For most celebrities, they want to be famous for their talent, but in many cases, it all depends on who you are dating and when. When two huge stars get together, the media is sent into a frenzy. The world waits for every sighting and photo of the pair. However, the “Hollywood Curse” means relationships in the City of Dreams are not to last. But if these celebrities really think we are going to forget about their past romances, then they are mistaken. We are now going to refresh your memory with some of the most famous celebrity relationships from the past that you may have forgotten existed.
Nicole Kidman and Lenny Kravitz
Nicole Kidman is known to pack on the PDA with her singer husband, Keith Urban. However, before Keith, and even Tom Cruise for that matter, Kidman was once engaged to musician Lenny Kravitz.
While the former couple was engaged in 2003, the Stepford Wives star went on to explain that she “wasn’t ready” to get married, so the pair never did. However, Nicole Kidman has since gone on to star alongside Kravitz’s daughter, Zoe, in the hit series, Big Little Lies.
Sandra Bullock and Matthew McConaughey
After starring alongside one another in A Time to Kill, Sandra Bullock and Matthew McConaughey started dating. It’s hard to remember a time before McConaughey was married to Camilla Alves, with the pair being envied for their beautiful romance, as well as their beautiful looks.
However, four years before tying the knot, McConaughey spoke of his romance with Bullock to Playboy stating, “She’s not a little girl. She’s a woman.” He continued to speak highly of his then-beau expressing, “She could run a country.”
Ryan Reynolds and Alanis Morissette
Ryan Reynolds and his current wife, Blake Lively, have proven they are “couple goals” on their respective social media pages. However, before meeting the Gossip Girl star, marrying her, and having two children, the Deadpool actor dated Alanis Morissette.
The Canadian actor and the Canadian singer met in 2002 and continued to date for the next four years. In fact, Reynolds had proposed to the “Ironic” singer, but the couple never said their “I do’s.” Rather, they parted ways in 2006.
Reese Witherspoon and Jake Gyllenhaal
It was a sad time for Reese Witherspoon when her marriage to the father of her kids, Ryan Philippe, broke down. However, fans rejoiced when it was reported that Witherspoon began dating the very handsome Jake Gyllenhaal.
The two megastars met while on the set of the movie Rendition in 2007, and sparks began to fly. They officially became a couple soon after but, it was only to last two years since the Big Little Lies star and the Brokeback Mountain actor ended in 2009.
Mila Kunis and Macaulay Culkin
While starring on That ’70s Show, Mila Kunis was dating Home Alone star, Macaulay Culkin. The couple began dating in 2002 and were a couple for the next eight years.
Speaking to Howard Stern, Kunis recalled, “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!” It seems the attraction between the pair was no longer there, however, since they called it quits in 2011.
Leonardo DiCaprio and Gisele Bündchen
He is one of the world’s most famous bachelors, and we still wait to see which woman manages to sweep Leonardo DiCaprio off his feet. It is hard to tell since he once dated the one-time highest-paid supermodel, Gisele Bundchen.
Before marrying top football star, Tom Brady, Gisele dated Leo on and off for almost six years. Although they made a beautiful couple, it was not to last. Perhaps Leo is pulling a George Clooney and will get married in his 50s.
Blake Lively and Penn Badgley
We may have mentioned that Ryan Reynolds and Blake Lively were total “couple goals” but, at one point in time, the world was rooting for Blake Lively and her co-star, Penn Badgley.
Not only were the two co-stars, but they were also each other’s love interest on Gossip Girl. Having gone from an on-screen relationship to an off-screen one, fans of Gossip Girl rejoiced at the news. After three years of dating, the pair called it quits in 2010 but, thankfully, they ended up together on Gossip Girl.
Bradley Cooper and Renée Zellweger
Bradley Cooper is on every girl’s radar but has officially been off the market since 2015. However, before meeting his current girlfriend and mother of his child, Irina Shayk, he was dating actress Renée Zellweger.
The pair met on the set of the 2006 thriller, Case 39, but began dating in 2009 when the film was released. After months of media speculation on the status of their relationship, the couple refused to ever speak about it, but would make appearances together. In 2011, the former couple called it quits.
Lindsay Lohan and Samantha Ronson
After her relationship with That ’70s Show star, Wilmer Valderrama, ended, Lindsay Lohan dated Hard Rock Cafe heir Harry Morton in 2006. Following their breakup, The Parent Trap star became linked to British DJ, Samantha Ronson.
