1. Chris Evans and Jessica Biel
Jessica and Chris started dating in 2001 and would go on to costar in two movies together — London and Cellular — before calling it quits in 2006.
Getty Images / Hulton Archive 2. Aubrey Plaza and Michael Cera
During a 2016 interview with RuPaul and Michelle Visage's now possibly defunct podcast, What's the Tee? , Aubrey revealed that she and Michael met on the set of Scott Pilgrim vs. the World and went on to date for about a year and a half.
Jeff Kravitz / FilmMagic 3. Zendaya and Jacob Elordi
Zendaya and Jacob allegedly started dating in 2019 after they wrapped the first season of Euphoria — though they never confirmed that they dated. The two were spotted hanging out together a lot, including photos of them kissing in NYC. However, reportedly , after COVID started, the relationship fizzled out as Zendaya was quarantining in LA, while Jacob was quarantining in his native Australia.
Filmmagic / FilmMagic / Getty Images 4. Emma Stone and Kieran Culkin
The pair met on the set of their 2009 film Paper Man and dated from 2010–11.
Bruce Glikas / FilmMagic / Getty Images 5. Macaulay Culkin and Mila Kunis
Mila and Macaulay were in a long-term relationship, dating from 2002 to 2011. While the two have never really spoken about their relationship, Mila did reveal to Dax Shepard on his podcast, Armchair Expert , that the breakup was bad, saying it was a "horrible, horrible breakup."
Christopher Polk / FilmMagic / Getty Images 6. John Krasinski and Rashida Jones
There was a good reason Rashida and John had great onscreen chemistry on The Office, and that's because the two had actually dated for about a year (2005–06) before Rashida joined the show — but, FTR, the two had already broken up when she came on.
Alberto E. Rodriguez / Getty Images 7. Rosario Dawson and Jason Lewis
Not too much is known about their relationship other than the two dated from 2004–06.
Mark Sullivan / WireImage 8. Josh Hutcherson and Vanessa Hudgens
The two briefly dated during the filming of their 2012 movie Journey 2: The Mysterious Island . And while promoting the film in Australia, the two were awkwardly put on the spot during a TV interview when they got asked about their relationship, to which Josh replied, "We’re not. We were at one point, but she broke my heart... No, I’m just kidding. That was a while ago. We’re really good friends now."
Christopher Polk / Getty Images for PCA 9. Salma Hayek and Edward Norton
The two began dating in 1999, after reportedly being introduced to each other by their chiropractor. The two broke up in 2003, but the world found out after Daryl Sabara accidentally revealed it in an interview on Today — while promoting Spy Kids 3-D: Game Over (a movie Salma also costarred in) — where he said, "She isn’t with Ed Norton anymore."
Dan Macmedan / WireImage 10. Leighton Meester and Sebastian Stan
The two met on the set of Gossip Girl in 2007 (when Sebastian began appearing as the recurring character of Carter Baizen) and dated from 2008 to 2010.
Patrick McMullan / Patrick McMullan via Getty Images 11. Zachary Quinto and Jonathan Groff
The two dated for almost a year (2012–13) before calling it quits — reportedly because their work schedules kept them apart. However, the two have remained friends following the breakup.
Matt Winkelmeyer / Getty Images for GQ 12. Emilia Clarke and Seth MacFarlane
The two dated from Sept. 2012 through March 2013, and reportedly split up because it was a long-distance relationship. At the time, Emilia was filming Game of Thrones in Europe, while Seth was based in LA.
FilmMagic / Getty Images 13. Penélope Cruz and Matthew McConaughey
Penélope and Matthew met on the set of their 2005 film Sahara , and would go on to date for almost two years before calling it quits.
Eduardo Parra / FilmMagic 14. Cameron Diaz and Alex Rodriguez
Cameron and Alex dated for over a year — between 2010–11. After their breakup, Alex told People , "I have a lot of love for Cameron. We’ll always be friends."
George Pimentel / Getty Images 15. Keira Knightley and Jamie Dornan
Keira and Jamie dated from 2003 to 2005, when he was still a model and her career was taking off. A few years after their breakup, Jamie told the Mail on Sunday that he felt "a bit second-rate" compared to her, and that put pressure on their relationship.
Evan Agostini / Getty Images 16. Michelle Rodriguez and Cara Delevingne
Cara and Michelle dated for a few months in the beginning of 2014 before calling it quits . And the breakup seems to have been an amicable one .
