their career and raising their kids. However, what if Catherine and Michael had never met?

After landing a part in the successful ITV drama series The Darling Buds of May, Catherine became a household name. Her fame introduced her to John Leslie, whom she met at a Chesney Hawkes concert in 1991. Sadly, the pair broke up after 18 months, because, allegedly, Catherine wanted to build a family and he didn’t. Two decades have passed, and she chose to put the Leslie situation behind her to focus on her family.

Chris Pratt

Chris Pratt has become one of the most sought-after actors after portraying Star-Lord in the hit movie, The Guardians of the Galaxy. Yes, he is currently engaged to Katherine Schwarzenegger, but before that, the actor had dated several of his co-stars even before he made it big on screen. He dated Emily VanCamp, whom we all know from the TV show, Revenge. The two starred in Everwood where they were cast as siblings. Many found their relationship a bit weird since they can’t get the idea of these two being brother and sister out of their heads. Well, they didn’t have the time to get used to it because the couple separated after a few years.

Chris then courted Anna Farris, whom he met on the set of Take Me Home Tonight. The actress was married to someone else back then, but don’t worry, Chris waited until Anna was divorced to woo her. They tied the knot later on and had one son named Jack Pratt. Unfortunately, after eight years of marriage, they decided to hire lawyers and get separated.

Christina Aguilera

Christina Aguilera stole the hearts of many when she became a superstar at just 19 years old. The singer dazzled everyone with the range of her voice and she became an overnight sensation. With the spotlight on her and the media following her every move, her personal relationships became public, too. There were rumors that Christina and Enrique Iglesias became an item, but they did not confirm it. She was also linked to Fred Durst, too. However, what was confirmed is her relationship with Jorge Santos, which lasted for two years.

There were other men in the hit singer’s life but they did not last long. After she separated from Jordan Bratman, Christina started dating Matthew D. Rutler, who was a production assistant from the movie Burlesque, which the singer starred in. He proposed to her on Valentine’s Day, and now, they have a beautiful daughter together named Summer Rain. The couple has numerous investments, which can be used to raise their family.

Cindy Crawford

Even before Cindy Crawford became one of the most sought-after supermodels across the globe, she was dating her high school sweetheart, Bill Cordes. They were even crowned as Prom King and Queen back then. However, their young love changed when Cindy was discovered by a talent scout and started gaining attention in the fashion industry. Sadly, the two said their goodbyes as she pursued a career in modeling.

Over the years, Cindy dated many A-listers in Hollywood and even married some of them like Pretty Woman actor Richard Gere. She was also linked to John F. Kennedy, Jr. and Val Kilmer, before settling with former model Rande Gerber. They have two children who followed in their parents’ footsteps and are now models themselves. With the couple’s earnings and proper investment planning, their children are probably set for life.

Courtney Cox

After playing the role of Monica in the hit TV series, F.R.I.E.N.D.S, Courtney Cox became an overnight sensation along with the rest of the cast. There is no denying that her performance there was riveting and she had gained numerous accolades because of it. We then saw the actress date other Hollywood actors such as Michael Keaton, who took on the role of Batman. They started dating in 1989 after Courtney casually mentioned to their mutual friend that she liked him especially in Clean and Sober. Unfortunately, their relationship ended after six years.

Courtney went on to pursue her career in Hollywood where she also met several guys, such as David Arquette, with whom she had a relationship. Currently, her partner is Johnny McDaid, who is a singer and actor. The couple got engaged just six months after they started dating. They called it quits after a year and a half, but the good news is – these two are back again. We hope they get married soon, and we would never hear any news about them hiring lawyers and separating in the future.

Demi Moore

Hollywood star, Demi Moore, has had her fair share of relationships during the course of her career. Her first marriage was to rock musician Freddy Moore. The pair started seeing each other back in 1979 even though he was married while Demi was still with Tom Dunston. In an interview, Freddy stated that it was Demi who insisted that he hire lawyers and separate from his wife, which he did. Although their marriage was great at the start, it quickly soured until the couple broke up after five years.

Demi went on to marry Bruce Willis, and their relationship lasted for 12 years. Their separation was amicable and they are still great as exes and co-parents. Many were then stunned when she married That 70s Show actor Ashton Kutcher, who became close to Demi’s ex and children. The latest relationship the actress had was with Sean Friday, who is a drummer by profession.

Drew Barrymore

Drew Barrymore is one of the most popular names in Hollywood since she had been acting since she was a little girl. She made her acting debut in the show Firestarter. By the time she was 14 years old, Drew made a red carpet appearance with her then-boyfriend Corey Feldman, an actor who is best known for his role in the film, The Goonies. Although the two looked good together, their relationship did not last long. Would you believe that Drew got engaged two years after? Unfortunately, that one didn’t push through.

Her first marriage was to Jeremy Thomas, who was an LA bar owner, but it only lasted for 19 days. Another husband that entered the picture was Tom Green, whom she met on the set of Charlie’s Angels. What they had was a whirlwind romance, which eventually ended, too. Her most recent husband was her longtime friend, art consultant Will Kopelman. They got married in 2012, but they separated four years later. At least it was an amicable one, so their assets and investments were probably divided based on an agreement.

Ellen Page

Elliot Page, formerly known as Ellen Page, is one of Hollywood’s promising stars. The Umbrella Academy star has been open about her gender and her transition over the years. However, before she became Elliot, she had some interesting relationships while she was just starting out in Hollywood. There were rumors abound that the then-Ellen was dating Ben Foster in 2006 whom she met on the set of X-Men: The Last Stand. The two neither denied nor confirmed what was going on between them, but they do look great together.

She was also once in a relationship with Mark Rendall and then Emile Hirsch, but her preferences for a partner soon came to light. There were rumors that she dated female stars, and eventually, she opened up about being with artist Samantha Thomas. Unfortunately, their romance lasted for 2 years only. After announcing that she would like to be addressed as Elliot Page, he went on and married Emma Portner, who is a dancer and a choreographer. Unfortunately, they hired lawyers and split up just recently.

Gabrielle Union

Gabrielle Union has been linked to several athletes during the start of her career. She had a relationship with Juan Dixon, who was a professional basketball star. Their romance was brief and Gabrielle went on to date actor and rapper, Ludacris, and then Darren Sharper, who was a former NFL player. Although the two looked great together, they only dated for a year until they split. However, the most notable relationship before her current husband would probably be her first marriage, which is with Chris Howard. They got married in 2001 and then separated four years later.

Gabrielle is currently married to NBA star Dwyane Wade. Their relationship was a bit rocky at the start after Dwayne’s ex-wife filed a suit against the actress. However, Union did not succumb and was able to beat the lawsuit. The couple then got married in a private ceremony, and they now have a child together via surrogate. They have made investments in IVF treatments for them to get pregnant, but they got their child via surrogacy instead.

Gal Gadot

Gal Gadot has certainly caught the attention of Hollywood and its viewers for her portrayal of Wonder Woman. However, she has been in the acting business for some time now. She first started with Kicking Out Shoshana where she met and dated co-star Oshri Cohen. Although the couple did spend some time together, their relationship did not last long. Gal went on to star in various films such as Knight And Day, Fast Five, and Keeping Up With The Joneses.

Although the Israeli beauty has certainly turned heads wherever she goes, so whoever she ends up with will be very lucky. In fact, we have the name of this lucky guy. The actress found the love of her life, Yaron Versano, who is a successful businessman. They are currently married for 12 years and have two children – with another baby on the way. They probably won’t have to consider applying for student loans for their growing brood since their earnings are enough to cover tuition expenses.

George Clooney

George Clooney is one of the most popular men in Hollywood and one of the most sought after, too. He was known for dating several women during the early years of his career. Many may not know this, but he first dated Michelle Pfeiffer’s sister, Dedee, back in the days. He later married Talia Balsam in 1989 but the couple split in 1993. Of course, George was able to get back to the dating scene without any trouble. The E.R. actor was then romantically linked to Elisabetta Canalis as well as Lisa Snowdon, whom he had dated for five years. Before his current wife, George was once with an item with Kelly Preston. He used to consider their relationship “the most important thing” for him, but in the end, they went their separate ways.

Although many thought that the Ocean’s Eleven star would not be tied down after Kelly, he met Amal Alamuddin and he was just smitten with her. They first met at his home in Lake Como, and right then and there, they both knew that they were meant to be together. The couple is already married and has twins to dote on. We hope we would never hear any news that this couple has hired lawyers and is getting separated.

Gigi Hadid

Gigi Hadid has been flourishing in her modeling career, and with all the media attention that she has been getting, her personal life became available to the public. She first dated the Australian pop star, Cody Simpson, from 2013 to 2015. However, their relationship was more on and off than steady dating. They did split eventually but in an amicable manner. Gigi was later linked to Joe Jonas, but this was short-lived as well.

The model was later spotted with singer Zayn Malik and both were not shy about their relationship, which they show on their Instagram. The two separated after seven months of dating but got back together eventually. Currently, they are now engaged. With successful careers and several investments, they probably won’t have any trouble with the wedding expenses or when they start their family. We can’t wait to see what their children would look like!

Gwyneth Paltrow

Gwyneth Paltrow has become quite the Hollywood celebrity thanks to her role as Pepper Potts in the Iron Man and Avengers franchise. The actress had quite a stellar career as well after appearing in films like Se7en, Shakespeare in Love, and A Perfect Murder, just to name a few. However, before she landed in the arms of Brad Falchuk, the actress had dated several men starting with Donovan Leitch Jr. They were dating back in the early ‘90s, and after they split up, she moved on and dated some of the most popular men in Hollywood.

Gwyneth became Brad Pitt’s girlfriend after they met on the set of Se7en. Their relationship was not kept from the public, and Brad even proposed to her as well. Unfortunately, they called off their engagement seven months later. She got married to Coldplay’s Chris Martin but their relationship ended after ten years. Currently, Gwyneth is engaged to Brad, whom she met in Glee. They have kept things under wraps, but they are definitely spending their investment money on this beautiful occasion.

Halle Berry

Halle Berry is a Hollywood icon, who has several films under her name such as Gothika, Swordfish, Monster’s Ball, and Die Another Day. She also had her fair share of relationships with some of the hottest stars in Hollywood, too. She dated Kevin Costner, but her first husband was baseball star David Justice from 1991 until 1997. She later dated Criminal Minds star Shemar Moore but this only lasted a year.

Halle went on to date Billy Bob Thornton and Micheal Ealy. She also had a relationship with Gabriel Aubry for five years and had a daughter with him named Nahla Ariela Aubry. However, the couple split up, and Halle took custody of their daughter. She later married actor Olivier Martinez in 2013 and had a son with him. Unfortunately, the marriage did not last long as they announced their split in 2016. Although Berry may not have that much luck in men, she is good at money management as she maintains her net worth at a good number.

Isla Fisher

Isla Fisher rose to fame in her performance in the film Home & Away. It is also here where she started dating her co-star, Shane Ammann. The couple was an item for a year until they went their separate ways. The Confessions of a Shopaholic star was later spotted with English actor Darren Day and were together from 1998 to 2000. Afterward, the actress focused more on her career instead of finding love.