The pair began dating in 2008, but the high-profile relationship ended between the actress and the musician in 2009. Speaking of her relationship, Lohan told Us Weekly that their romance was not to last because “Two toxic people cannot be together. End of story.”
Angelina Jolie and Jonny Lee Miller
Angelina Jolie has certainly made her fair share of media headlines due to her relationship choices, not to mention her scandals and affairs in the process.
However, before her high profile marriage to her Mr & Mrs Smith co-star, Brad Pitt, Jolie was married to Jonny Lee Miller. Similarly to her and Pitt, the former couple met on the set of their film, Hackers, in 1995. They were married a year later in March 1996 but split up three years later in 1999.
Michael Keaton and Courtney Cox
She is best known for playing Monica Geller on the hit sitcom, Friends, but before becoming one of the most well-known and highest paid actresses for this role, Courtney Cox was in a relationship with Michael Keaton.
In fact, Keaton and Cox dated for over six years, before splitting up in 1995. This was just one year after she first appeared as a leading character on the NBC sitcom, and she later went to marry David Arquette. They share one child together but have since divorced.
Sarah Jessica Parker and Robert Downey Jr.
Sarah Jessica Parker has nothing but beautiful words to say about her current husband, Matthew Broderick, but she did have another serious relationship before meeting her soulmate.
In fact, the Sex and the City star dated fellow actor Robert Downey Jr. before they split up in 1991. The pair were together for seven years before putting an end to their relationship, and the reason for the breakdown of their relationship was the actor’s struggles with addiction at the time.
Kim Kardashian and Nick Cannon
Kim Kardashian is now famously married to rapper and singer Kanye West, with the world watching her and her family’s every move. However, before we were all Keeping Up with the Kardashians, Kim was trying to keep up with Nick Cannon.
The pair began dating in September 2006 before Kim Kardashian was one of the most famous women alive, but it was only to last four months. The pair called it quits in January 2007 and Cannon later went on to marry, and divorce, Mariah Carey.
Michelle Rodriguez and Zac Efron
When it was reported that Michelle Rodriguez and Zac Efron were an item, everyone labeled them to be an unlikely pair. With Rodriquez being ten years older than the High School Musical star, not many people saw this relationship coming.
They proved everyone right since they dated for just two months before a “very mutual” split. Perhaps the fact that Rodriguez got into a relationship with model Cara Delevingne that same year had something to do with it.
Orlando Bloom and Kate Bosworth
Orlando Bloom is another actor most girls swoon over whenever he comes on screen, but some lucky ladies have had the opportunity to date the Pirates of the Caribbean star.
While he is most famous for being married to the beautiful Victoria’s Secret model, Miranda Kerr, in 2010, he was previously in a relationship with Kate Bosworth. The Blue Crush star dated the handsome actor for two years before ending it in 2005. Kate, however, is just more proof that Orlando dates beautiful ladies.
Ben Affleck and Gwyneth Paltrow
Before marrying a successful British singer, it seems that Gwyneth Paltrow was into leading Hollywood men. While things didn’t work out with Brad Pitt, she also dated Good Will Hunting actor, Ben Affleck.
The famous pair began dating in 1997 for two years until 1999, before getting back together briefly and ending things for good 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
Mark Ronson is famous for producing hits such as “Uptown Funk” by Bruno Mars and “Valerie” by Amy Winehouse, so it is no surprise Rashida Jones was once attracted to such a talented star.
Ronson and Jones dated from 2002 to 2004 and were even engaged at one point. Ronson proposed to the actress after one year together, by creating a crossword puzzle with the message “Will you marry me.” Their engagement lasted one 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 during the early 2000s thanks to their respective singing careers, but they became a power duo when they became romantically linked.
The singers began dating in 2001, and Rozonda even starred in Usher’s video for his single “U Got It Bad” that same year. However, the pair were reported to have broken up in 2003 because of Usher’s infidelity, although the TLC singer said, “We broke up because I guess it was that time or whatever.”
Justin Timberlake and Jenna Dewan-Tatum
She may have been in one of Hollywood’s favorite marriages before parting ways with her husband of ten years, Channing Tatum, but before she even met her former husband, Jenna Dewan was linked to Justin Timberlake.
