We Forgot These Celebrity Couples Even Dated In The Past
Most celebrities want to be known for their talent, but it often depends on who you are dating and when you are dating them. The media is thrown into a frenzy when two huge stars team up. Every sighting and photo of the couple is watched by the entire world. Relationships in the City of Dreams, however, are doomed by the “Hollywood Curse.” However, these celebrities are mistaken if they believe we will forget about their previous relationships. We’re about to refresh your memory with some of the most well-known celebrity relationships from the past that you might have forgotten about.
Nicole Kidman and Lenny Kravitz
Nicole Kidman and her singer-husband, Keith Urban, are known for their intense PDA. Kidman was previously engaged to musician Lenny Kravitz before meeting Keith, and even before meeting Tom Cruise.
Nicole Kidman and Lenny Kravitz
The former couple was engaged in 2003, but the Stepford Wives star later explained that she “wasn’t ready” to marry, so the couple never married. Nicole Kidman, on the other hand, has gone on to star in the hit series Big Little Lies alongside Kravitz’s daughter, Zoe.
Sandra Bullock and Matthew McConaughey
Sandra Bullock and Matthew McConaughey began dating after appearing together in the film A Time to Kill. It’s difficult to recall a time when McConaughey wasn’t married to Camilla Alves, and the couple was admired for their beautiful romance as well as their stunning looks.
Sandra Bullock and Matthew McConaughey
Even so, four years before they married, McConaughey told Playboy about his romance with Bullock, saying, “She’s not a little girl. She’s a woman,” expressing his admiration for his then-fiancée, adding, “She could run a country.”
Ryan Reynolds and Alanis Morissette
On their respective social media pages, Ryan Reynolds and his current wife, Blake Lively, have proven they are “couple goals.” The Deadpool actor dated Alanis Morissette before meeting the Gossip Girl star, marrying her, and having two children with her.
Ryan Reynolds and Alanis Morissette
The two Canadian actors met in 2002 and dated for four years. Reynolds did, in fact, propose to the “Ironic” singer, but the two never married and split up in 2006.
Reese Witherspoon and Jake Gyllenhaal
When Reese Witherspoon’s marriage to Ryan Philippe, the father of her children, fell apart, it was a difficult time for her. Fans, on the other hand, were overjoyed when it was revealed that Witherspoon had begun dating the very handsome Jake Gyllenhaal.
Reese Witherspoon and Jake Gyllenhaal
When the two megastars met on the set of the film Rendition in 2007, sparks flew. They married soon after, but their relationship only lasted two years, as the Big Little Lies star and the Brokeback Mountain actor split up in 2009.
Mila Kunis and Macaulay Culkin
Mila Kunis dated Macaulay Culkin, the star of Home Alone, while she was on That ’70s Show. The couple started dating in 2002 and decided to stay together for eight years.
Mila Kunis and Macaulay Culkin
Kunis recalled telling Howard Stern,“He was huge. You couldn’t walk down the street with him. He always had this weird attraction, like fans just screamed when they saw him!” Since they called it quits in 2011, it appears that the attraction between the two was no longer there.
Leonardo DiCaprio and Gisele Bündchen
We’re still waiting to see which woman can sweep Leonardo DiCaprio off his feet, despite the fact that he’s one of the world’s most famous bachelors. It’s difficult to say because he once dated Gisele Bundchen, the world’s highest-paid supermodel.
Leonardo DiCaprio and Gisele Bündchen
Gisele dated Leo on and off for almost six years before marrying Tom Brady, a top football player. They made a lovely couple, but it was not to last. Perhaps Leo will follow in the footsteps of George Clooney and marry in his 50s.
Blake Lively and Penn Badgley
Even though we previously stated that Ryan Reynolds and Blake Lively were total “couple goals,” the world was once rooting for Blake Lively and her co-star, Penn Badgley. They were not only co-stars on Gossip Girl, but they were also each other’s love interests.
Blake Lively and Penn Badgley
Fans of Gossip Girl rejoiced at the news, as they had gone from an on-screen relationship to an off-screen one. The couple broke up in 2010 after three years of dating, but thankfully, they reunited on Gossip Girl.
Bradley Cooper and Renée Zellweger
Bradley Cooper has been off the market since 2015, despite being on everyone’s radar. He was previously dating actress Renée Zellweger before meeting his current girlfriend and child’s mother, Irina Shayk.
Bradley Cooper and Renée Zellweger
They met on the set of the 2006 thriller Case 39, but started dating after the film’s release in 2009. After months of speculation in the media about their relationship’s status, the couple refused to speak about it, opting instead to make public appearances together. The former couple called it quits in 2011.
Lindsay Lohan and Samantha Ronson
Lindsay Lohan dated Hard Rock Cafe heir Harry Morton in 2006 after her relationship with That ’70s Show star Wilmer Valderrama ended. Following their breakup, the star of The Parent Trap was linked to Samantha Ronson, a British DJ.
Lindsay Lohan and Samantha Ronson
The actress and the musician began dating in 2008, but their high-profile relationship ended in 2009. Lohan previously stated in an interview with Us Weekly that her relationship would not last because “Two toxic people cannot be together. End of story.”