In 2002, Isla met Borat actor Sacha Baron Cohen at a party that was held in Sydney. From there, the two started dating and later became engaged in 2004. The couple tied the knot in 2010 and are currently doting parents to three children. Although Isla is not as active with her acting career as before, to her credit, she is a great mother to her children, which earned her much respect and love from her partner.

Janet Jackson

Janet Jackson may have risen to fame thanks to her family name, but she is a celebrated singer on her own right. Her musical career began in the ‘70s when she appeared in the variety show The Jacksons. From there, her career just went on to new heights, where she even received the Billboard Icon Award in 2018. Of course, Janet had been in several relationships back then, with James DeBarge being the first one she had married in 1984. Unfortunately, they hired lawyers for their separation after a year.

Janet then got married a second time around which lasted for nine years. Her third marriage was with Wissam Al Mana; they tied the knot in 2012. Although Janet wanted to keep her personal life as private as possible, when rumors broke that she was going out with the Qatari mogul, Wissam Al Mana, everyone wanted to know how it happened. Currently, the couple has separated, and it seems that it wasn’t amicable.

Jennifer Aniston

The 50-year-old actress has had her fair share of relationships during and even before her acting career has bloomed into what it is today. Her first love was the actor, Daniel McDonald. The couple dated back for four years, from 1990 to 1994, before she made her screen debut on the popular and classic television series, Friends. Jennifer also dated Adam Duritz while trying to get over her tragic first love, but the relationship quickly died out. However, her first serious boyfriend was Tate Donovan, whom she dated from 1995 to 1998 and was even briefly engaged towards the end. Jennifer also dated a couple more A-listers throughout her career but no one comes close to her second love – Brad Pitt.

She and Brad met way back in 1998 and was one of Hollywood’s hottest couples. The power couple was married for five years, from 2000 to 2005, but much to everyone’s despair, the pair called it off in 2015. Jennifer was then married to Justin Theroux, but unfortunately, they hired lawyers and finalized their separation in 2017.

Jennifer Garner

After Jennifer appeared as a guest star on Felicity, she and Scott Foley couldn’t help but have a strong connection with each other. They ended up making their relationship official by exchanging vows in October 2000. Jennifer and Scott were married for three years before getting separated, making their split official in March 2004. She then dated Ben Affleck back in 2004, going public with their relationship after appearing together on Daredevil. The pair got married in June 2005 and became proud parents to three wonderful children. That’s why fans were devastated when the couple hired lawyers and officially announced their separation in October 2018, which Ben admittedly said was his ‘biggest mistake.’

Jennifer’s most recent relationship was with John Miller, whom she dated back in 2018. The sparkling romance was short-lived after they parted ways in August 2020, but they still remained on friendly terms.

Jennifer Lawrence

Jennifer first started going out with Nicholas Hoult after meeting on the set of X-Men: First Class in 2010. They dated until 2013, had a brief break, reconciled, and then called it quits for good while filming X-Men: Days of the Future Past in 2014. Shortly after her romance with Nicholas ended, she dated Coldplay’s frontman, Chris Martin, in June 2014. Unfortunately, things didn’t last and rumors of their split surfaced in October 2014, which was only confirmed in August 2015. There were also rumors speculating that she and her co-star from the movie Hunger Games, Liam Hemsworth, were dating and that she also had a relationship with the director Darren Aronofsky, whom she worked with on Mother! The latter seems to be true since there was news that they broke up after a year of dating.

Following her split from Darren, the actress then began dating the art dealer, Cooke Maroney. They are now engaged, which was confirmed back in January 2019. With their successful careers and investments, they can surely afford a grand wedding.

Jennifer Lopez

Jennifer was with her first husband, Ojani Noa, back when the aspiring performer was still a waiter at a Miami restaurant during the late ‘90s. Not much is known about their relationship since they called their lawyers and separated in January 1998, after 11 months of marriage. She then dated fellow music artist Sean John Combs from 1991 to 2001. The pair started seeing each other around the release of Jennifer’s debut album On the 6 and even got arrested together. Their relationship, however, was full of infidelity and was quite turbulent, which eventually led to their breakup.

The musician’s second husband was dancer and choreographer Cris Judd to whom she was married for just 9 months from 2001 and 2002. The pair met on the set of her music video, Love Don’t Cost a Thing, which Cris himself directed. Jennifer also dated a few other artists throughout her career, even got married and engaged to some. However, right now, Jennifer is currently single after her breakup with her ex-fiance, Alex Rodriguez.

Jessica Biel

Believe it or not, Jessica Biel has dated a few bigshot Hollywood stars before settling down with Justin Timberlake. Back in her early career, she and Adam LaVorgna, who is best known for his role on Brooklyn Bridge, Milk Honey, and The Beautician and the Beast, started dating back in 1998 after meeting on the set of I’ll Be Home for Christmas. They dated for almost three years before splitting up in 2001.

Shortly after her relationship with Adam, Jessica started dating Chris Evans in 2001. They even co-starred together in the 2004 movie, Cellular, where their chemistry was, to a degree, perfect. Unfortunately, the couple called it quits in 2006. She was then rumored to be dating Derek Jeter, but the relationship didn’t last long as it was more of a fling. Jessica then started dating Justin Timberlake in 2007 after meeting at one of his parties. They talked, got together well, took a break, and then got married in 2012. They had their first son, Silas, in 2015.

John Mayer

In the early 2000s, John Mayer dated his fellow chart-climber, Vanessa Carlton. However, they called it quits in 2002, and shortly after, he was linked to Jennifer Love Hewitt. Unfortunately, they didn’t last long together. He then began seeing Jessica Simpson in 2006, but when he referred to her as “sexual napalm” in a 2010 interview, it was the final straw that ended their on-off relationship.

Some of his other flings were Jennifer Aniston, Cameron Diaz, Rashida Jones, Scheana Marie, and Taylor Swift, who he dated back in 2009 when she was still 19 years old and John was 32. He was also briefly linked to Kim Kardashian but it was just a baseless rumor. His only long-term girlfriend was Katy Perry, whom he dated from 2012 to 2016. They had a collaborative song together titled, Who You Love. John even dedicated his lovesick song, Still Feel like Your Man to Katy, saying that this was his ‘only’ relationship. Well, it was a good thing he never married any of these girls, otherwise, he would have spent a ton on lawyer fees.

Julia Roberts

During her early career days, when Julia Robert starred in 1998’s Satisfaction, 1989’s Steel Magnolias, and many others, she dated Dylan McDermott, Kiefer Sutherland, and Jason Patric. However, her first relationship was with Liam Neeson, dating the star after appearing together in Satisfaction. They were an item for a year before splitting in 1988. She then took a shot at marriage with her first husband Lyle Lovett in 1993. Sadly, their relationship only lasted less than two years, calling it quits in 1995. Julia then met Matthew Perry. The two were linked from 1995 to 1996, and their relationship was rumored to have started after she earned TV credits as a guest star in an episode of Friends.

However, one of Julia’s longest relationships was with her fellow Miss Congeniality actor Benjamin Bratt. They dated for almost four years before deciding to call it off in June 2001. Since then Julia has been happily married to Danny Moder, tying the knot in July 2002. The two have been married for 18 years now and are proud parents to their son, Henry.

Justin Timberlake

Justin struck up his first high-profile yet brief romance with Fergie between 1996 and 1997 -she was then part of the girl group Wild Orchid and going by her birth name, Stacy Ferguson. The couple didn’t come without any controversies though as they were ridiculed by the media. They drew controversy because of their age gap as Fergie was 23 years old and Justin was 16. This relationship was before his most infamous one yet, which was with Britney Spears.

There’s no doubt that he’s in a much happier place right now. Justin and Jessica Biel have been married for a whopping 13 years and are still going strong with their growing family. They’ve never been close to hiring lawyers, and seem to be very happy, as seen in the cute videos they post on their social media. They are currently expecting a child this year and we’ll be sending them our good wishes.

Kaley Cuoco

Kaley Cuoco and Thad Luckinbill dated back in 2002 when they starred in the film 8 Simple Rules. Thad is best known for his longtime role on The Young and the Restless. The couple was quite lowkey and didn’t really show themselves being affectionate in public together. From the looks of it, their relationship felt more like a passing moment than an actual one. They broke up in July 2004 and neither has explicitly talked about their relationship since then. We are glad to see that they moved on and are now happy with different people.

The Big Bang Theory star is married to Karl Cook, who is her second husband. Her first husband is tennis player Ryan Sweeting, and in 2016, they hired lawyers and decided to get separated. Kaley mentioned that she learned a lot about marriage from her first one, which is how she knows she’s on a firmer footing with Karl.

Kate Winslet

Kate Winslet got her heart broken before the age of 21, and she had the liberty to deal with a high degree of emotional pain in private. Stephen Tredre, Kate’s first love, would be the man in the picture. They met in London, England, when they were both ambitious actors – she was 15 years old and he was 28. They started dating in July 1991 but split up four years later in August 1995. Despite their split, the two remained close and maintained their friendship.

In 2011, Kate met her third husband, Richard Branson’s nephew Ned RocknRoll or formally known as Edward Smith, while staying on Sir Richard’s Necker Island. Their fateful meeting occurred during the typhoon that decimated Necker Island in 2011, and when the mansion where Kate and her children were staying went up in flames, Ned became the hero who led them to security. Before Ned proposed, the couple had been dating for nearly a year, beginning in September 2011. They got engaged in August 2012 and married on December 5 of that same year.

Katherine Heigl

Katherine Heigl and Joey Lawrence had an exhilarating romance for three months in 1994. Like every other celebrity teenage romance, this was all just pure innocence. We’re glad that they kept their investment in this relationship to a minimum as they get to explore much more experiences with different people. The teen couple were just experiencing young love at its finest and finding their way to better things back then. It’s kind of sweet looking back at their interviews because of how much they gush about each other.

Katherine has a reputation for being complicated to handle, but we doubt her husband, Josh Kelley, feels the same way. They got married in 2007 and are still together today. According to sources, Katherine first met Josh in 2005 when she appeared in his music video for Only You. After that, they wanted to grow their family and decided to adopt. They adopted Naleigh from South Korea and later Adalaide Marie Hope from the same country. After that, the couple decided to have a biological child. They were overjoyed to welcome Joshua Bishop into their family in 2017.

Katy Perry

One of Katy’s earlier relationships was with a guitarist named Justin York. He has a much recognizable brother named Taylor York, who is a member of the band Paramore. She started dating Justin even before she got a major record deal. She was still in her Christian era at that time, making gospel and soft mellow pop songs. However, the person who inspired a lot of her songs is former partner Johnny Lewis. They dated for a year, but it seems that things didn’t work out in the end.These relationships weren’t really major news since Katy was not as famous as she is now back then.