Back in 2002, Jenna was a backup dancer for the “Cry Me a River” singer, and it was also around the same time that Timberlake’s relationship with Britney Spears ended. “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 may be the first time you’re seeing Brad Pitt on this list, but it definitely isn’t the last time. Then again, that’s not much of a surprise considering the ‘ladies man’ reputation he’s managed to build over the years.
In any case, here he is with Shalane McCall — a (now) former child actress and model best known for her portrayal as Charlotte “Charlie” Wade on the CBS prime-time soap opera Dallas. In 1987, when Pitt was 24 years old, he landed a four-episode stint on Dallas where he met 15-year-old McCall and began an eyebrow-raising relationship with her.
Seal and Tyra Banks
Many people are most likely to remember Seal’s high-profile marriage to model Heidi Klum. However, before the singer even met the German beauty, he dated another top supermodel.
It seems Seal had a thing for models since he briefly dated Tyra Banks in 1996. While Tyra Banks has not proven to be so lucky in love since their brief romance, Seal went on to marry Heidi Klum in 2005, and their marriage lasted nine years before their divorce was finalized in 2014.
Scarlett Johansson and Jack Antonoff
Before Jack Antonoff began dating Girls actress, Lena Dunham, he dated Scarlett Johanson. In fact, the two actors dated for two years when they were 17 and in high school.
Moreover, the teenage sweethearts attended prom together in 2002. Things are very different these days for the exes and, while Antonoff’s relationship with Lena recently came to an end, Scarlett has been married, and divorced, twice. She divorced Ryan Reynolds in 2011 and, just last year, her and Romain Dauriac divorced after three years of marriage.
Aubrey Plaza and Michael Cera
Funnyman Michael Cera started dating his Scott Pilgrim vs. the World co-star, Aubrey Plaza, in 2010. The actors dated for over a year before calling it quits, but Plaza later spoke to Vulture about their romance.
“We drove across the country after we shot that movie and almost got married in Vegas,” she recalled. A year later, Aubrey began dating Jeff Baena, and the couple has been together ever since, so it doesn’t look like Michael Cera will ever be back in the picture.
Ryan Gosling and Sandra Bullock
In 2011 it was rumored that Sandra Bullock could be dating Ryan Reynolds, but this would not have been the first Ryan in her life. In fact, the Miss Congeniality actress dated fellow actor Ryan Gosling for one year in 2002.
The couple made headlines when their romance went public after meeting on the movie Murder By Numbers, and not just because they were both big names in Hollywood. Rather, it was their 16-year age difference that caught the attention of the media.
Madonna and Dennis Rodman
Madonna had a very high-profile relationship with director Guy Ritchie, and an even more public divorce when their marriage came to an end in 2008. But before Ritchie, there was Dennis Rodman.
The “Papa Don’t Preach” songstress dated the basketball player for a brief time in 1994. This came after his divorce from Annie Bakes, and the retired basketball player has since gone on to marry, and divorce, twice more.
Cameron Diaz and Jared Leto
Actress Cameron Diaz dated the 30 Seconds To Mars frontman, Jared Leto, from 1999 to 2003. In fact, it was rumored that the former couple was even engaged during this time, with Diaz reportedly wearing a $15,000 engagement ring to the Golden Globes in 2003.
It seems that the couple was heading in the other direction that same year, however, and have continued to go their separate ways. Diaz has had a string of relationships before settling down with Benji Madden, and Leto remains unmarried.
Kate Hudson and Alex Rodriguez
Alex Rodriguez has been linked to Cameron Diaz and Madonna and has been dating Jennifer Lopez since 2007. However, there was a time when the baseball star dated How to Lose a Guy in 10 Days actress, Kate Hudson.
The famous duo dated for seven months in 2009, before calling it quits in 2009. This was just a year after his divorce from his wife of six years, Cynthia Scurtis, was finalized. A-Rod and Cynthia welcomed two daughters together during their marriage.
Lamar Odom and Taraji P. Henson
It is hard to remember who else Lamar Odom was romantically linked to other than his high-profile relationship with Khloe Kardashian. While that marriage was not to last, it remains to be one that makes many media headlines due to the unfortunate actions of the basketball player.
However, Odom was once linked to actress Taraji P. Henson, and she even took him to a Golden Globes party in 2009. It was rumored that Odom had proposed to Henson in 2009, just weeks before popping the question to Khloe.
Wilmer Valderrama and Mandy Moore
Wilmer Valderrama has had several high-profile relationships including one with Lindsay Lohan and, more recently, with songstress Demi Lovato. However, between 2001 and 2002, the That ’70s Show actor dated the This Is Us actress and singer, Mandy Moore.