Angelina Jolie and Jonny Lee Miller
Angelina Jolie has made her fair share of news headlines over the years as a result of her relationship choices, as well as her scandals and affairs. Jolie was married to Jonny Lee Miller before her high-profile marriage to Brad Pitt, her Mr & Mrs Smith co-star.
Angelina Jolie and Jonny Lee Miller
The former couple met on the set of their film, Hackers, in 1995, just like her and Pitt. A year later, in March 1996, they married, but three years later, in 1999, they divorced.
Michael Keaton and Courtney Cox
Courtney Cox is best known for her role as Monica Geller on the hit sitcom Friends, but she was in a relationship with Michael Keaton before becoming one of the most well-known and highest-paid actresses for this role.
Michael Keaton and Courtney Cox
In fact, before splitting up in 1995, Keaton and Cox dated for over six years. She married David Arquette a year later, just one year after her first appearance as a leading character on the NBC sitcom. They have one child together, but they are no longer married.
Sarah Jessica Parker and Robert Downey Jr.
Sarah Jessica Parker has nothing but kind words for her current husband, Matthew Broderick, but she had another serious relationship before meeting her soulmate. In fact, before their relationship ending in 1991, the Sex and the City star dated fellow actor Robert Downey Jr.
Sarah Jessica Parker and Robert Downey Jr.
The couple had been together for seven years before calling it quits, and the actor’s struggles with substance abuse at the time were the turning point for their painful breakup.
Kim Kardashian and Nick Cannon
Kim Kardashian is now married to Kanye West, a rapper and singer, and the world is watching her and her family’s every move. Kim was trying to keep up with Nick Cannon before we were all watching Keeping Up with the Kardashians.
Kim Kardashian and Nick Cannon
The couple started dating in September 2006, before Kim Kardashian became one of the world’s most famous women, but the relationship only lasted four months. In January 2007, the couple called it quits, and Cannon went on to marry and divorce Mariah Carey.
Michelle Rodriguez and Zac Efron
When Michelle Rodriguez and Zac Efron were rumored to be dating, everyone thought they were an unlikely couple. Rodriquez is ten years older than the High School Musical star, so this relationship was unexpected.
Michelle Rodriguez and Zac Efron
They proved everyone wrong by dating for only two months before ending their relationship on a “very mutual” basis. Perhaps it had something to do with the fact that Rodriguez began dating model Cara Delevingne the same year.
Orlando Bloom and Kate Bosworth
Most girls swoon over Orlando Bloom whenever he appears on screen, but some lucky ladies have had the chance to date the Pirates of the Caribbean star. While he is best known for marrying Miranda Kerr, a beautiful Victoria’s Secret model, in 2010, he was previously married to Kate Bosworth.
Orlando Bloom and Kate Bosworth
The Blue Crush actress had a two-year relationship with the handsome actor before calling it quits in 2005. Kate, on the other hand, is yet another example of Orlando’s fondness for attractive women.
Ben Affleck and Gwyneth Paltrow
Gwyneth Paltrow seems to have been into leading Hollywood men before marrying a successful British singer. While her relationship with Brad Pitt did not work out, she did date Ben Affleck, the actor from the film Good Will Hunting.
Ben Affleck and Gwyneth Paltrow
The famous couple began dating in 1997 and dated for two years until 1999, before briefly reuniting before calling it quits in 2000. “He’s super intelligent and really, really talented and he’s funny,” Paltrow told Howard Stern. “But he wasn’t in a good place in his life to have a girlfriend.”
Mark Ronson and Rashida Jones
Rashida Jones was once attracted to Mark Ronson, who is known for producing hits like Bruno Mars’ “Uptown Funk” and Amy Winehouse’s “Valerie.” From 2002 to 2004, Ronson and Jones dated and were even engaged.
Mark Ronson and Rashida Jones
After a year together, Ronson proposed to the actress by making a crossword puzzle with the words “Will you marry me?” Their engagement lasted a year and was called off at the same time as their relationship.
Usher and Rozonda “Chilli” Thomas
Usher and Rozonda “Chilli” Thomas were both big names in the early 2000s because of their singing careers, but they became a power couple when they started dating. The singers started dating in 2001, and Rozonda even appeared in Usher’s “U Got It Bad” music video that year.
Usher and Rozonda “Chilli” Thomas
Even so, the couple was said to have broken up in 2003 due to Usher’s infidelity, despite the TLC singer claiming, “We broke up because I guess it was that time or whatever.”
Justin Timberlake and Jenna Dewan-Tatum
Jenna Dewan may have been in one of Hollywood’s most famous marriages before splitting with her ten-year husband, Channing Tatum, but she was linked to Justin Timberlake before she even met her ex-husband.
Justin Timberlake and Jenna Dewan-Tatum
Jenna was a backup dancer for Justin Timberlake’s “Cry Me a River” singer in 2002, which was also the end of Timberlake’s relationship with Britney Spears. “We dated…yeah,” Jenna told Andy Cohen. “We were like friends that then dated….I was not the rebound!”