Now, everything about her is important. For one, she and her Pirates of the Caribbean husband, Orlando Bloom, revealed the arrival of their first child, Daisy Dove Bloom, last year. She joined the family just over a year after the couple announced their engagement in February of 2019. While the couple’s relationship has been notoriously tumultuous at times, it appears the two are now living their best lives together, alongside their daughter, who is eight months old. Despite the fact that they had their two-year engagement anniversary on Valentine’s Day, it appears that they were more concerned, to a degree, about their daughter than the ceremony.

Kelly Ripa

Kelly Ripa and Vincent Young were seen together as an official couple back at the 11th Annual Soap Opera Digest Award in Beverly Hills. His most known work was in Beverly Hills 90210. As many of the first relationships stated in this list, the once couple never really took the degree of their relationship seriously. They only had a brief relationship, spanning for a few months only. We are glad that they at least tried dating, even if it ended with them wanting to spend eternity with different people.

Kelly Ripa first met Mark in 1995, when she landed a role on ABC’s All My Children. She had been playing Hayley Vaughan on the soap for five years at this point. They got married in 1996, and their first child was born a year later. On June 2, 1997, a year into their marriage, Kelly gave birth to Michael. Today, the couple has three children: the aforementioned Michael Joseph Consuelos, their daughter Lola Consuelos, and their youngest child Joaquin Consuelos.

Kristen Bell

Kristen Bell and Matthew Morrison are one of the most unexpected couples who have gotten together. They dated way back in college and revealed that they even gave cute nicknames to each other. It helped that they have common interests such as a passion for acting and also a love for musicals. We can’t help but be envious of their degree of maturity as they remained close throughout the years and seem to be on good terms with each other.

Kristen then met Dax Shepard, and now, they have a marriage that is envied by a lot of couples. They’ve been together for 11 years, married for seven—a rarity in Hollywood—and aren’t afraid to be open about their feelings. Dax proposed to Kristen in 2009, but the couple notably waited until same-sex marriage was legalized in California before marrying. On October 17, 2013, they married at The Beverly Hills Courthouse. They have two daughters, Lincoln Bell Shepard and Delta Bell Shepard, who were born in 2013 and 2014, respectively.

Kristen Stewart

Angarano and Stewart met on the set of the indie drama “Speak” in 2005 when they were teenagers and instantly fell in love. Their picturesque relationship was put to the test when Stewart was cast as Bella Swan in Twilight opposite the equally brooding heartthrob Robert Pattinson, whom she hand-picked as her leading man. There were many signs that the two co-stars were getting into each other so Angarano felt the need to break up with Kristen before the situation escalated to some degree.

Kristen Stewart and Dylan Meyer’s relationship is stronger than ever as they approach their one-year anniversary. Meyer and Stewart were first romantically linked last summer, but they actually met in a movie set six years before. They later reunited at a mutual friend’s birthday party. The actress, who will play Princess Diana in an upcoming film and is currently starring in Hulu’s The Happiest Season, revealed that she is ready to propose and we hope to see them have a happy ending.

Leonardo DiCaprio

Aside from his acting career, award-winning actor Leonardo DiCaprio is well-known for his numerous relationships over the years, especially since he chooses partners who are 25 years old or younger. One such partner was model Nina Agdal. They were first spotted together in May 2016 at a nightclub in New York City.  A few months later, it was reported that their relationship was becoming serious. However, in May 2017, they both announced that they called it quits. It seemed that DiCaprio could not make an investment towards settling down for good.

Currently, DiCaprio is in a relationship with model and actress Camila Morrone. They were rumored to be dating in December of 2017. In March 2018, a very rare display of affection between them was captured on camera during their time in Los Angeles. While the age gap of 23 years has made a lot of noise, it seems the couple is happy. They celebrated the New Year together in 2020.

Lisa Kudrow is globally known for her role as Phoebe Buffay in the sitcom Friends. Kudrow has been romantically involved with two people; her first one being the comedian and late-night host Conan O’Brien. In an interview with More magazine in 2011, Kudrow revealed that she once dated O’Brien during the early 1990s. At the time, Kudrow and O’Brien were members of the improv group Unexpected Company. However, their relationship did not last for long, as Kudrow admitted that they were not meant for each other. Regardless, Kudrow and O’Brien remained friends and have been supportive of one another, and Kudrow credits O’Brien for further pushing her towards acting.

Currently, Kudrow is married to French advertising executive Michel Stern. Both met in the late 1980s but only got married in 1995. They have a son, Julian, who was born in 1998. Julian is currently in college while the couple is living happily after 25 years of marriage.

Leighton Meester

Leighton Meester was quite well-known for her modeling, acting, and singing career. She is best known for her portrayal of socialite Blair Waldorf in Gossip Girl. Just as she was building a fanbase for herself, Meester became romantically involved with co-star Sebastian Stan in 2007. Stan was a recurring cast member of Gossip Girl at the time. In 2008, after many rumors, they publicized their relationship. In 2009, they were photographed kissing during a basketball game. However, they called it quits by 2010.

Currently, Meester is married to actor Adam Brody. They first met during the taping of The Oranges. They became engaged in 2013 and tied the knot in February 2014. Together, they have two children, a daughter, and a son. Meester and Brody are quite mum about discussing their children but are quite committed to raising them. Aside from her career, Meester has volunteered and made investments in various organizations such as Safe Horizon, Feeding America, and Many Hopes.

Maggie Gyllenhaal

For many, Maggie Gyllenhaal is best known for her appearances in films and TV series such as Donnie Darko, Secretary, The Dark Knight, and The Honourable Woman. Like her younger brother Jake, Maggie has garnered multiple accolades over the years, including two Golden Globes. Gyllenhaal has been together with actor Peter Sarsgaard for nearly two decades. Sarsgaard and Gyllenhaal became romantically involved in 2002, through Jake, who is also Sarsgaard’s friend. Both Gyllenhaal and Sarsgaard are heavily active in theater. They became engaged in April 2006 and on May 2, 2009, tied the knot in a ceremony in Italy.

Since then, they have had two daughters, Ramona and Gloria Ray. In the year of their engagement, Gyllenhaal and Sarsgaard bought a 3,600 square foot townhouse for $1.91 million. The renovations done on the house led to it being featured in Architectural Digest. In 2019, they put up the townhouse for sale for nearly $4.6 million, a return of $2.7 million in investment. The couple has since purchased a new home. It seems like the couple’s relationship would last much longer.

Margot Robbie

Margot Robbie is an Australian actress currently known for her portrayal of Harley Quinn in the DC Extended Universe. She also appeared in numerous films such as The Wolf of Wall Street, Once Upon a Time In Hollywood, and I, Tonya. She has been romantically involved twice, with her first being Henry Aitken, an art director. Robbie met Aitken during the production of Z for Zachariah in New Zealand. However, it seemed that the relationship did not last as they called it quits in April of 2014.

Robbie has been married to Tom Ackerley since 2016. They first met in 2013 but only became romantically involved in 2014. They tied the knot in December 2016 in a private ceremony in Australia. Today, they live together in Los Angeles. As a couple, Robbie and Ackerley made an investment in a production company, LuckyChap Entertainment. The company has produced films such as Birds of Prey, Promising Young Woman, and I, Tonya.

Matt Damon

Matt Damon is a heavyweight in Hollywood. He is well-known for his performances in various films such as Good Will Hunting, Saving Private Ryan, The Martian, and the Bourne trilogy. After the production of Good Will Hunting in 1997, Damon became romantically involved with his co-star Minnie Driver. However, in 1998, they parted ways when Damon announced publicly on The Oprah Winfrey Show that he was single, which caused a media sensation and shocked Driver.

Since their parting, Damon vowed to only date civilians, which he did with bartender Luciana Barroso. They first met at a nightclub in Miami in 2003. Immediately, Damon saw her as his future wife. They became engaged in 2005 and tied the knot in secret in that same year. They share four daughters. The couple keeps their family life private. Currently, Damon and his family live in a $16.5 million penthouse in New York City, which was a massive investment for the actor.

Matthew Perry

A lot of people know Matthew Perry for his role as Chandler Bing on the sitcom Friends. He also appeared in numerous works such as Fallout: New Vegas, 17 Again, and Fools Rush In. He was once in a relationship with actress Lizzy Caplan, who became known for her appearance on Freaks and Geeks and Mean Girls. Perry and Caplan first met in 2006 and dated shortly thereafter. While their age gap of nearly 13 years was an eye-opener to some, they managed to keep their relationship under the wraps. However, they called it quits in 2012.

Today, Perry is in a relationship with Molly Hurwitz. Hurwitz is a literary manager who met Perry back in 2018 and made it official in 2019. While they briefly called it quits in mid-2020, they reunited, and shortly, Perry proposed to Hurwitz in November of that same year. Recently, Perry made some investments towards Friends merchandise, which was sold for charity.

Meryl Streep

Meryl Streep is among the most celebrated actresses in Hollywood, with memorable films such as The Iron Lady, Kramer vs. Kramer, The Devil Wears Prada, and Sophie’s Choice. Throughout her life, Streep was romantically involved with only two people; her first being actor John Cazale. Streep and Cazale became romantically involved during the production of the film Measure for Measure. They performed together in the 1978 film The Deer Hunter and unfortunately, it was Cazale’s last film role. Cazale passed away in 1978 with Streep by his side. His passing had a heavy impact on Streep’s life.

Six months after Cazale’s passing, Streep married sculptor Don Gummer in September of 1978. Together, they have four children. All became successful in their careers in modeling, music, and acting. Throughout the years, Streep and her family have bought numerous investment properties in both the West Coast and the East Coast. Recently, her penthouse in New York was sold for $15.8 million.

Mila Kunis

Mila Kunis is an accomplished actress with numerous credits to her name, including Black Swan, Family Guy, Forgetting Sarah Marshall, and Ted. Kunis is also known for her two high-profile relationships; one with Macaulay Culkin and another with Ashton Kutcher. Her first with Culkin lasted from 2002 to 2011.  Both child actors in the past, they became partners in 2002 — they started with a long-distance relationship that became quite serious. However, they called it quits in 2011 and have remained friends since.

Kunis and Kutcher already had a history together, albeit a professional one. They co-starred in That 70’s Show, which ran from 1998 until 2005. They reunited in 2012 and immediately started dating. In February 2014, they announced their engagement, and in that same year, Kunis gave birth to their daughter, Wyatt. They tied the knot in 2015 and a year later, they had another son, Dmitri. The family currently lives in a $14 million Beverly Hills home, which is a cozy investment for their children.

Michelle Pfeiffer

A superstar during the 1970s and 1980s, actress Michelle Pfeiffer was always in the spotlight. However, this stands in stark contrast with her personal life, which she keeps private. What is known is that Pfeiffer was married twice, to Peter Horton and David E. Kelley. Pfeiffer has worked with Horton in numerous films already. Eventually, they grew close and tied the knot in 1981.  However, they called it quits in 1988.

Pfeiffer first met Kelley on a blind date in 1992 and shortly tied the knot in 1993. Since then, the couple has had two children, daughter Claudia and son John. While they have been together for 28 years, they are adamant that they will not work on each other’s projects, which they attributed to their long marriage. Today, the family lives in their $22.3 million home in the Pacific Palisades. They had former real estate homes as investments in the same area and in Woodside, California but some were sold years ago.