In fact, Moore then went onto date Scrubs actor, Zach Braff, in 2004, before settling down with her partner, Ryan Adams, in 2009. The pair has since divorced, and Wilmer remains unmarried.
Tom Cruise and Cher
Perhaps Cher wishes she could turn back time after revealing to Andy Cohen that Top Gun actor, Tom Cruise, was in her “top 5.” The pair only briefly dated, meanwhile, in 1985, and didn’t go further than a fling so many people may not even remember the former couple.
Rather, Cher’s marriage to Sonny Bono during the 70s was better known, and Cruise’s relationships and marriages to Nicole Kidman and Katie Holmes were more high-profile than his past with the singer.
Nick Jonas and Selena Gomez
It’s hard to try and keep up with who Selena Gomez is dating these days – is it Justin Bieber, is it The Weeknd, is it Justin Bieber again? Meanwhile, before romances between the former Disney child star and either of the singers began, Gomez dated fellow Disney actor and boyband member, Nick Jonas.
During this time, the Jonas Brothers released their single “Burnin Up” which became their first top five hit in the United States, and Gomez appeared in the song’s music video.
Alyssa Milano and Justin Timberlake
While Jenna Dewan-Tatum emphasized that she was not the rebound for Mr. Timberlake following his devastating break-up with Britney Spears, Alyssa Milano claims she was.
It was years later that the Charmed actress confirmed she briefly dated Justin Timberlake back in the early 2000s and confessed, “Right after Britney broke his heart, I swooped in for the kill!” The pair failed to have a serious relationship, and Justin Timberlake went on to have a long-term relationship with Cameron Diaz before eventually marrying Jessica Biel.
David Spade and Julie Bowen
David Spade was described by E! News as “a bachelor-era George Clooney of the comedy world,” and there is a great reason for this description.
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 is still yet to settle down with any. Amongst this list of women is Modern Family actress, Julie Bowen. The pair dated for a year back in 2002 when Spade starred on Just Shoot Me! and Bowen on Ed.
Rosario Dawson and Danny Boyle
Back in 2013, Rosario Dawson and Danny Boyle were spotted looking more than friends on several occasions. However, when rumors swirled that the alleged couple had broken up, Rosario spoke to NET-A-PORTER about the breakup.
She told the publication: “It’s not like we announced our relationship, so it’s not like we’re going to announce our breakup.” Meanwhile, the pictures did all the talking, with the director and actress spending time with just one another and looking closer than just friends.
Jamie Dornan and Keira Knightley
He now has the lucrative role of playing Mr. Christian Grey on screen, but before he was cast to star in the film adaptation of the hit book, he had caught the eye of British actress Keira Knightley.
The beautiful pair began dating in 2003 after they met shooting an ad campaign but went their separate ways in 2005. During this time, both actors were pretty lowkey actors, but have since gone on to achieve worldwide stardom with Keira starring in the hit Pirates of the Carribean franchise.
50 Cent and Chelsea Handler
Perhaps one of the most unexpected pairings on this list is 50 Cent and Chelsea Handler. The comedic talk-show host dated the famous rapper back in 2010, even though she stated in an Oprah interview “I’m not gonna date somebody whose name is a number.”
Nevertheless, it seems this man, whose stage name is a number, swept the blonde beauty off her feet, and she found herself “satiated” during their time together. Any romance between the two, however, was not to last.
Seth MacFarlane and Emilia Clarke
He is the mastermind behind the hit animated sitcom Family Guy and she plays Khaleesi, Mother of Dragons, in HBO’s Game of Thrones, and in 2012 Seth MacFarlane and Emilia Clarke’s paths somehow crossed.
However, after just six months of dating, the unexpected pair called it quits in 2013. Meanwhile, a year later, Clarke was voted the most desirable woman in the world by AskMen readers, and Esquire’s Sexiest Woman Alive in 2015, so it seems Seth missed out big time.
Scarlett Johansson and Sean Penn
In 2011, Scarlett Johansson and Sean Penn made headlines when their relationship became public. Their romance caused an outcry due to their massive age difference, with Penn being 50-years-old at the time, and the Lost in Translation actress just 26.
However, after five months together, reports swirled that Sean Penn “did not want to be tied down” to Scarlett and, therefore, called off their romance. Further reports suggested that Johansson was eager to rekindle the flame between the two, but was not successful.