Brad Pitt and Shalane McCall
This isn’t the first time Brad Pitt has appeared on this list, and it won’t be the last. But, given his ‘ladies man’ reputation, that shouldn’t come as much of a surprise.
Brad Pitt and Shalane McCall
In any case, he’s pictured with Shalane McCall, a (now) former child actress and model best known for her role as Charlotte “Charlie” Wade on the CBS prime-time soap Dallas. Pitt landed a four-episode stint on Dallas in 1987, when he was 24 years old, and met 15-year-old McCall, with whom he began an eyebrow-raising relationship.
Seal and Tyra Banks
Seal’s high-profile marriage to model Heidi Klum is likely to be remembered by many. However, the singer dated another top supermodel before meeting the German beauty. Seal has a thing for models, as evidenced by his brief relationship with Tyra Banks in 1996.
Seal and Tyra Banks
While Tyra Banks has not had much luck with love since their brief romance, Seal married Heidi Klum in 2005 and their marriage lasted nine years before they divorced in 2014.
Scarlett Johansson and Jack Antonoff
Jack Antonoff dated Scarlett Johanson before he began dating Girls actress Lena Dunham. In fact, when they were 17 and in high school, the two actors dated for two years. Furthermore, in 2002, the teenage sweethearts attended prom together.
Scarlett Johansson and Jack Antonoff
For the exes, things are very different these days, and while Antonoff’s relationship with Lena recently ended, Scarlett has been married twice and divorced. In 2011, she divorced Ryan Reynolds, and just last year, she divorced Romain Dauriac after three years of marriage.
Aubrey Plaza and Michael Cera
In 2010, Michael Cera began dating Aubrey Plaza, his Scott Pilgrim vs. the World co-star. The actors dated for over a year before breaking up, but Plaza later opened up to Vulture about their relationship.
Aubrey Plaza and Michael Cera
She recalled, “We drove across the country after we shot that movie and almost got married in Vegas.” Aubrey began dating Jeff Baena a year later, and the two have been together ever since, so Michael Cera appears to be out of the picture.
Ryan Gosling and Sandra Bullock
Sandra Bullock was rumored to be dating Ryan Reynolds in 2011, but this would not be the first Ryan in her life. In fact, in 2002, the Miss Congeniality actress had a one-year relationship with fellow actor Ryan Gosling.
Ryan Gosling and Sandra Bullock
Not only because they were both big names in Hollywood, but also because their romance became public after they met on the set of Murder By Numbers. Instead, it was their 16-year age difference that drew the media’s attention.
Madonna and Dennis Rodman
Madonna had a high-profile relationship with director Guy Ritchie, and when their marriage came to an end in 2008, their divorce was even more public. But there was Dennis Rodman before Ritchie.
Madonna and Dennis Rodman
In 1994, the singer of “Papa Don’t Preach” dated the basketball player for a short time. This was after his divorce from Annie Bakes, and since then, the retired basketball player has married and divorced twice more.
Cameron Diaz and Jared Leto
From 1999 to 2003, actress Cameron Diaz dated 30 Seconds To Mars frontman Jared Leto. The former couple was even rumored to be engaged during this time, with Diaz reportedly wearing a $15,000 engagement ring to the Golden Globes in 2003.
Cameron Diaz and Jared Leto
However, it appears that the couple was heading in the opposite direction that same year, and they have since gone their separate ways. Before marrying Benji Madden, Diaz had a string of relationships, and Leto is still single.
Kate Hudson and Alex Rodriguez
Alex Rodriguez has dated Jennifer Lopez since 2007, and has been linked to Cameron Diaz and Madonna. However, there was a time when the baseball player dated Kate Hudson, the actress from the film How to Lose a Guy in 10 Days.
Kate Hudson and Alex Rodriguez
In 2009, the famous couple dated for seven months before calling it quits. It had only been a year since his divorce from Cynthia Scurtis, his six-year wife, was finalized. During their marriage, A-Rod and Cynthia had two daughters together.
Lamar Odom and Taraji P. Henson
Apart from his high-profile relationship with Khloe Kardashian, it’s difficult to recall who else Lamar Odom was romantically linked to. While the marriage did not last, it continues to be a topic of discussion in the media due to the basketball player’s unfortunate actions.
Lamar Odom and Taraji P. Henson
Odom, on the other hand, was linked to actress Taraji P. Henson in the past, and she even invited him to a Golden Globes party in 2009. Odom was said to have proposed to Henson in 2009, just weeks before tying the knot with Khloe.
Wilmer Valderrama and Mandy Moore
Wilmer Valderrama has had a number of high-profile relationships, including one with Lindsay Lohan and another with Demi Lovato more recently. However, between 2001 and 2002, the actor from That ’70s Show dated Mandy Moore, the actress, and singer from This Is Us.
Wilmer Valderrama and Mandy Moore
After dating Scrubs actor Zach Braff in 2004, Moore decided to get married to her long-term partner, Ryan Adams, in 2009. Wilmer managed to remain unmarried since the couple’s legal separation.