Nicole Richie

Nicole Richie is a TV personality and socialite who became well-known for starring in the reality series The Simple Life. The daughter of singer Lionel Richie, Nicole’s personal life has been extensively followed, including her relationships. She became romantically involved with disc jockey Adam Goldstein, known as DJ AM, in 2004. They became engaged a year later. However, that engagement was short-lived, as the wedding was called off in 2005.  They eventually made amends and remained friends.

Richie first met rock star Joel Madden in 2006. Madden is known as the frontman for the pop-punk band Good Charlotte. They dated shortly and after two years, Richie gave birth to two of their children, Harlow and Sparrow. They made their relationship official by tying the knot in 2010. Since then, the couple and their children have been living happily. While Madden is focusing on his band, Richie has been focusing on fashion, with many investments towards her clothing and perfume line over the years.

Nicole Kidman

Aside from being an accomplished actress, Nicole Kidman is also known for her two high-profile marriages — one with Tom Cruise and one with Keith Urban. Her relationship with Cruise started during the filming of their movie Days of Thunder in 1989. A year later, they tied the knot. During their marriage, they adopted two children, Isabella and Connor. They also appeared together in the films Far and Away and Eyes Wide Shut. However, Cruise called it quits in 2001 when he filed for separation in court. Their lawyers eventually agreed on joint custody of their children.

Kidman’s next marriage was with country singer Keith Urban. Both met in 2005 during a gala and dated afterward. They tied the knot on June 25, 2006, in Australia. They have two children together, Sunday, born in 2008, and Faith, born in 2010. Kidman and her family live together and have homes in Sydney, Los Angeles, Nashville, and New York.

Oprah Winfrey

Known as the Queen of All Media, Oprah Winfrey has captivated audiences for decades and isn’t shy about sharing her thoughts and feelings. Throughout her life, she had been romantically involved multiple times. Among them were John Tesh and her current partner, Stedman Graham. Her relationship with Tesh started in the 1970s and they lived together in Nashville. However, Tesh parted ways with Oprah shortly afterward due to societal pressures at the time.

Oprah’s current relationship with Graham started in 1986 when they both met at a charity drive. They became romantically involved shortly thereafter. Six years later, in 1992, they announced their engagement in People Magazine. However, their marriage never came. Regardless, they remained together for the past 35 years. They keep their relationship as private as possible. Oprah has been active in philanthropy and has made investments through her company, Harpo Productions, which owns The Oprah Winfrey Network, and her husband fully supported her over the years.

Orlando Bloom

Actor Orlando Bloom has been a heartthrob since the 1990s. His famous roles in films include The Lord of The Rings, Pirates of the Caribbean, and Troy. His love life has also been followed, including his high-profile relationships with supermodel Miranda Kerr and pop superstar Katy Perry. Bloom began his relationship with Kerr back in 2007. It eventually blossomed into an engagement by 2010 and a month later, they tied the knot. Together, they have a son, Flynn, born in 2011. They parted ways in 2013 but remained committed to co-parenting.

Bloom met Perry back in January 2016 at the Golden Globes. They became officially involved by May of that year. While they parted ways in 2017, they got back together the next year and announced their engagement on Valentine’s Day of 2019. Together, they have a daughter, Daisy, who was born in August, 2020. The couple has two homes, one in Beverly Hills and another in Montecito, which are multi-million-dollar investments for the family.

P. Diddy

P. Diddy, whose real name is Sean Combs, once dated fellow artist Jennifer Lopez. The rapper and record producer, who made his debut album skyrocket into Billboard’s Hot 100, was in a relationship with the Dance Again hitmaker from 1999 up to 2001. Their romance started during the filming of Lopez’s debut album, making them a power couple in red-carpet events. However, things didn’t turn the way they wanted. Allegations of a third party clouded their split. Lopez once shaded their relationship, saying that she cannot attain the family life she always wanted.

As P Diddy dealt with the split, he went on to secure a more financially stable life. The rapper not only became a famous personality but was also able to make wise money management decisions. He allotted money towards expanding his wealth, from opening a clothing line, founding a television company, and starting a vodka company. The millionaire rapper is now in a relationship with model Tina Louise. The Australian runway star was reportedly building a romance with the rapper in 2020 after they were seen cozying up in Malibu.

Pamela Anderson

Pamela Anderson is one of the best-known stars whose fame is not only because of her career but also because of her long list of high-profile relationships — she’s had many since she rose to fame in the 1990s.

One of her earlier romances was with the famous poker player Rick Salomon. In October 2007, Anderson and Salomon married in Las Vegas. However, the couple’s union did not last long. They consulted their lawyers for a legal separation three months after. In early 2008, they officially ended their relationship. They got back again in 2013 for a second shot at romance. However, it seemed like the two were really not for each other as they separated in 2015 for the second time.

Anderson had a series of relationships afterward before she finally married again. The 53-year-old star has found new love with bodyguard and bodybuilder, Dan Hayhurst. Anderson and fellow Canadian Hayhurst wedded in December 2020 in an intimate ceremony in Vancouver Island.

Penélope Cruz

Penelope Cruz is an A-list actress in Hollywood who has captured many hearts with her beauty, charm, and acting prowess. Starting her career at the age of 15, Cruz made a name for herself as a well-loved leading lady in movies such as The Pirates of the Caribbean and Volver. While she enjoys the fame, Cruz has also fallen in love with a number of Hollywood actors. She was once in a relationship with rom-com actor Matthew McConaughey. They started seeing each other in 2005 on the set of the action-comedy movie, Sahara, which was shot in Morocco. However, their romance did not end in marriage. In 2006, the two confirmed their split.

McConaughey married Camila Alves in 2012 while Cruz moved on with fellow Spanish actor Javier Bardem. Cruz and Bardem married in 2010. The two first met each other in 1992, before Cruz met McConaughey. They even worked with each other in the Pablo Escobar-inspired movie Loving Pablo in 2017. They are considered one of cinema’s power couples and they have a joint net worth of $95 million. They certainly have the wealth to buy investments on the side.

Rachael Ray

Rachael Ray is a multi-talented Hollywood personality. She is not only a TV presenter and host, but she is also a celebrity cook, author, and businesswoman. She hosts the Food Network series 30 Minute Meals and is working her way to building a business empire from her career. She has a net worth of $80 million, making her one of the richest celebrity cooks in the world who no longer worries about cash loans or debts.

Throughout her successful career, Ray entered into a series of relationships. She was once in a relationship with Dan Di Nicola. Despite speculation that Ray intended to tie the knot with him, the two announced their separation. Their romance lasted from 1996 to 1999. Ray finally found the right recipe for love when she married actor John Cusimano in 2003. Ray and Cusimano have been married for 15 years.

Rachel Zoe

For someone like Rachel Zoe, finding love should have been an easy feat. She is a successful personality, a fashion designer, and a businesswoman who has been in the industry for twenty years. She also gained international fame when she starred in Bravo’s reality TV series The Rachel Zoe Project.

One of Zoe’s high-profile relationships was with fellow fashion stylist Brad Goreski. However, they cut ended their relationship after a fight over a project that they were working on, and Zoe stated that she was used. They went on to reveal each other’s dirty linens in the media. Zoe eventually married Rodger Berman in 1996 and is blessed with two children. Currently, Zoe is making more money as a book author and an entrepreneur. Zoe is also set to work with various luxury brands for a styling project, which will surely add to her growing investment money.

Rashida Jones

Rashida Jones received her biggest break in Hollywood when she was welcomed in the cast of the hit comedy series The Office. She played Karen, who has smitten with lead star John Krasinski’s character, Jim. They became on-screen partners but little did people know that they were an item already even before Jones entered the show. They entered a higher degree of friendship and were each other’s “cheerleaders” but the romance was over when Jones joined the show. Despite having a history, they remained good friends and went on with their respective careers and future relationships. Krasinski is now married to A Quiet Place actress Emily Blunt.

In 2018, Jones announced that she was officially dating fellow Jewish and Vampire Weekend singer Ezra Koenig for almost two years already. Aside from the confirmation of their romance, the two also revealed that they already have a baby. The two’s lowkey romance may have contributed to their relationship which remains strong until now.


Rihanna is one of the most popular pop singers in modern times. One of Rihanna’s notorious relationships was with Chris Brown. In 2009, the Rude Boy hitmaker and the Forever singer were involved in an altercation, with Rihanna accusing Brown of assault. Rihanna was able to consult her attorney after the ordeal, and Brown faced the charges and huge media attention.

Rihanna was able to move on from the relationship. She began dating celebrities and fellow musicians again, including Leonardo DiCaprio, MLB star Matt Kemp, and Drake. The Umbrella singer recently dated Saudi billionaire Hassan Jameel. The business magnate and the singer have appeared together in many outings flaunting their romance. Jameel was able to keep up with the hectic schedule of Rihanna even when he had to deal with his own business and investments. However, the two broke up in 2020, and Rihanna moved on with rapper A$AP Rocky.

Ryan Gosling

Ryan Gosling is one of the actors people swoon over, including fellow celebrities. That is why it does not come as a surprise that Gosling has a long dating history. The actor was once in a relationship with Mean Girls star Rachel McAdams. The two started their romance soon after they worked together for the 2004 hit movie The Notebook. They dated from 2005 to 2007 and have amassed many Hollywood fans.

However, it seemed like their love story was only short-lived. As their career skyrocketed, their romance was sacrificed in the process. Gosling is now happily in a relationship with model and actress Eva Mendes since 2011. They met at the set of The Place Beyond the Pines and since then, they became inseparable. They worked together again as a couple in the 2012 movie Drunk History Christmas. Although they have been together for almost a decade and have reached a degree of financial stability where they can start a family, marriage is not among their plans yet.

Ryan Reynolds

Before Ryan Reynolds become the doting father and loving husband of Blake Lively, he was once engaged to the Ironic hitmaker Alanis Morrissette. The singer and the actor had a relationship for five years after meeting in 2002. This was the time when Reynolds was still building his career in Hollywood. Reynolds popped the question to the singer and enjoyed a three-year engagement before calling off the wedding plans. He then moved on with Scarlett Johansson and married her. However, it did not also pan out well, resulting in another break-up.

Despite a series of failed relationships, Reynolds is now happily married to actress Blake Lively while savoring a certain degree of fame. They married in 2012 and are blessed with three kids. Reynolds is known to always swoon over his wife, admitting that he has fallen in love with her more since the birth of their firstborn. The Deadpool actor and the Gossip Girl actress maintain their reputation as one of the most-loved Hollywood couples today.

Sandra Bullock

America’s sweetheart Sandra Bullock was once head-over-heels for ex-husband Jesse James. They married in 2005 and have appeared in plenty of red-carpet events as a loved-up couple. Bullock also gave credit to her former spouse for standing beside her despite her high-flying career. However, many were shocked by the news that the Miss Congeniality star was seeking legal separation following multiple third-party allegations in 2010. James admitted in a recent interview that he indeed got involved with other women during his marriage.