Simon Cowell and Carmen Electra
For a brief time in December 2012 to the following February, music mogul Simon Cowell dated former Playboy model, Carmen Electra. Speaking of her former beau, Electra said she thinks Simon Cowell is “awesome and very charming.”
However, he was not so awesome when it was reported that Cowell had not remained faithful and was the cause of their split. Nevertheless, Carmen did state, “I just thought Simon was so much fun and was so smart and he’s really interesting.”
Christina Applegate and Brad Pitt
When Married… With Children star, Christina Applegate brought Brad Pitt as her date to the 1989 MTV Video Music Awards, everyone rightfully believed the pair were dating.
With Brad Pitt being considered one of the most attractive men in the world since then, we can’t blame Christina for falling for him. However, halfway through the night, the blonde bombshell ditched her up-and-coming-actor date for another man! Skid Row rocker Sebastian Bach insists that he was the guy, although Christina has never confirmed.
Jake Gyllenhaal and Kirsten Dunst
Following her feature in the hit film, Spiderman, in 2002, Kirsten Dunst was the “It Girl” of the moment. It is no surprise, therefore, that heartthrob Jake Gyllenhaal had his eyes set on the star.
The famous actors became a couple in 2002 before splitting two years later in 2004. While their hearts may have been breaking during this time, so were all their fans’ when the split was announced. “It would be nice to see him, but we’re not good friends,” Dunst told Allure in 2009.
Ashton Kutcher and January Jones
It is hard to forget the time Ashton Kutcher was famously married to actress Demi Moore, and even the fact that he is now married to his former co-star, Mila Kunis.
However, do you remember when Kutcher was dating Man Men star, January Jones? Just in case you forgot, let us refresh your memory. The famous actor dated the blonde bombshell from 1998 for three years, before both of his high-profile relationships, and before calling it quits in 2001. Two years later, Jones began dating Josh Groban for the next three years.
Sheryl Crow and Owen Wilson
Sheryl Crow was famously engaged to Lance Armstrong, but before Lance, there was Owen Wilson, who she dated from 1999 until 2001. “I have always gone out with guys who were highly successful, which would seem like it would put me at an equal level,” she says.
“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 famously married to Justin Timberlake, and the couple has welcomed a son together. However, just as her famous singer husband had several high-profile and long-term relationships before tying the knot, so did Biel.
During her final years on 7th Heaven, The Sinner star began dating fellow actor, Chris Evans. The couple began their relationship in 2001 and continued to date on-and-off until June 2006. Following the breakdown of her relationship, Biel met Timberlake, and the rest is history!
Pink and Joey Fatone
They may not have been in a high-profile relationship, but no one can ignore the fact that Pink once dated a member of N’SYNC during the early 2000s. At a time when N’SYNC was the biggest boy band around, any girl would have been lucky to be on the arm of one of the guys.
“He took me to Friendly’s on a date and he bought me an ice cream,” she revealed to Glamour. “Such a sweetheart. He asked my dad’s permission!”
Mariah Carey and Luis Miguel
Mariah Carey recently opened up about the men in her life in an interview with Cosmopolitan magazine, 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,”
That gives each relationship she’s had quite a bit more significance, not in the least of which was Luis Miguel, the Latin crooner she dated from 1998-2001.
Nick Lachey and Kim Kardashian
The 90s heartthrob and former member of boyband 98 Degrees may have not dated Kardashian for long, but it still counts in our book. “To say that she’s my ex is a little bit of a liberal use of the term.”
The two went to see a movie at once point, and Nick was astounded when 25 paparazzi were standing outside when Kim got up to use the restroom halfway through the movie. Brief as their dating history is, Nick only had nice things to say about the reality star.
George Clooney and Lucy Liu
Before his now-wife Amal showed up, George Clooney was long considered one of Hollywood’s most eligible bachelors. He dated all manner of beautiful and famous actresses, including Charlies Angels actress Lucy Liu.
Although it was never confirmed, the pair grew were seen together numerous times around the year 2000. The rumors were all but confirmed when the two were snapped by paparazzi sharing a New Year’s smooch in the back of a limousine in true Hollywood couple style.
Matthew McConaughey and Janet Jackson
During a game of “Plead the Fifth” on the nighttime talk show Watch What Happens Live, host Andy Cohen sought to set the record straight on the longstanding rumor that McConaughey once dated Janet Jackson.