Tom Cruise and Cher
After telling Andy Cohen that Tom Cruise, the star of Top Gun, was in her “top 5,” Cher may wish she could go back in time. The pair dated briefly in 1985 and didn’t go any further than a fling, so many people may have forgotten about them.
Tom Cruise and Cher
Cher’s marriage to Sonny Bono in the 1970s was more well-known, and Cruise’s relationships and marriages to Nicole Kidman and Katie Holmes were more public than his relationship with the singer.
Nick Jonas and Selena Gomez
It’s difficult to keep track of who Selena Gomez is dating these days: is it Justin Bieber, The Weeknd, or Justin Bieber all over again? Meanwhile, prior to her romances with either of the singers, Gomez dated fellow Disney actor and boyband member Nick Jonas.
Nick Jonas and Selena Gomez
Throughout this time, the Jonas Brothers released “Burnin Up,” which went on to become their first top five hit in the United States, and Gomez appeared in the music video for the song.
Alyssa Milano and Justin Timberlake
Alyssa Milano claims she was the rebound for Justin Timberlake after his devastating break-up with Britney Spears, while Jenna Dewan-Tatum insists she was not. Years later, the Charmed actress admitted that she had a brief relationship with Justin Timberlake in the early 2000s, “Right after Britney broke his heart, I swooped in for the kill!”
Alyssa Milano and Justin Timberlake
Justin Timberlake went on to have a long-term relationship with Cameron Diaz before deciding to tie the knot with Jessica Biel after the pair failed to have a serious relationship.
David Spade and Julie Bowen
E! News describes him as “a bachelor-era George Clooney of the comedy world,” and there’s a good reason for that. The comedic actor, who rose to fame on Saturday Night Live, has had a string of leading Hollywood ladies while in the public eye, but he has yet to settle down with any of them.
David Spade and Julie Bowen
Julie Bowen, the actress from Modern Family, is among the women on this list. When Spade starred on Just Shoot Me! in 2002, the two dated for a year. Ed, as well as Bowen.
Rosario Dawson and Danny Boyle
On several occasions in 2013, Rosario Dawson and Danny Boyle were seen looking more than friends. When rumors began to circulate that the alleged couple had broken up, Rosario spoke to NET-A-PORTER about it.
Rosario Dawson and Danny Boyle
She stated to the publication, “It’s not like we announced our relationship, so it’s not like we’re going to announce our breakup.” In the meantime, the photos spoke for themselves, with the director and actress spending time alone together and appearing closer than friends.
Jamie Dornan and Keira Knightley
He now has the lucrative role of Mr. Christian Grey on screen, but he had already caught the eye of British actress Keira Knightley before he was cast in the film adaptation of the best-selling novel.
Jamie Dornan and Keira Knightley
The lovely couple started dating in 2003 after meeting while filming an ad campaign, but split up in 2005. Both actors were relatively unknown at the time, but have since gone on to international fame, with Keira starring in the hit Pirates of the Caribbean franchise.
50 Cent and Chelsea Handler
50 Cent and Chelsea Handler are perhaps one of the most surprising pairings on this list. Even though she stated in an Oprah interview that “I’m not going to date somebody whose name is a number,” the comedic talk-show host dated the famous rapper in 2010.
50 Cent and Chelsea Handler
Nonetheless, it appears that this man, whose stage name is a number, swept the blonde beauty off her feet, and during their time together, she felt “satiated.” Any romance between the two, on the other hand, was doomed to fail.
Seth MacFarlane and Emilia Clarke
Seth MacFarlane and Emilia Clarke met in 2012 when he created the hit animated sitcom Family Guy and she got to play Khaleesi, Mother of Dragons, on HBO’s Game of Thrones.
Seth MacFarlane and Emilia Clarke
Even so, the unexpected couple called it quits in 2013 after only six months of dating. Meanwhile, Clarke was named the most attractive woman in the world by AskMen readers a year later, as well as Esquire’s Sexiest Woman Alive in 2015, so Seth appears to have missed out big time.
Scarlett Johansson and Sean Penn
Scarlett Johansson and Sean Penn made headlines in 2011 when they made their relationship public. Their romance sparked outrage due to their significant age gap, with Penn being 50 at the time and the Lost in Translation actress being only 26.
Scarlett Johansson and Sean Penn
After five months together, however, reports surfaced that Sean Penn “did not want to be tied down” to Scarlett and thus ended their relationship. According to additional reports, Johansson attempted but failed to reignite the romance between the two.
Simon Cowell and Carmen Electra
Music mogul Simon Cowell dated former Playboy model Carmen Electra for a brief period in December 2012 to February 2013. Electra said of her ex-boyfriend Simon Cowell that he is “awesome and very charming.”
Simon Cowell and Carmen Electra
When it was revealed that Cowell had not remained faithful and was the reason for their breakup, he was not so awesome. “I just thought Simon was so much fun and was so smart and he’s really interesting,” Carmen stated.
Christina Applegate and Brad Pitt
When Christina Applegate, star of Married… With Children, brought Brad Pitt as her date to the 1989 MTV Video Music Awards, everyone assumed the two were dating. We can’t blame Christina for falling for Brad Pitt, who has since become one of the most attractive men on the planet.