In 2015, Bullock found love with photographer Bryan Randall. It all started when Randall was hired to take photos of the actress’s son’s birthday party. Soon after, Randall and Bullock became best friends and lovers until today. The couple has been together for several years, marriage may be in the offing for the two. We hope that this time, it lasts for good.

Sarah Jessica Parker

Before Sarah Jessica Parker met her current husband Matthew Broderick, she has been on a series of romances inside the entertainment industry. One of the ex-boyfriends of the Sex and the City actress was Ironman star Robert Downey, Jr. They met when they were both 18-years-old on the set of the 1984 drama Firstborn. A few weeks after the meeting, the young stars moved in together in Los Angeles. Despite being together for close to eight years, the two parted ways. RDJ admitted that while he loved Parker, he was not fit for her, citing his unhealthy lifestyle.

While Parker moved on and became a superstar following her Carrie Bradshaw portrayal in the hit HBO series, Downey, Jr. also made himself a multi-million star without money loans or any debts in the banks. He also eventually became one of the highest-paid actors of all time. Parker married Broderick in 1991 and has been with him for the past 20 years. The actress and the Ferris Bueller’s Day Off star welcomed their three kids in the course of their two-decade union.

Sarah Michelle Geller

Aside from the fact that Sarah Michelle Geller’s popularity was gained after her starring role in Buffy the Vampire Slayer, the former teen star also caught media attention for her previous relationships. Jerry O’Connell was her boyfriend shortly after she landed the Buffy role — she shared a short-lived romance with him. It was in 1998 when the two started seeing each other. However, Geller moved on from the Stand by Me actor to another romance with co-star David Boreanaz.

Geller has truly gone past flings and short-lived romances and is now having a steady married life with Wing Commander star Freddie Prinze, Jr. Today, Prinze, Jr., and Geller are not only blessed with two kids, Charlotte and Rocky, they also maintain an impressive list of assets as husband and wife. They have put a lot of investment money into real estate, including a mansion in Bel-Air and an estate in Los Angeles.

Scarlet Johansson

Scarlett Johansson has been into a myriad of relationships in Hollywood before ending up with her current husband Colin Jost. One of her high-profile romances was with Ryan Reynolds. She has been married to Deadpool actor for a time. She married Reynolds in 2008 after briefly dating him for a year. It is a fact that Reynolds was engaged with Ironic hitmaker Alanis Morrissette for three years but ended up marrying the Black Widow actress instead. However, the two ended their union three years after and consulted their attorney to get a legal separation. There was speculation that both were not ready for a relationship following their previous heartaches.

The once photogenic power couple is now happily married to their respective spouses. Reynolds is married to Gossip Girl Blake Lively while Johansson has tied the knot with comedian and Saturday Night Live writer, Colin Jost. Instead of having a lavish wedding, which Johansson can fund using her growing fortune, the two decided to keep it lowkey. They married in 2019 in an intimate ceremony after three years of dating.

Serena Williams

Serena Williams’ success goes beyond the tennis court. She is the world’s number 1 female tennis player and the highest-paid athlete who no longer thinks of credit card bills or debts. Aside from that, Williams is happy and content with her married life after having tied the knot with internet entrepreneur Alexis Ohanian. Before her union with the Reddit founder, Williams was dating musician and actor Common. They had an on-again and off-again relationship for a couple of years until they split in 2010. Common was supportive of Williams even after their relationship, even gushing over the athlete’s success on the tennis court.

Since then, Williams began dating the investor and has formed a family with him. Williams and Ohanian welcomed their daughter Alexis in 2017. Williams was able to juggle her motherhood duties with tennis and her budding career as an actress. She appeared in box-office movies such as Suicide Squad and The Tale.

Taylor Swift

Taylor Swift is not only known as an international pop superstar whose albums and hit songs have reached the top of the charts, but she is also known to have a long dating history since she started her singing career. In fact, Swift gets inspiration from her relationships and turns these experiences into hit songs. The songs We Belong Together, Love Story, and Dear John are examples of this.

One of Swift’s past romances was with Joe Jonas, whom she dated for a couple of months in 2008. There was speculation that Swift’s song, Mr. Perfectly Fine, was a song inspired by her brief relationship with the Jonas Brothers member.  Right now, Swift is in a long-term relationship with English actor Joe Alwyn. The actor, who appeared in Billy Lynn’s Long Halftime Walk movie, has been with the Miss Americana hitmaker for four years. Dubbed as the longest relationship of the pop superstar, Alwyn can take credit for inspiring Swift’s hit song, London Boy.

Tyra Banks

Tyra Lynne Banks, or better known as simply Tyra Banks, is now one of the most prominent names in Hollywood. She started as a model and now is also an actress, producer, writer, and businesswoman. With all the things that she has achieved, it’s not surprising that she eventually became a big name.

Even before she became a big hit as a Victoria’s Secret model, many have already acknowledged the star’s charm. One of those people was John Singleton, whom Banks dated during the early years of her career. Right now, the model is now dating entrepreneur Louis Bélanger-Martin. The businessman has held several high positions, making him quite experienced in his field. While the two have a hectic schedule, it seems they still find time for each other. We need to give credit to the men who know how to make time for their ladies!


Who doesn’t know Usher? The star has practically stepped into almost every part of the industry. He is a singer, songwriter, dancer, actor, producer, and businessman! Talk about talent. Aside from that, the singer is also a known lover. He has formed several connections and relationships in the industry –including romantic ones, of course! One of his earliest relationships was with Tameka Foster, his former personal stylist. They were together for around four years. Some things just don’t work out, and the two later on separated.

Right now the actor is with music executive Jennifer Goicoechea. The couple is actually expecting their first child together! This baby is going to have two big names in the music industry as parents. I think we can all agree that this baby boy (or girl!) won’t be needing any student loans any time soon.

Vanessa Hudgens

Have you seen High School Musical? I have! Around two dozen times, and I hope I’m not the only one. Anyway. Even if you have seen the movie just once, you probably know our beloved leads, Gabriela Montez and Troy Bolton. Vanessa Hudgens and Zac Efron took credit for playing the roles. At the time, they were also dating. The couple’s story didn’t exactly end how their character’s romance did. Hudgens and Efron eventually separated and went their own ways.

However, it was the end of a relationship, not the end of their own independent stories. They continued with their life and found out how bright their future was. Right now, Hudgens looks like she’s really happy with her current partner, Cole Tucker. The actress has gotten her heart broken a few times in the past, and we’re just glad someone is making her smile now.

Will Smith

Pretty sure many people are a fan of The Fresh Prince, who is better known as Will Smith. To some degree, the star has tried his hand in various parts of the industry that’s why it would be pretty hard to miss him. He is not only a rapper and actor, but he is also a film producer. Furthermore, no one has surpassed the actor’s amazing feat. He is the only actor that has been in eight straight films that had grossed more than $100 million in the United States box office!

The star has undoubtedly met some of the most amazing and loveliest people in the industry. One of those would be one of his partners at the beginning of his career. For a good three years, he was with Sheree Zampino. Some things don’t work out, and that’s okay. Two years after their split, he married his current partner, Jada Pinkett.

Zoe Saldana

I think many will agree that Zoe Saldana is one of the loveliest females in Hollywood. However, she is also one of the most incredible actresses in the sci-fi realm. She is in the Star Trek film series, the Avatar film series, as well as several movies in the Marvel Cinematic Universe. With her incredible talent and state-of-the-art beauty, it comes as no surprise that several men have fallen in love with her. At the start of her career, she was with Keith Britton. They were together for more than a decade.

However, some love stories don’t end with wedding bells, and the two went their separate ways. Right now, Saldana is with Marco Perego, and they’re currently growing their family. They currently have three children. With parents like Saldana and Perego, I think we could all agree these kids won’t be needing student loans.

Julia Roberts and Daniel Moder

Julia Roberts has been happier than ever with her better half, Daniel Moder, since they walked down the aisle in July 2002. They welcomed their twins, Phinnaeus and Hazel, in 2004, followed by their youngest son, Henry, three years later. The two first met while filming The Mexican in 2001. At the time, Roberts starred as Samantha Barzel, while Moder worked as one of the cameramen.

With her girl-next-door persona and dainty looks, it was only a matter of time before the actress earned the Hollywood title of “America’s Sweetheart.” She was enjoying the peak of her fame in the ’90s to 2000s, all thanks to her string of blockbuster films. Alongside her movies, even her romantic life was booming. Roberts credits her husband as her “favorite human.” Today, they still seem to be content and happy with their marriage.

Jamie Lee Curtis and Christopher Guest

Jamie Lee Curtis and her screenwriter husband Christopher Guest have one of Hollywood’s longest-lasting marriages. Throughout the years, the couple has been supportive of each other in their respective careers and during the good times and the bad. They recently marked their 36th wedding anniversary, and for the occasion, Curtis posted a black-and-white throwback photo of them on social media and wrote a sentimental caption.

When asked about their secret to a happy marriage, the actress had the best answer, saying: “Don’t leave. That’s really it. Do your work, and then let God take over.” According to Curtis, she is as creative as she ever has been in her life, and she and Guest have been spending quality time together. The Hollywood duo has raised two kids, Annie and Thomas, and put up business investments, including the My Hand In Yours company.

Ellen DeGeneres and Portia de Rossi

Ellen DeGeneres and her soulmate Portia de Rossi broke barriers when they exchanged their “I do’s” in August 2008. Since then, the Hollywood pair have inspired others with their unique love story. The twosome first met in 2000 at a party, but it wasn’t until four years later that they would become more than friends.

In 2005, they publicly announced their relationship and made their red-carpet appearance for the first time as an official couple. During the couple’s 2009 joint interview, de Rossi said she was in love with the talk show host from the very first time she laid eyes on her. The duo has no children, and they reportedly wanted to stay that way. While they thought about having investment planning for a bigger family, they ultimately decided that they don’t want kids of their own. They have many pets, though!

Amal Clooney and George Clooney

Hollywood superstar meets human rights lawyer— a modern-day fairy tale that belongs to George and Amal Clooney. If there’s one show business couple who stands heads and shoulders, it’s them. Tinseltown’s golden couple made headlines as soon as they dated and announced their relationship.

For a long time, fans believed that Mr. Clooney would remain the most eligible bachelor, but the actor proved otherwise. Instead, he fell in love with the stunning lady. The two were introduced in 2013 by a common friend and began communicating via email. While filming The Monuments Men, he asked her out on a date. Their romantic dates even went as far as Kenya, where they spent their first vacation together. It was also that moment that the A-list actor was sure that he wanted to marry future Mrs. Clooney. True enough, they tied the knot in September 2014 and later welcomed two kids.

David Beckham and Victoria Beckham

David and Victoria Beckham are undoubtedly one of Hollywood’s most popular couples for many good reasons. They have a long-lasting, adorable relationship, and they went through the wringer together. From raising four kids to navigating their investments and careers in the spotlight, they rely on each other to face whatever adventures life throws at them.