McConaughey’s response was to laugh and attempt to evade the question, but when Cohen pressed him, he finally answered that he had, in fact, dated the singer… but not for very long. “We went and had dinner. That was sort of it,” he said.
Brooke Shields and Nicolas Cage
Back in the ’80s, Brooke Shields was considered one of Hollywood’s most controversial “it” girls. So it’s no wonder that she would get together with bad boy Nicolas Cage, who has a history of dating some of Hollywood’s most beautiful women (and ending each relationship disastrously).
The extensive details of their courtship aren’t known, but when Cage brought Shields to the premiere of his film Moonstruck, people began to suspect it was more than just a fling.
Julia Roberts and Liam Neeson
While we love to watch some of our favorite A-List stars grace our screens, we love nothing more than knowing who they are dating, if not marrying! What’s even better, is when they are dating each other.
But sometimes, it’s easy to forget about celebrities who dated long ago. These are two of Hollywood’s biggest stars, and it’s true, Julia Roberts and Liam Neeson used to date. Before marrying their respective partners, the pair dated from 1988 to 1990 after they met on the set of the film, Satisfaction.
Rachel McAdams and Michael Sheen
The star of the romantic drama The Notebook, Rachel McAdams, fell in love with the British actor Michael Sheen on set. The two famous actors met while filming Woody Allen’s Midnight in Paris. After dating for three years, the lovebirds called it off in 2013.
Sheen talked nicely of his girlfriend, always calling her beautiful and endlessly funny. The actress said, “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
The Star Trek actor Zachary Quinto had just gotten out of a serious relationship when he met Jonathan Groff. After many misfortunate relationships, Quinto found his soulmate, the Mindhunter star, Jonathan Groff. “I’m incredibly happy, I’m incredibly lucky,” Quinto described their relationship back in the day.
In 2012, Quinto talked of his previous relationships for Out Magazine, “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 broke up in July of 2013, because of problems caused by long-distance.
Cindy Crawford and Richard Gere
Gere was a 39-year-old actor famous for his role in Pretty Woman, and Crawford was a 22-year-old runway model when they first met in 1988. Crawford and Gere met at a mutual friend’s backyard BBQ party. A few years later, in 1991, the lovers decided to marry in the Sin City chapel in Las Vegas, despite the age gap.
However, they divorced only four years later, in 1995. Crawford later said, “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
In 1973, the Oscar-winning actress left her modeling career in New York to move back home to Los Angeles. Huston was only 21 when she met the 14 years older Nicholson at his birthday party and fell in love. The relationship lasted for over two decades until 1989 when he announced that he was expecting a baby with another woman, Rebecca Broussard.
Huston wrote in her book Watch Me: A Memoir, “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, aka Aubrey Graham, has a lengthy list of failed relationships and ex-partners, including Tyra Banks. However, the supermodel and the famous Hollywood singer were never in a serious relationship. After all, they only went out on one date together, but it counts!
On The Ellen Degeneres Show, Drake said: “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.” Even though they shared only one date, the two are still very good friends.
Jennifer Aniston and Paul Rudd
Aniston and Rudd’s relationship dates way back to 1998 when they both starred in The Object of My Affection. Namely, during the filming of the movie, they fell for each other and had a short-lived romance. However, they ended up being nothing more than very good friends.
Aniston and Rudd filmed many TV shows and movies together during the years. In an interview for GQ, when asked if it was weird to kiss her best friends on the set, Aniston simply answered, “Nah. I’ve kissed him for years.” Rudd later added, “We’ve made out for decades.”
Justin Timberlake and Fergie
Fergie dated Justin Timberlake way before she settled down with the father of her child and now ex-husband, Josh Duhamel. After their collaboration on the song “Where Is Love?” the two singers started dating. In a 2003 interview for Cosmopolitan, Fergie described the relationship as nothing but a casual fling.
Fergie said, “One of my good friends was dating J.C. Chasez, and so we’d all hang out with ‘N Sync. 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
Everyone loves an on-set relationship! The Oscar-winning actress, Gwyneth Paltrow, dated Luke Wilson for a year after they connected during the filming of The Royal Tenenbaums. In a 2001 interview for Harper’s Bazaar, when they were allegedly dating, Paltrow described her perfect man, “He’s tall and thin, but muscular, to start with the superficial. A gentleman.”