Christina Applegate and Brad Pitt
Nevertheless, the blonde bombshell dumped her up-and-coming actor date for another man halfway through the night! Sebastian Bach, a Skid Row rocker, claims to be the guy, though Christina has never confirmed.
Jake Gyllenhaal and Kirsten Dunst
Kirsten Dunst was the “It Girl” of the moment after her role in the hit film Spiderman in 2002. As a result, it’s no surprise that heartthrob Jake Gyllenhaal had his sights set on the actress.
Jake Gyllenhaal and Kirsten Dunst
The famous actors married in 2002 and divorced two years later in 2004. While their hearts broke during this time, so did the hearts of all their fans when the split was announced. Dunst told Allure in 2009, “It would be nice to see him, but we’re not good friends.”
Ashton Kutcher and January Jones
It’s difficult to forget that Ashton Kutcher was famously married to actress Demi Moore, and that he is now married to Mila Kunis, a former co-star. Do you recall when Kutcher was dating January Jones, the star of Man Men? Let us refresh your memory in case you forgot.
Ashton Kutcher and January Jones
Before both of his high-profile relationships, the famous actor dated the blonde bombshell for three years, ending their relationship in 2001. Jones began dating Josh Groban two years later and dated him for the next three years.
Sheryl Crow and Owen Wilson
Sheryl Crow is best known for her engagement to Lance Armstrong, but she dated Owen Wilson from 1999 to 2001. She said, “I have always gone out with guys who were highly successful, which would seem like it would put me at an equal level.”
Sheryl Crow and Owen Wilson
She continued, “But what ends up happening is that one of you becomes smaller – and it was always me. I do think that sometimes in order for one person’s light to shine, everyone else has to dim theirs.”
Jessica Biel and Chris Evans
Jessica Biel is well-known for her marriage to Justin Timberlake, with whom she has a son. Biel, like her famous singer husband, had a number of high-profile and long-term relationships prior to marrying him.
Jessica Biel and Chris Evans
The Sinner star began dating fellow actor Chris Evans during her final years on 7th Heaven. The couple started dating in 2001 and dated on and off until June 2006. Biel met Timberlake after her relationship fell apart, and the rest is history!
Pink and Joey Fatone
Although they were not in a high-profile relationship, no one can deny that Pink dated a member of N’SYNC back in the early 2000s. Any girl would have been lucky to be on the arm of one of the guys when N’SYNC was the biggest boy band in the world.
Pink and Joey Fatone
She basically told Glamour, “He took me to Friendly’s on a date and he bought me an ice cream.” She went on, “Such a sweetheart. He asked my dad’s permission!”
Mariah Carey and Luis Miguel
In a recent interview with Cosmopolitan magazine, Mariah Carey discussed the men in her life, saying, “I haven’t had that many, but there has been a variety pack. I’ve only been with five people in my life, so I’m kind of a prude, honestly, compared to most others in the field.”
Mariah Carey and Luis Miguel
That gives each relationship she’s had a lot more weight, not the least of which was her relationship with Luis Miguel, the Latin crooner she dated from 1998 to 2001.
Nick Lachey and Kim Kardashian
Despite the fact that the 90s heartthrob and former member of boyband 98 Degrees only dated Kardashian for a short time, we consider it a success. “To say that she’s my ex is a little bit of a liberal use of the term.”
Nick Lachey and Kim Kardashian
When Kim got up to use the restroom halfway through the movie, Nick was astounded to see 25 paparazzi standing outside. Nick only had good things to say about the reality star, despite their brief dating history.
George Clooney and Lucy Liu
George Clooney was once regarded as one of Hollywood’s most eligible bachelors, even before his now-wife Amal showed up. He dated a slew of stunning and well-known actresses, including Lucy Liu from Charlie’s Angels.
George Clooney and Lucy Liu
Even though it was never confirmed, the couple was frequently seen together around the year 2000. The rumors were almost confirmed when paparazzi caught the two kissing in the back of a limousine in true Hollywood couple style on New Year’s Eve.
Matthew McConaughey and Janet Jackson
During a game of “Plead the Fifth” on the late-night talk show Watch What Happens Live, host Andy Cohen attempted to clear the air on the long-running rumor that McConaughey dated Janet Jackson.
Matthew McConaughey and Janet Jackson
McConaughey’s initial response was to laugh and try to avoid the question, but when Cohen persisted, he finally admitted that he had dated the singer… but only for a short time. He said, “We went and had dinner. That was sort of it.”
Brooke Shields and Nicolas Cage
Brooke Shields was once regarded as one of Hollywood’s most divisive “it” girls in the 1980s. So it’s no surprise that she’d hook up with Nicolas Cage, a bad boy who has a history of dating some of Hollywood’s most beautiful women (and ending each relationship disastrously).
Brooke Shields and Nicolas Cage
The specifics of their courtship are unknown, but when Cage invited Shields to the premiere of his film Moonstruck, it became clear that it was more than a whirlwind romance.
Julia Roberts and Liam Neeson
Although we love seeing our favorite A-List celebrities grace our screens, we are even more interested in finding out who they are dating, if not marrying! Even better when they’re dating.