Having been married for over 20 years, the Beckhams’ romance is one for the books. The footballer and Spice Girl got together in 1997 at a soccer game. A year after this encounter, he proposed to her with a marquise-cut ring. They married in July 1999 and said their “I do’s” in front of only 29 guests in Dublin. In 2017, the British power couple secretly renewed their wedding vows, and two years later, they celebrated their 20th anniversary with an exclusive tour of Le Château de Versailles.

Serena Williams and Alexis Ohanian

Tennis queen Serena Williams and Reddit bigwig Alexis Ohanian’s romance began by chance. Ohanian knew little about tennis and Williams wasn’t a Reddit user, but it was nevertheless a match made in heaven. From their A-list-filled wedding to their daughter’s birth, the twosome has weathered many storms in life.

The couple first met in 2015 in the most romantic way possible: they stayed at the same hotel in Rome. The tennis pro and the entrepreneur met by chance while having breakfast. Williams invited her future husband to join her and her friends at the table, and the rest is history. They welcomed their baby girl, Alexis Olympia, in 2017, and since then, they have shared a huge degree of love for their growing family. The athlete once said, “marriage is not bliss,” but then added that it could be “if you work at it.”

Jada Pinkett Smith and Will Smith

Now, this is a story about Will Smith and his wife Jada Pinkett Smith’s rock-solid marriage. As one of Tinseltown’s most iconic couples, the Smiths have raised three kids, celebrated multiple award wins, and went on adventures. They wed in 1997 and have been enduring life’s challenges ever since.

Though the couple has never shied away from sharing the ups and downs of their marriage, their 23-year bond is a testament to how they’ve won many battles despite being in the public eye, including a separation. Smith once revealed that he wasn’t sure if they would even reconcile during this challenging time. To his credit, he persevered against all odds, and so did his beloved wife. They have since proved that they have an “unconditional love for each other.” Their strong bond as a couple was indeed defined by this dark chapter of their relationship.

Kelly Ripa and Mark Consuelos

Actors Mark Consuelos and Kelly Ripa became husband and wife on Labor Day 1996. More than two decades later, their relationship still goes strong. The celebrity pair have since given birth to three children: two sons and a daughter. Whenever they’re not posting cute Instagram photos, the couple speaks candidly about their marriage.

In August 2018, the talk show host explained that she fell in love with the actor at first sight, thanks to the television show All My Children. The two became co-stars on the ’90s series, and they were cast as each other’s love interest, sparking electricity between them. After a year of dating, the twosome eloped in Las Vegas, and they have been inseparable ever since. In celebration of their 20th anniversary, their family went on a trip to Turks and Caicos, and Ripa happily wore her wedding dress.

Tom Brady and Gisele Bündchen

Gisele Bündchen and Tom Brady may appear to be the perfect celebrity couple, but they’ve faced their fair share of major challenges. Their first test came only a few months into their courtship when they learned that Brady’s former girlfriend was pregnant with his child.

More recently, after almost a decade of their union, they faced another roadblock when the supermodel found herself unhappy in her marriage with the NFL player. Instead of allowing these problems to derail them, the couple, however, found a way to overcome and grow stronger. They learned the value of communication, and in fact, Bündchen wrote her husband a heartfelt letter to express what she felt. Brady credits his wife for doing so because it made him understand his responsibilities as a husband and a dad. The couple exchanged vows in February 2009 and have welcomed two kids.

Jaclyn Smith and Brad Allen

Charlie’s Angels star Jaclyn Smith is sure that her husband Brad Allen is heaven-sent. The actress and the cardiothoracic surgeon have been a married couple since 1997, and until now, they are still happily in love. As Smith said, she’s still a “lucky girl” despite over twenty years of marriage. They are also determined to bond over their similar interests.

The couple likes to go to places they have never been. For them, going the distance works great because they build memories together no matter how much gas it costs! Smith met Allen at a hospital in Houston. He had operated on her father, and the two easily became smitten with each other. “I saw a purity of heart,” the actress spoke of her husband. Since their union, she has insisted that Allen’s the man she had always dreamed of.

Oprah Winfrey and Stedman Graham

Oprah Winfrey is undoubtedly one of the most highly recognizable women on the planet. Her longtime romance with Stedman Graham, however, has been kept low-key. The two met at a charity event way back in 1986, and since then, he has been the main man in the media mogul’s life for over 30 years. While they opted not to marry, their bond and commitment go beyond contracts and papers.

The couple said that walking down the aisle would only complicate things, saying that their romance wouldn’t have lasted if they were married. Nevertheless, Graham has always been by Winfrey’s side through ups and downs, especially during her heyday. Since increasing her Hollywood credit score, she has also not forgotten how the businessman took care of her and prioritized their relationship. Well, they may not be married legally, but they are definitely married by heart.

Keith Urban and Nicole Kidman

Actress Nicole Kidman and musician Keith Urban have been together for about 15 years, which, in Hollywood language, is roughly equivalent to a lifetime. Despite their successful careers in the limelight, the two have managed to keep their long, dedicated relationship private. Still, whenever they walk on the red carpet together and post about each other on their social media accounts, it’s crystal clear that they are meant for each other. The couple was able to transform their instant connection into long-lasting love, from their first meeting to the degree of adversities they have faced.

The lovebirds first met at a 2005 event and quickly fell for each other. The following year, they tied the knot in a romantic ceremony in Australia. The couple has two kids, Sunday Rose, born in 2008, and Faith Margaret, who was born via surrogacy in 2011.

Sarah Jessica Parker and Matthew Broderick

Actors Sarah Jessica Parker, or SJP, and Matthew Broderick bonded over their shared love of the musical theater in the ‘90s. Nearly 30 years after meeting, the two are still keeping their love alive. SJP met Broderick through the world of Broadway in November 1991. She was introduced to her future husband thanks to her brothers, Toby and Pippin, who helped start their theater company in New York. It wasn’t until several months after they first crossed paths that the Ferris Bueller’s Day Off star asked the SATC actress on a date.

The Hollywood pair walked down the aisle in 1997 and welcomed their first child, James, in 2002. Seven years later, they became doting parents to twin girls, Tabitha and Marion, via surrogate. The two stars have kept their relationship and home security intact as possible throughout their romance.

Jason Momoa and Lisa Bonet

If it isn’t clear enough already, Lisa Bonet and Jason Momoa have a great romance that is hard to beat. The Cosby Show alum and the Aquaman star have been together for nearly 14 years. The two are relatively private, but they have given us tidbits throughout the years to put together an overview of their relationship.

Momoa said he knew he and the actress were right for each other when he first saw her on the small screen when he was 8, but they didn’t officially meet until the mid-2000s. Their first encounter happened at a jazz club. Fast forward to years later, the lovely couple managed to raise a blended family, sustained their happy relationship, and made secure investments in their acting careers. In 2014, Momoa and his stunning wife starred alongside each other in their first film, Road to Paloma.

Gabrielle Union and Dwyane Wade

When an A-list actress and an NBA star come together, you get one of Tinseltown’s most iconic couples. Gabrielle Union and Dwyane Wade have been married for six years, but they have been together for a total of 13 years already. They first met in 2007 at a Super Bowl party, but soon after they began dating, they waited two years to reveal their relationship to the public.

In 2013, Wade proposed to the star with the help of his children. Eight months later, they exchanged “I do’s” in Miami. Union became a stepmom to her husband’s kids from his past relationships, and together, they are parents to their daughter Kaavia James. Their commitment to each other and to their children deserves a lot of credit. Recently, the power couple landed on Time Magazine’s list of 100 Most Influential People. Needless to say, their partnership is ahead of the game.

John Mulaney and Annamarie Tendler

Anyone who has seen any of John Mulaney’s Netflix comedy specials in the last decade is familiar with his partner, Annamarie Tendler. The comedian has often joked about his romance with Tendler onstage, teasing her brutal sincerity and misinterpretation of Leonardo Da Vinci’s The Last Supper, as well as praising marriage.

Mulaney and Tendler have regularly collaborated on projects since their first meeting in the late 2000s, including the Broadway show Oh, Hello! and fundraising for various causes. According to many fans, the West Village-based couple seemed to have an artistic, collaborative, and strong bond. The two met through respective friends while vacationing in Massachusetts. They weren’t dating at the time, but Tendler had a feeling they would be soon. They tied the knot at the Onteora Mountain House in July 2014. They spoke about their career investments, their mates, and Petunia, their French bulldog. Sadly, Mulaney and Tendler recently announced their split nearly seven years after their beautiful 2014 wedding.

Tim McGraw and Faith Hill

Tim McGraw and Faith Hill are music’s most famous couples, with one of the industry’s longest marriages. The country stars have collaborated on award-winning music investments over two decades, not to mention three children.

Their romance began in 1994, when they met in — where else? — Nashville! The two rising stars of country music were performing at the annual Country Radio Seminar in Music City, U.S.A. at the time. Still, their relationship didn’t blossom for another few years. Though they got along swimmingly at the case, they both claim that nothing more than casual occurred. Faith accompanied Tim on his Spontaneous Combustion Tour two years later. Sparks flew, and Hill followed her heart this time. She ended her engagement to start a relationship with McGraw. After a few months on tour together, he told her he wanted to marry her. Whether they’re playing on stage together or cuddling close off-camera, they have a lot of chemistry. Perhaps it’s because, as the two celebrities have said, their marriage is their top priority.

Rick Harrison and Deanna Burditt

Pawn Stars is an exciting reality show that follows the everyday activities of Gold and Silver Pawn Shop in Las Vegas and airs on the History Channel. The Harrison family, which includes Richard “The Old Man,” Rick Harrison, and Cory “Big Hoss” Harrison, owns the shop and assists customers with consumer credit. If you’re a frequent viewer of Pawn Stars, you’ll know that Rick is the show’s main character. He inspects the products to ensure their consistency and validity. On the other hand, his love life has never been a significant plot point on the show.

Deanna Burditt is Rick’s wife. Her profession and ambitions are still unknown to the general public. The pair got engaged in 2012 and took their love to a greater degree a year after. Even though Rick has become a reality star in his own right, Deanna refuses to be in the spotlight, with him claiming that his wife “has no desire to be famous.” Deanna seems to have succeeded in keeping her life private.

Barbi Benton and George Gradow

Country music emerged in the 1920s, influenced by folk and blues music. Several television shows focused on the genre, but Hee Haw was doing it long before it was even a thing. The show featured comedy skits and a heavy emphasis on country music, and Barbi Benton conquered it all. She dominated the 1970s as she forged her degree in Hollywood, thanks to her performance in both worlds.

Benton rose to prominence due to her satirical acting roles in the show’s numerous comedy sketches. After becoming a household name, the young actress received acting offers, including her first film role. Aside from her career success, she also found luck with George Gradow. He had fallen in love with her from seeing her on television. Fortunately for Gradow, his friend’s mother knew Benton’s mother and set up a date for the two – and, as they claim, the rest is history!