“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,” she added. However, the actress has recently secretly married the famous director and producer, Brad Falchuk.
Madonna and Michael Jackson
The Material Girl and the King of Pop shocked their fans in 1991 when they attended the Academy Awards together. The public and media believed that the relationship was just a performance for Madonna’s documentary Truth or Dare.
There is no doubt that these lovers had fun during after-parties and dinner dates they attended together. Madonna addressed the rumors recently and posted a throwback picture on Instagram. They called it off after Madonna criticized Jackson’s look publicly on the TV.
Miley Cyrus and Nick Jones
The biggest teen romance on the Disney Channel started in 2006, but it ended only one year later. Even though Nick Jones is now happily married to Priyanka Chopra, Miley and himself were madly in love back in the day. “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,” Cyrus said for Seventeen.
“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,” she added, explaining her struggles after the breakup.
Courtney Love and Edward Norton
If we’re being honest, this might be the most unexpected duo on this list — Courtney Love and Edward Norton. It was 1996 and Love’s then-husband, as well as Nirvana’s leading man Kurt Cobain had since passed.
Love had just earned a Golden Globe nomination for her performance in The People vs. Larry Flynt when she began dating co-star Norton. The pair stayed together until 1999 and were even engaged for six months before calling it quits after five years.
Busy Philipps and Colin Hanks
Before Busy Philipps made her big break on the teen-comedy Freaks and Geeks, she attended Loyola Marymount University where she met Colin Hanks — son of the legendary Tom Hanks. This was, of course, also before Colin made his first television debut on the sci-fi drama Roswell.
In any event, Philipps and Hanks dated throughout the 1990s before calling it quits. Although their romantic love faded, their friendship didn’t. In fact, the two of them are still extremely close and even take vacations together with their spouses.
Jennifer Love Hewitt and Will Friedle
There’s no denying that actress Jennifer Love Hewitt was a hot commodity in the ’90s starring in films like I Know What You Did Last Summer and Can’t Hardly Wait, and Trojan War where she ultimately hit it off with Will Friedle — does the name sound familiar?
That’s probably because you used to watch him play big brother Eric Matthews on the hit series Boy Meets World! Anyway, Hewitt and Friedle hit it off and began dating while filming the movie in 1997, although they had been introduced before this. This fling wouldn’t last long, though, and each of them would go on to marry different people.
Zooey Deschanel and Jason Schwartzman
Zooey Deschanel 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 when she began dating actor Jason Schwartzman in 2003.
Known for his frequent collaborations with Wes Anderson, Schwartzman had already starred in the 1998 hit movie Rushmore when the two started their romance. Although Deschanel and Schwartzman aren’t a totally unexpected pair, their two-year relationship was kept pretty low key up until their breakup in October of 2005.
Katie Holmes and Chris Klein
Before Katie Holmes began dating now ex-husband Tom Cruise in April of 2005, she actually was in a relationship with American Pie actor Chris Klein. Holmes had already achieved fame as Joey Potter on the teen-drama television series Dawson’s Creek (1998-2003) when she met and began dating Klein in 2000.
They were together for five years — during which they became engaged — before breaking up in early 2005. Since their split, though, they have managed to remain friends over the years.
Edward Norton and Salma Hayek
Salma Hayek might be married to French businessman Francois-Henri Pinault at this moment in time. However, people forget that she used to date fellow actor Edward Norton. During the end of the 90s and the beginning of the 00s, Hayek was in a relationship with the American History X star.
Funny story: it turns out that they both had the same chiropractor and that’s how they ended up hitting it off! Nevertheless, they broke things off in 2003 and Hayek is now with Pinault.
Shia LaBeouf and Hilary Duff
There is no denying that Shia LaBeouf has had a rollercoaster ride of a career. With many highs and lows, the eccentric actor seems to have returned to a rich vein of form in recent times. Casual fans might have forgotten though about the extremely brief fling he ended up having with Hilary Duff, of all people.
LaBeouf revealed in an interview with Hollywood Life that their first date was “probably the worst date either of us have ever had.”
Josh Hutcherson and Vanessa Hudgens
It was clear that Vanessa Hudgens was in a vulnerable place after breaking up with High School Musical co-star Zac Efron. Shortly after, it is believed that Hudgens dated Josh Hutcherson, who she was working with on Journey 2: The Mysterious Island.
