21.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.
22.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.
23.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.
24.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.
25.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.
26.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.
27.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.
28.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.
29.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.
30.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.
31.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.
32.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.
33.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.
34.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.
35.50 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.
36.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.
37.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.
38.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.”
39.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.
40.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.
41.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.
42.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.”
43.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!
44.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!”