Denise Austin and Jeff Austin

Many ideas come to mind when you hear the word “fitness.” One of which is most definitely Denise Austin, a well-known fitness instructor. Austin spent two terms on the President’s Council on Physical Fitness and Sports and helped introduce the MyPyramid system in America. That, along with her other accomplishments, contributed to her decades of fitness career.

Talking about her personal life, Denise married Jeff Austin, a former American professional tennis player, in April 1983. Her life has changed in significant ways as time has passed. Her daughters relocated to Los Angeles. She and her spouse chose to downsize from their investment home in Virginia to a Manhattan Beach condo to spend more time on the west coast. Denise has kept her marriage secure since marrying Jeff. This couple seems to have maintained their love after over three decades of bliss and two children.

Jennifer Love Hewitt and Brian Hallisay

Jennifer Love Hewitt keeps a low degree when it comes to her personal life, but there’s no denying she’s ecstatic to be a wife and mother to her lovely family. She met her loving husband, Brian Hallisay, while on the set of Love Bites in 2011. Even though their relationship was limited to costars, they reconnected on the set of The Client List in March 2012. Given that their characters on the show were exes, it’s almost hard to believe they fell in love so quickly.

As viewers followed their romance on the hit Lifetime drama, their relationship grew even stronger off-screen. Hewitt revealed she was pregnant just a year after the couple’s relationship was first publicized. They became the happy parents of their eldest child, Autumn, only days after marrying in a private ceremony in November 2013. In June 2015, the happy couple welcomed a new addition to their family: son Atticus. When they aren’t working together or caring for their children, they make the most of whatever free time they have together.

Jay Leno and Mavis Leno

Jay Leno is a man of many things. He is well-known for his humor, vintage car collection, and friendships, but did you know he’s been married for decades? After more than 40 years since they first met, Jay and his wife, Mavis Nicholson-Leno, are still deeply in love, and the host has revealed his secret to a long and happy marriage.

They met by fate. Mavis went to The Comedy Store to watch up-and-coming comedians. She wasn’t looking for love; in reality, her visit to the world-famous comedy club was strictly professional. Friends had told her that Mavis might make business contacts at the popular comedy venue as a blogger. She confronted Jay, and the rest, as they say, is history. However, their path to marriage was not incredibly romantic. The legendary comedian claimed that he had purchased an insurance policy and wanted Mavis to be covered if anything happened to him. Indeed, the pair need no great show to prove their love.

Heidi Klum and Tom Kaulitz

The stunning Heidi Klum moved on fast, marrying a man with whom many of us are unfamiliar. He is Tom Kaulitz. While Kaulitz isn’t well-known to some degree, he is a star, so the supermodel’s new husband is more than just a pretty face. Remember Tokio Hotel, the rock band from the early 2000s? Kaulitz is the guitarist for the German pop-rock band.

It was 2018 when many saw her kissing Tom on America’s Got Talent set. Klum was not only a judge on that competition, but she was also the host of Germany’s Next Top Model. They met through a mutual buddy who worked on the show. They soon made their love red carpet official and wasted no time setting the groundwork for their future. With their compatibility, the couple only dated for a few months before secretly marrying. Despite their considerable age gap, the two are a match made in heaven. The two are free-spirited individuals who share a mutual zest for life.

Salma Hayek and Francois-Henri Pinnault

Salma Hayek is open about how smitten she is with her husband of 12 years, François-Henri Pinault. The actress surprised fans by announcing in 2007 that she was engaged and expecting a child. She and her fiancé welcomed their daughter Valentina Paloma in September 2007, and on Valentine’s Day 2009, they married peacefully in Paris.

Pinault’s resume is imposing. He is the CEO of Kering, a luxury retail conglomerate that owns big fashion labels such as Saint Laurent and Gucci. They also run Groupe Artémis, the Pinault family’s investment firm, which owns everything from Château Latour in France to Christie’s, the world’s most well-known auction house. Hayek met her future husband when she was 39 years old, and she admitted that she was worried she’d never find The One. Despite their firm belief that a balanced work-life balance is possible and that freedom can hinder a happy marriage, Hayek and Pinault make it a point to put each other first.

Pat Sajak and Lesly Brown

When we think of Pat Sajak from the Wheel of Fortune, his on-screen sidekick Vanna White always comes to mind. Many watchers might be unaware that the TV symbol is a typical family man when he is not on stage. Though Sajak has been hosting the show with White for decades, their relationship is strictly personal, and he is happily married to Lesly Brown.

Their tale begins in 1988, when they met through a mutual friend at a restaurant opening in Irvine, California. Although they were on opposing surfaces of the world, Sajak and Brown kept in contact. They talked on the phone a lot, but their relationship started as a friendship. Sajak eventually popped the question to Brown, and on New Year’s Eve in 1989, they married at Saint Mary’s Roman Catholic Church in Annapolis, Maryland. Brown has decided to forego her ambition of becoming a lawyer to be a stay-at-home wife. After 32 years of marriage, they are proud parents to two adult children.

Hugh Jackman and Deborra-Lee Furness

Hugh Jackman is eternally thankful that he was 100 percent certain about everything at least once in his life. The actor and Deborra-Lee Furness have been married for over two decades and are still going strong.

In 1995, the two actors met while filming a TV drama called Corelli in Australia, and Jackman was immediately smitten. Even though Furness needed some persuasion, she soon realized their love was meant to be. The pair wedded less than a year later and have been together ever since. They later adopted twins, Oscar Maximilian and Ava Eliot, and watched Jackman’s degree take off and reach A-list status along the way. However, neither success nor time has tarnished their relationship. Jackman and Furness are still prime examples of what true love looks like today. He has made it clear that he will continue to define “soulmate” for his spouse. He adhered to the “happy wife, happy life” mantra, which is commonplace to repeat but complicated for many movie stars to practice.

John Legend and Chrissy Teigen

Chrissy Teigen and John Legend have climbed to the highest degree of the Hollywood power couple ranks in recent years, thanks to their extensive talents, funny online personas, and adorable children.

Years before Teigen and Legend became one of Hollywood’s most notable celebrities, they met on Legend’s music video for Stereo in September 2006. Teigen played the object of Legend’s affection. After a 14-hour shoot, the two ended up eating In-n-Out burgers in his hotel room. Fortunately for Teigen, the humor and beauty that her fans adore are what made Legend fall in love with her. The singer popped the question to her in December 2011 during a trip to the Maldives for Christmas. Two years after they met and three months after appearing in the music video for one of Legend’s biggest hits, All of Me, the couple married. Legend wrote his new song, Never Break, to honor his unbreakable love for his wife.

Pierce Brosnan and Keely Shaye Smith

Only a man who genuinely loves and respects his woman will praise and thank her. Somebody like Pierce Brosnan is a blessing in today’s world, where loyalty and gratitude are in short supply. The actor, who has been married to Keely Shaye Smith since 2001, claims that there is no one more suitable for him.

The James Bond actoar coincided with his future wife when he was going through a difficult time in his life. Brosnan was blown away by the woman, and he confessed that he couldn’t get enough of her on their first date. The pair conversed for hours, and he knew that destiny brought them together. They dated for seven years, and their perception of one another improved with each passing day. They married and began a family together. While Brosnan is known for his fame and career investments, Smith is his one-of-a-kind discovery and priceless gift.

Jessica Simpson and Eric Johnson

Jessica Simpson and Eric Johnson freshly marked ten years of marriage and a love that seems to be greater than ever. Johnson earned his degree of fame as a former NFL player who played for the San Francisco 49ers and New Orleans Saints. When the 40-year-old Yale alum met the singer, he dropped out of the University of Pennsylvania’s Wharton School to be with her. After six months of dating, the former athlete proposed to the singer in November 2010, but the pair didn’t walk down the aisle until 2014.

In the same way that Simpson appears to have found Mr. Right in terms of love and family values, she seems to have found the one in terms of privacy. Johnson hasn’t spilled a single iota of detail about their personal life in public, despite remaining an amiable and photogenic presence at events and on Instagram with his wife and kids.

Joel Osteen and Victoria Osteen

Joel Osteen rose to a prominent degree as one of the world’s most well-known and influential televangelists today. After televising his sermons, the pastor gained a following of nearly 10 million weekly viewers in the United States alone. Aside from that, Joel is well-known in the media for his long-term marriage to his wife Victoria.

They are the epitome of a happily married couple. The Lakewood Church’s co-pastors have been married for more than three decades and are still going strong as husband and wife. He went in to buy a watch battery when he met Victoria. The couple began dating soon after their first meeting and married two years later. For a time, the couple assisted Victoria’s father as he traveled worldwide, spreading the ministry. The two have been together for more than three decades. Of course, they have had their share of ups and downs along the way, but they’ve never let minor misunderstandings derail their relationship.

Warren Beatty and Annette Bening

Warren Beatty and Annette Bening are one of Hollywood’s celebrity couples who are still together. Known for their acting chops, it is not surprising that they have several investments to their name. They first met on the set of Bugsy and they just hit it off. They have four children between them who are all grown up and are successful in their own careers. For Beatty, it took him only a few seconds to realize that Bening was The One for him.

The Siege star told in an interview that there was no secret to their lasting marriage. The couple tied the knot in 1992 and their love is still going strong. Beatty recalled that he lost interest in the food that he was eating while on a date with Bening, and it seems he is still smitten with his gorgeous wife. Her most recent work was in the movie Captain Marvel, which the actor is quite proud of.

Sam Elliott and Katharine Ross

Sam Elliott has established himself as an actor who plays cowboys, bikers, and military men. But that gruff exterior and drawl may have helped him win the heart of his co-star in The Legacy, Katharine Ross. The actress has quite a career where she appeared in several movies like The Graduate, Butch Cassidy and the Sundance Kid, and The Stepford Wives. Elliott admitted that he didn’t talk to Ross during the shooting of Butch Cassidy and the Sundance Kid because he was just a glorified extra.

It was in the film The Legacy where sparks flew between them and soon, they were already married. Ross was supportive of her new husband and was the one who made sure that he got in the casting call for the film Mask, in spite of their being on their honeymoon. The couple’s net worth is enough to ensure that they don’t have to apply for personal loans in the long run.

Elton John and David Furnish

Elton John is a British music icon who has wowed the crowd with his songwriting skills and knack for entertainment. What endeared him to many is his relationship with David Furnish, whom he met back in 1993. They went on a date and the rest was history. John and Furnish married after being engaged for 9 years and as soon as gay marriage became legal in the UK.

The two are couple goals to be exact as they are very much supportive of one another. When not busy with his music, the couple loves doing philanthropy work using their investment money to assist charities. The multi-awarded singer stated that they are constantly working on their marriage, which helped them make their bond stronger. They have also grown their family by two after having babies via surrogate. They are the picture of a perfect family with their sons beside them.

Jodie Foster and Alexandra Hedison

Jodie Foster and Alexandra Hedison have been married since 2014, after a year of being together. Everyone sure knows who Jodie Foster is. She is one of the A-list stars in Hollywood, not to mention an award-winner who took home some of the most major awards in the entertainment scene. The 58-year-old actress gets credits from some of the most iconic films of today, like The Silence of the Lambs and Taxi Driver, among others, but what about her wife?