Hutcherson eventually confirmed that they were no longer dating. “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
Although it’s not the biggest surprise in the world that David Arquette and Drew Barrymore reportedly had a brief romance, it is a fact that many fans aren’t fully aware of. Even though Barrymore has vehemently denied such claims in the past, Arquette begs to differ.
He claimed that they started dating long before working together on Never Been Kissed. “We also dated, but she denied it on Howard Stern,” Arquette said on PeopleTV’s Couch Surfing.
Joaquin Phoenix and Liv Tyler
These days, Joaquin Phoenix has risen from the ashes of his bizarre acting hiatus to become once again, one of the most sought-after actors in all of Hollywood. Liv Tyler recalls the time that she dated the Joker star when they were both still young.
“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,” Tyler told Elle.
Matt Damon and Winona Ryder
He is famous for starring in films such as Good Will Hunting and The Bourne Identity, and she has just become a household name once again having starred in Stranger Things, but before all this, Matt Damon and Winona Ryder dated.
In fact, the famous pair dated for two years before sadly calling it quits on their romance in March 2000. Not all love was lost, however, because five years later Damon married his now wife, Luciana Barroso, and in 2011, Ryder married Scott Mackinlay Hahn.
Tom Cruise and Penelope Cruz
Tom Cruise has been married three times, and two of those were very high profile marriages. Following the breakdown of his second marriage to Nicole Kidman, Cruise met fellow actress, Penelope Cruz.
The pair met on the set of Vanilla Sky in 2000, and they remained a couple for the next three years, before calling it quits in January 2004. Two years later, Cruise married his third wife, Katie Holmes, who he later divorced, and Cruz married Javier Bardem in 2010.
Cameron Diaz and Justin Timberlake
Cameron Diaz is a successful actress worldwide, but before marrying her current husband, Benji Madden, in 2015, it seemed she was not having much success in her love life.
In fact, the What Happens In Vegas star had a string of long-term relationships with the likes of actor Jared Leto and baseball star Alex Rodriguez, but can you remember when Cameron dated Justin Timberlake? The actress met the singer in April 2003 and, although she was eight years older, they dated until January 2007.
Jennifer Garner and Scott Foley
Jennifer Garner and her ex-husband, Ben Affleck, made headlines for months when the media speculated that they were ending their marriage. The rumors were finally put to bed when the couple confirmed their shocking divorce, but this was not the first for 13 Going On 30 star.
A year before marrying Affleck, her divorce to her husband of three years, Scott Foley, was finalized. The couple met on the set of Felicity but, “We didn’t have a shot,” Garner told Allure. “He’s a really good guy, and we just imploded.”
Wilmer Valderrama and Lindsay Lohan
It is hard to keep up with the ongoings of Lindsay Lohan, but it cannot be forgotten that the former child star once dated That ’70s Show actor, Wilmer Valderrama.
They are perhaps a forgotten couple since Wilmer went on to have a long-term relationship with Demi Lovato, which caused enough controversy in itself. However, in July 2004, at Lohan’s 18th birthday, the secret was out of the bag that Lohan and Valderrama were in a relationship. It was not to last, however, and they split later that year.
Gwyneth Paltrow and Brad Pitt
They are two stars who have gone on to have very high-profile marriages, and subsequent divorces, but what could have once been, was Gwyneth Paltrow and Brad Pitt.
Before Chris Martin, Jennifer Aniston, or Angelina Jolie were in their lives, Paltrow and Pitt starred together in the 1995 film, Se7en. The couple was engaged at one point in their relationship but later called it off. Speaking to Howard Stern, Paltrow said, “I wasn’t ready, and he was too good for me.”
Alexis Bledel and Milo Ventimiglia
It was a good time when Gilmore Girls was still on the air and fans got to watch the likes of Alexis Bledel and Milo Ventimiglia together on screen.
Meanwhile, the actor and actress developed a relationship off-screen from 2003. That’s right, the couple took their Gilmore Girls romance to real life, and fans of the show rejoiced at the news. While the co-stars certainly made a beautiful pair, their romance was only to last three years, and they called it quits in 2006.
Kid Rock and Pamela Anderson
Kid Rock and Pamela Anderson have continued to make headlines over the years, and not always for good reasons. In 2003, the headlines were about their engagement and once again when they split up before even making it down the aisle.
However, while most couples go their separate ways after calling off their engagement, Anderson and Kid Rock infamously got married on a yacht in 2006. While fans may have believed this was the real deal, Anderson filed for divorce just four months later.