Julia Roberts and Liam Neeson
However, it’s all too easy to forget about celebrities who dated a long time ago. Julia Roberts and Liam Neeson were once dating, and they are two of Hollywood’s biggest stars. After meeting on the set of the film Satisfaction, the two dated from 1988 to 1990 before marrying their respective partners.
Rachel McAdams and Michael Sheen
Rachel McAdams, the star of the romantic drama The Notebook, fell in love with British actor Michael Sheen on set. While filming Woody Allen’s Midnight in Paris, the two famous actors met. In 2013, the couple called it quits after three years of dating.
Rachel McAdams and Michael Sheen
Sheen always complimented his girlfriend, describing her as beautiful and hilarious. According to the actress, “Michael and I never spend more than three weeks apart — we rack up a lot of air miles — but you have to be quite adaptable in this business whether you are in a relationship or not.”
Zachary Quinto and Jonathan Groff
When Zachary Quinto met Jonathan Groff, he had just broken up with his long-term partner. Quinto met his soulmate, Jonathan Groff, the star of Mindhunter, after a string of misfortunes. Quinto once said of their relationship, “I’m incredibly happy, I’m incredibly lucky.”
Zachary Quinto and Jonathan Groff
Quinto spoke to Out Magazine in 2012 about his previous relationships, “I found myself in a pattern of being attracted to people who were somehow unavailable, and what I realized was that I was protecting myself because I equated the idea of connection and love with trauma and death.” Unfortunately, Groff and Quinto ended their relationship in July 2013 due to long-distance issues.
Cindy Crawford and Richard Gere
When they first met in 1988, Gere was a 39-year-old actor known for his role in Pretty Woman, and Crawford was a 22-year-old runway model. Crawford and Gere met at a backyard BBQ party hosted by a mutual friend. Despite their age difference, the lovers decided to marry in the Sin City chapel in Las Vegas a few years later, in 1991.
Cindy Crawford and Richard Gere
They divorced, however, only four years later, in 1995. Later, Crawford stated, “I think I was more willing at 22 to be, like, ‘Okay, I’ll follow,’ but then you start going, ‘Well, I don’t want to just follow—I want to lead sometimes and I want to walk side by side sometimes.’”
Anjelica Huston and Jack Nicholson
The Oscar-winning actress left her modeling career in New York in 1973 to return to her hometown of Los Angeles. Huston was only 21 years old when she met and fell in love with Nicholson, who was 14 years older than her, at his birthday party. The couple had been together for over two decades when he announced in 1989 that he was expecting a child with another woman, Rebecca Broussard.
Anjelica Huston and Jack Nicholson
In her memoir `Watch Me: A Memoir, Huston wrote, “Paternally, he would call us ‘my people.’ At the time, the generality of it bugged me; I wanted to be special, and I felt a loss of identity. ‘Where are my people?’ But there was very much a sense with Jack that one was on his team. And it was a good team to be on. A strong team.”
Tyra Banks and Drake
Drake, whose real name is Aubrey Graham, has a long history of failed relationships and ex-partners, including Tyra Banks. However, there was never a serious relationship between the supermodel and the famous Hollywood singer. Even though they only had one date together, it counts!
Tyra Banks and Drake
Drake said on The Ellen Degeneres Show: “It was just one date. We went to Disneyland in disguise actually, which was really fun. I don’t even know if it was like a date. It was like a get-together. We’re still really close.” Despite the fact that they only had one date together, the two remain close friends.
Jennifer Aniston and Paul Rudd
Aniston and Rudd have been together since they both starred in The Object of My Affection in 1998. Specifically, they fell in love and had a short-lived romance while filming the movie. They were, however, nothing more than very good friends in the end.
Jennifer Aniston and Paul Rudd
Throughout the years, Aniston and Rudd collaborated on a number of TV shows and films. When asked if it was strange to kiss her best friends on set in a GQ interview, Aniston simply replied, “Nah. I’ve kissed him for years.” Rudd later added, “We’ve made out for decades.”
Justin Timberlake and Fergie
Fergie dated Justin Timberlake before marrying Josh Duhamel, the father of her child and now ex-husband. After working together on the song “Where Is Love?” the two singers began dating. Fergie described the relationship as a “casual fling” in a 2003 interview with Cosmopolitan.
Justin Timberlake and Fergie
According to Fergie, “One of my good friends was dating J.C. Chasez, and so we’d all hang out with ‘NSync. Justin and I would go out together and have fun and make out. We went to Hawaii together, but we were never serious. He was Mr. Right Now.”
Luke Wilson and Gwyneth Paltrow
An on-set romance is a hit with everyone! Gwyneth Paltrow, an Oscar winner, dated Luke Wilson for a year after meeting during the filming of The Royal Tenenbaums. Paltrow described her ideal man in a Harper’s Bazaar interview from 2001, when they were allegedly dating, “He’s tall and thin, but muscular, to start with the superficial. A gentleman.”
Luke Wilson and Gwyneth Paltrow
She added, “Someone who’s well educated, funny, witty, artistic, and has a lot of integrity. He doesn’t have to grab all the attention in the room. A good kisser.” The actress, on the other hand, recently married Brad Falchuk, a well-known director and producer.