Just like Foster, Hedison is an equally high-profile celebrity. She is an actress known for her role as Dylan Morehead on The L Word. She is also a famous photographer in the US. Her works have been on display in New York and Los Angeles, which probably made Foster proud. Did you know Hedison once dated Ellen DeGeneres? Yep, these two had been together for three years and ended their romance in 2004.

Michael Douglas and Catherine Zeta-Jones

Age is but a number between Hollywood stars Michael Douglas and Catherine Zeta-Jones. What’s important is that the two have managed to stick to their marriage after all these years. The Chicago star admitted that their marriage had its highs and lows, but what made them push through is their sense of humor and fun. They have managed to stay out of the limelight while raising their two children which is one of the reasons why they stepped back from acting for a bit.

With more than two decades into their marriage, it is clear that they have good financial advisors to help them manage their wealth. Needless to say, they are doing fine in terms of income. With their kids all grown up, there is a good chance that we will see more of them on films. The two have been sharing their love for one another through their respective social media accounts, and they couldn’t be more adorable!

Ronda Rousey and Travis Browne

The name Ronda Rousey is known in the WWE arena, and is often associated with body slams and arm bars. However, after her last defeat, the sports celebrity seemed to have stayed out of the cameras for a while right into a farm. Many were surprised by this move as she is already earning millions for her skills on the ring. Well, mixing farm life with married life may be one of the lures for Rousey to take a step back from her career and we dig it!

She married her long-time boyfriend and UFC Fighter, Travis Browne, in 2017 and it seems that they have transitioned well into a farm life. According to Rousey, her husband wakes up at the break of dawn to work out then tend to the farm. She cooks their breakfast before taking over the chores. The couple’s investments on their farm is for the future of their children as they are aiming for a sustainable living.

Matthey McConaughey and Camila Alves

Matthew McConaughey and Camila Alves are a picture-perfect couple who has been married since 2012. It was love at first sight for the actor after seeing the model across the room in a bar. His friend, Lance Armstrong, had to be the wingman to introduce the two. After they started dating, the A Time to Kill star wanted to continue their relationship. Though the model did not have any plans to getting married, she eventually said yes to the actor. Today, they have three children between them and are currently homeschooling them in Texas.

McConaughey is all praises to his wife after winning an Academy Award for his performance in the Dallas Buyers Club. Alves, on her part, has been managing his home and their children with great success. It is no wonder that the Hollywood star can’t help but fall in love with her again and again! For sure, their financial adviser has been helping them with their finances, especially after building their Malibu mansion.

Matt Damon and Luciana Barroso

The Bourne Identity icon Matt Damon was simply drawn to Luciana Barroso the first time they met in a bar, where she was working as a bartender. Though he did turn up the charm on her, Barroso made him work especially when he tried to hide behind her bar. What endeared the actor to her was the fact that he accepted her being a single mother. It seems the stars have aligned and their chance meeting was more than that.

Today, the couple are still very much together and busy raising their children. Many have been wondering how they managed to make their marriage work while Damon was a Hollywood A-lister and Barroso was a regular gal. Damon stated that this was what exactly made their marriage work because when he gets home, his focus is on his family and nothing else. It helps too that their investment money is being put to good use in raising their children well.

Elisabeth Shue and Davis Guggenheim

Elisabeth Shue has made a name for herself in Hollywood since the ‘80s. She appeared in various films like The Karate Kid, Adventures in Babysitting, and Back to the Future, where she replaced Claudia Wells as Marty McFly’s girlfriend. Her husband, Davis Guggenheim, has been her silent partner ever since they tied the knot. The producer and documentary filmmaker is known for his work in The Shield and Deadwood. It was his work in An Inconvenient Truth that earned him an Academy Award.

Shue is not the only one who has been earning well. Guggenheim has also amassed quite a fortune thanks to his documentary work. Their net worth, when combined, is jaw dropping which means that they don’t have to worry about mortgage payments or any monetary issues for that matter. The couple still work on their marriage outside of work, which is one of the reasons why they are still together even today.

Phoebe Cates and Kevin Kline

Phoebe Cates was one of the most sought-after stars back in the ‘80s. She appeared in various films like Gremlins and Fast Times at Ridgemont High. Though many were interested in her personal life, fans were shocked when she married French Kiss actor Kevin Kline, who was older than her. Fortunately, the actress followed what her heart was saying as they are still together even today. Kline was worried at first about their age gap and their differences, but they did manage to make their marriage work.

The couple became parents in 1991. They welcomed their second child three years later, and they couldn’t have been happier. Cates was the one who took a step back from acting as she preferred to stay with her children. She has put her own investment money on a boutique for her clothing. Being a business owner has suited the quiet actress.

Tom Hanks and Rita Wilson

The love story between veteran actor Tom Hanks and fellow actor Rita Wilson is one for the books. Like with many Hollywood couple, they met on the TV set of Bosom Buddies. However, Hanks was still married to his first wife back then, but there was no denying the instant connection between the two. The two got married in 1988 and they have been together ever since. They have three children together, with Hanks having two more from his previous marriage.

You can tell that the power couple knew how to keep their love strong over the years. The couple put a lot of time and effort into raising their children which is one of the reasons why they are doing well. Perhaps they know how beneficial it is to have an investment planning while their kids were growing up because they didn’t have to worry about finances at all.

Goldie Hawn and Kurt Russell

Goldie Hawn is a glowing icon in Hollywood as her versatility as an actress is evident with the characters that she had played. Lucky for her, she found her soulmate in yet another actor in the form of Kurt Russell who has also established himself as well-rounded actor. Even though they aren’t married, they have been together for more than two decades now and it seems that they aren’t tired of each other!

Hawn and Russell have worked together to raise their children both from Hawn’s previous marriage and their own. It is not surprising that Kate Hudson, Hawn’s daughter with her first husband, looks up to Russell. The couple made sure that their children are financially stable on their own. Perhaps they hired a financial advisor to teach them the importance of money for their future. The power couple has since worked on a few films together, with the latest being The Christmas Chronicles.

Adam Sandler and Jackie Sandler

Big Daddy star Adam Sandler found romance on the set of the film with his now-wife Jackie. She started out as a model but tried her hand in acting. Her first role was in Deuce Bigalow: Male Gigolo, where she played the character Sally. She later appeared in Big Daddy, where she was a waitress in the bar called Blarney Stone. It was here that their love story began, and they became inseparable. After she converted to Judaism, the couple tied the knot in 2003 and had two children between them.

The couple has since worked together on several films like Just Go With It, Grown Ups, 50 First Dates, as well as Hotel Transylvania. She also appeared in the film Murder Mystery. Sandler has given plenty of credit to his wife for endless support to his career. For the actor, it was Jackie who gave him the confidence to do the things he didn’t know he could do.

Denzel Washington and Pauletta Pearson

Power couple Denzel Washington and Pauletta Pearson first met in 1977 while working on the TV movie called Wilma. The couple dated afterwards while carving their own paths in Hollywood. Denzel has since moved on to become one of Hollywood’s A-listers, but Pearson is not far behind. She appeared in Philadelphia and later in She’s Gotta Have it. It took Denzel three tries before she accepted his marriage proposal, and what a relief it was because they are still together.

Their marriage produced four children, all of whom are interested in the entertainment industry. Both John David and Katia are already acting while their twins are using their degree in filmmaking and acting to carve a name for themselves too. The Washington clan is certainly a name to watch out for in Hollywood. The couple stated that there was no one secret to why their marriage is doing great. Whatever it is that is keeping the magic alive between them, we all hope that it will last a lifetime.

Ringo Starr and Barbara Bach

The personal life of The Beatles drummer Ringo Starr has been quite private compared to his other bandmates. This is why many are asking if he and former Bond girl Barbara Bach are still together. The two met while filming Cavemen. Though the film wasn’t received well, it put the two together. Although their relationship started off on the wrong footing, they were able to get help and remained sober. Their initial trials as a couple probably contributed to the reason why they are still very much together today.

Although they did not have any children between them, their children from their previous marriages became their own. They doted on them and used their investments to raise them well. Starr is still known to make music while his wife remains behind the scenes, keeping house and being the moral support to her husband. Fortunately, they were able to get their heads straight and are enjoying the fruits of marital bliss.

Marie Osmond and Steve Craig

Marie Osmond and Steve Craig’s love story is one for the books. These two have worked with their lawyers to end their first marriage in 1985. After parting ways for about 27 years, Osmond tied the knot with another man, while Craig remained single. Thanks to their child, the two reconnected, which paved the way for them to try another shot at love.

Osmond tried to hide their rekindled romance for a couple of years, thinking it might not work out again, but the opposite happened. The couple got married again in 2011, and no one expected it would happen. To make this once-in-a-lifetime moment more special, Osmond donned the wedding dress she wore on the first time that they exchanged vows in 1982. Despite being separated for more than a couple of decades, Osmond confessed she loves being with Craig.

Justin Timberlake and Jessica Biel

Justin Timberlake and Jessica Biel have been defying the negative connotation that comes with Hollywood marriage. Despite the degree of rumors about their union, their love remains strong, resulting in more than a decade of togetherness. The couple, in fact, continuously posts sweet photos and videos of them together on social media, honoring each other with their heartfelt quotes and captions.

Their love began when Timberlake and Biel first met at a birthday party the singer-songwriter threw in 2007. He quickly asked for her number and invited her on a date, and after that, they made their relationship public in the same year. Although they parted ways in 2011, they rekindled their romance after just a few months and quickly got engaged. In 2012, Biel walked down the aisle. They are now blessed with two kids, Silas Randall and Phineas Timberlake.

Samuel L. Jackson and LaTanya Richardson

You can give Samuel L. Jackson a lot of credits for being a great actor, but you will surely praise him for being a one-woman man. Despite the many temptations Hollywood has, the iconic star manages to be faithful to the woman he loves, LaTanya Richardson. The two have been married since 1980. This only means they have been devoted to each other for more than four decades.

Long before they became a couple, Jackson and Richardson already knew each other. They met when they were only college students in Atlanta, Georgia. Though they didn’t belong in the same class, fate had brought them together. What’s the secret to their more than 50-year-old romance? Richardson said they never dared to go to bed angry at each other. Even if she is mad, she will say goodnight to Jackson and tells him she loves him.

Winona Ryder and Scott Mackinlay Hahn

If you think Winona Ryder is single, no, she is not. The 49-year-old actress has been in a longstanding relationship with the shrewd businessman Scott Mackinlay Hahn. The two have been together since 2011, and don’t be surprised if not too many people know about it. Why? The couple has been notoriously private about their romance. They are both keeping low profiles, which may be their secret to their decade-old relationship.

Despite their silence, Ryder and Hahn are still major couple goals. Fans can see them together walking the red-carpeted flooring of major events, looking like the perfect pair that they can ever see. No wedding bells for them yet, however. Though the actress has admitted she is a serial monogamist, she is not sure about marriage. She will instead choose not to be married than to undergo the bloody process of getting legally separated.

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