Madonna and Michael Jackson
When the Material Girl and the King of Pop attended the Academy Awards together in 1991, they stunned their fans. The public and the media mistook the relationship for a stunt for Madonna’s documentary Truth or Dare.
Madonna and Michael Jackson
These lovers undoubtedly had a good time at the after-parties and dinner dates they shared. Madonna recently addressed the rumors by posting an Instagram throwback photo. After Madonna publicly chastised Jackson’s appearance on television, they called it off.
Miley Cyrus and Nick Jones
In 2006, the Disney Channel premiered the biggest teen romance of all time, but it only lasted a year. Despite the fact that Nick Jones is now happily married to Priyanka Chopra, he and Miley were once madly in love. Cyrus said for Seventeen, “At first I bawled for a month straight. And I dyed my hair black. When we were dating, Nick wanted me to get highlights—and so I did that, and I got myself looking great.”
Miley Cyrus and Nick Jones
She added, explaining her struggles after the breakup, “And then, on the day we broke up, I was like, I want to make my hair black now—I don’t want to look pretty; I want to look hard-core. I was rebelling against everything Nick wanted me to be. And then I was like, I’ve got to be by myself for now, and just figure out who I really am.”
Courtney Love and Edward Norton
If we’re being honest, Courtney Love and Edward Norton are probably the most surprising pairing on this list. Love’s then-husband, Kurt Cobain of Nirvana, had both passed away by 1996.
Courtney Love and Edward Norton
When Love began dating co-star Norton, she had just received a Golden Globe nomination for her performance in The People vs. Larry Flynt. They dated until 1999, and were even engaged for six months, before calling it quits after five years together.
Busy Philipps and Colin Hanks
Busy Philipps attended Loyola Marymount University, where she met Colin Hanks, son of the legendary Tom Hanks, before landing her big break on the teen comedy Freaks and Geeks. This was, of course, prior to Colin’s first television appearance on the science fiction drama Roswell.
Busy Philipps and Colin Hanks
Philipps and Hanks dated for the majority of the 1990s before calling it quits. Their romantic love faded, but their friendship endured. In fact, the two of them are still very close and even go on vacations with their spouses together.
Jennifer Love Hewitt and Will Friedle
Jennifer Love Hewitt was a hot commodity in the 1990s, starring in films like I Know What You Did Last Summer and Can’t Hardly Wait, as well as Trojan War, where she eventually met Will Friedle — does the name sound familiar?
Jennifer Love Hewitt and Will Friedle
That’s probably because you remember him from the hit show Boy Meets World!, where he played big brother Eric Matthews. Regardless, Hewitt and Friedle hit it off and began dating while filming the film in 1997, despite having met previously. This fling would, however, be short-lived, and each of them would go on to marry someone else.
Zooey Deschanel and Jason Schwartzman
When Zooey Deschanel began dating actor Jason Schwartzman in 2003, she had already made her film debut in the 1999 comedy-drama Mumford and landed a supporting role in Cameron Crowe’s 2000 film Almost Famous.
Zooey Deschanel and Jason Schwartzman
Schwartzman, who is known for his frequent collaborations with Wes Anderson, had already starred in the 1998 hit film Rushmore when the two began dating. Although Deschanel and Schwartzman aren’t an out-of-the-ordinary couple, their two-year relationship was kept under wraps until their split in October 2005.
Katie Holmes and Chris Klein
Katie Holmes was in a relationship with American Pie actor Chris Klein before she began dating now-ex-husband Tom Cruise in April of 2005. When Holmes met and began dating Klein in 2000, she had already achieved fame as Joey Potter on the teen drama television series Dawson’s Creek (1998-2003).
Katie Holmes and Chris Klein
They dated for five years and were engaged during that time before breaking up in early 2005. Even so, they have managed to stay friends over the years since their breakup.
Edward Norton and Salma Hayek
Salma Hayek is rumored to be married to Francois-Henri Pinault, a French businessman. People forget, however, that she once dated fellow actor Edward Norton. Hayek had a relationship with the American History X star at the end of the 1990s and the beginning of the 2000s.
Edward Norton and Salma Hayek
Funny story: it turns out they were both treated by the same chiropractor, which is how they met! Despite this, they split up in 2003, and Hayek is now with Pinault.
Shia LaBeouf and Hilary Duff
Shia LaBeouf’s career has been a rollercoaster ride to say the least. The eccentric actor appears to have returned to a rich vein of form in recent times, despite many highs and lows.
Shia LaBeouf and Hilary Duff
Casual fans may have forgotten about his brief romance with Hilary Duff, of all people. Their first date, according to LaBeouf in an interview with Hollywood Life, was “probably the worst date either of us have ever had.”
Josh Hutcherson and Vanessa Hudgens
Vanessa Hudgens appeared to be in a vulnerable state following her breakup with High School Musical co-star Zac Efron. Hudgens is said to have started dating Josh Hutcherson, with whom she was working on Journey 2: The Mysterious Island, shortly after.
Josh Hutcherson and Vanessa Hudgens
Hutcherson eventually revealed that they had broken up. “We were at one point, but she broke my heart,” he jokingly said. “I’m just kidding. That was a while ago, we’re just really good friends now.”
David Arquette and Drew Barrymore
Even though the fact that David Arquette and Drew Barrymore reportedly had a brief romance isn’t surprising, it is something that many fans are unaware of. Despite the fact that Barrymore has previously vehemently denied such claims, Arquette begs to differ.
David Arquette and Drew Barrymore
He initially claimed that they began dating before actually working together on Never Been Kissed. Arquette said on PeopleTV’s Couch Surfing, “We also dated, but she denied it on Howard Stern.”
Joaquin Phoenix and Liv Tyler
Joaquin Phoenix has risen from the ashes of his bizarre acting hiatus to reclaim his place as one of Hollywood’s most sought-after actors. Liv Tyler recalls dating the Joker star when they were both in their 20s.
Joaquin Phoenix and Liv Tyler
Tyler told Elle, “I’m friends with all my exes! I love them so much! I guess it depends on what happens, right? I consider Joaquin and all of his sisters to be like family.”
Matt Damon and Winona Ryder
He’s known for roles in films like Good Will Hunting and The Bourne Identity, and she’s recently become a household name thanks to her role in Stranger Things, but Matt Damon and Winona Ryder dated before all of this.
Matt Damon and Winona Ryder
In fact, the famous couple dated for two years before ending their relationship in March 2000. However, not all hope was lost, as Damon married Luciana Barroso five years later, and Ryder married Scott Mackinlay Hahn in 2011.
Tom Cruise and Penelope Cruz
Tom Cruise has been married three times, with two of those marriages being very public. Cruise met Penelope Cruz, a fellow actress, after his second marriage to Nicole Kidman ended in divorce.
Tom Cruise and Penelope Cruz
In 2000, the two met on the set of Vanilla Sky and remained together for three years before calling it quits in January 2004. Cruise married Katie Holmes, whom he later divorced, two years later, and Cruz married Javier Bardem in 2010.
Cameron Diaz and Justin Timberlake
Cameron Diaz is a well-known actress around the world, but prior to marrying her current husband, Benji Madden, in 2015, it seemed that her love life was not going well.
Cameron Diaz and Justin Timberlake
In fact, the What Happens In Vegas star has had long-term relationships with actors Jared Leto and Alex Rodriguez, but can you recall when Cameron was dating Justin Timberlake? The actress met the singer in April 2003 and dated him until January 2007, despite the fact that she was eight years older than her.
Jennifer Garner and Scott Foley
When the media speculated that Jennifer Garner and her ex-husband, Ben Affleck, were divorcing, they made headlines for months. The couple confirmed their shocking divorce, putting an end to the rumors, but it was not the first for the 13 Going On 30 star.
Jennifer Garner and Scott Foley
Her divorce from her then-husband, Scott Foley, was finalized a year before she married Affleck. The couple met on the set of Felicity, but Garner told Allure, “We didn’t have a shot. He’s a really good guy, and we just imploded.”
Wilmer Valderrama and Lindsay Lohan
It’s difficult to keep up with Lindsay Lohan’s antics, but it’s worth remembering that the former child star dated Wilmer Valderrama from That ’70s Show. Wilmer went on to have a long-term relationship with Demi Lovato, which sparked enough controversy in and of itself, so they may be forgotten.
Wilmer Valderrama and Lindsay Lohan
Even so, on Lohan’s 18th birthday in July 2004, the secret of Lohan and Valderrama’s relationship was revealed. However, it was not to last, and they filed for divorce later that year.
Gwyneth Paltrow and Brad Pitt
Gwyneth Paltrow and Brad Pitt may have had high-profile marriages and subsequent divorces, but they were once Gwyneth Paltrow and Brad Pitt. Paltrow and Pitt co-starred in the 1995 film Se7en before they met Chris Martin, Jennifer Aniston, or Angelina Jolie.
Gwyneth Paltrow and Brad Pitt
The pair were engaged at one point in their relationship, but the engagement was called off later. Paltrow told Howard Stern in an interview, “I wasn’t ready, and he was too good for me.”
Alexis Bledel and Milo Ventimiglia
When Gilmore Girls was still on the air, fans had the opportunity to see Alexis Bledel and Milo Ventimiglia interact on screen. Meanwhile, since 2003, the actor and actress have been dating off-screen.
Alexis Bledel and Milo Ventimiglia
That’s right, the couple brought their Gilmore Girls romance to life, much to the delight of fans of the show. While the co-stars made a lovely couple, their relationship only lasted three years, and they split up in 2006.
Kid Rock and Pamela Anderson
Kid Rock and Pamela Anderson have made headlines over the years for a variety of reasons, not all of which are positive. Their engagement made headlines in 2003, and they broke up before walking down the aisle again in 2004.
Kid Rock and Pamela Anderson
Unlike most couples who call off their engagement and go their separate ways, Anderson and Kid Rock famously married on a yacht in 2006. While fans thought this was the real deal, Anderson filed for divorce four months later.