James Devaney / WireImage / Getty Images 17. Hilary Duff and Joel Madden
The two dated from 2004 to 2006. In a 2016 interview with The Love Bomb with Nico Tortorella podcast, Hilary opened up about the relationship, saying it "was so intense. It was my life," and that "it was pretty major." The two are friends, though, and even went on a group date together recently.
Jeff Kravitz / FilmMagic, Inc / Getty Images 18. Kristen Wiig and Fabrizio Moretti
The pair started dating in early 2012 and broke it off in July of 2013 . However, this does actually seem to be one of those breakups that actually was amicable as the two were spotted hanging out together at a Knicks game in November of 2013.
Steve Jennings / WireImage / Getty Images 19. John Mayer and Katy Perry
John and Katy dated on-again, off-again from 2012 until 2015. After the breakup, the two have only spoken kindly of each other — with John telling Andy Cohen on his Sirius XM radio show last year that there was no jealousy in the relationship and that he liked being the "first gentleman of Katy Perry."
Christopher Polk / Getty Images for NARAS 20. Kirsten Dunst and Jake Gyllenhaal
Jake and Kirsten dated from 2002 to 2004 and were introduced to each other by his sister, Maggie Gyllenhaal (who had costarred with Kirsten in Mona Lisa Smile ).
Kevin Winter / Getty Images Entertainment 21. Suki Waterhouse and Diego Luna
Suki and Diego met on the set of their 2016 film The Bad Batch, and dated for over a year before they ended it in 2017.
Team Gt / GC Images 22. Bow Wow and Ciara
The two dated from 2004 to 2006 and were even briefly engaged. In 2021, Bow Wow spoke out on Twitter (I am not calling it X) about fans still blaming him all these years later for their breakup.
Kevin Winter / Getty Images 23. Rachel McAdams and Michael Sheen
The two met on the set of their 2011 film, Midnight in Paris, and were together until 2013. Reportedly, the two split because Rachel wanted to settle down and start a family, while Michael — who had already been married and had a child — wanted to focus more on his career.
Anthony Harvey / Getty Images 24. Sofia Coppola and Quentin Tarantino
After her divorce from fellow director Spike Jonze in 2003, Sofia Coppola found herself in a relationship with another director: Quentin Tarantino. They would go on to date for two years, and even after their breakup, they remain good friends to this day.
Evan Agostini / Getty Images 25. Renée Zellweger and Bradley Cooper
Renée and Bradley first met in 2006 during the filming of their movie Case 39 — which was a film that ended up being shelved in the States until 2010 — when they were both married. But the two wouldn't start dating until the summer of 2009 (after both had separated from their spouses) and eventually split less than two years later in 2011.
Randy Brooke / WireImage / Getty Images, Vera Anderson / WireImage / Getty Images 26. Alanis Morissette and Ryan Reynolds
The Canadian power couple began dating in 2002 and became engaged in 2004. After five years together, the pair called off their engagement in 2007.
Albert L. Ortega / WireImage / Getty Images 27. Ben Affleck and Gwyneth Paltrow
Ben and Gwyneth are both no strangers to high-profile romances, so it's easy to forget that they dated from 1997–2000. They also starred in two movies together during that time: Shakespeare in Love and Bounce .
In May of this year, Gwyneth appeared on the Call Her Daddy podcast , where host Alex Cooper asked who was better in bed: Brad Pitt or Ben, to which she replied that was a tough question...but that "Ben was, like, technically excellent!"
Kevin.mazur / WireImage28. Tom Cruise and Sofía Vergara
Reportedly , the two where set up by Will Smith, who invited Sofía to a pre-Oscars party and introduced her to Tom in Feb. 2005. Tom then allegedly kept calling her and sending flowers and chocolates. However, they were only photographed on one date that same month.
Bauer-griffin / GC Images 29. Brittany Murphy and Ashton Kutcher
The two dated briefly in 2003 after meeting on the set of their rom-com, Just Married . In 2009, following Brittany's death, Ashton took to Twitter to express his sadness, tweeting , "2day the world lost a little piece of sunshine. My deepest condolences go out 2 Brittany's family, her husband, & her amazing mother Sharon. See you on the other side, kid."
Frank Micelotta / Getty Images Entertainment 30. Russell Crowe and Meg Ryan
This was a bit of a scandal at the time, as Meg was married to Dennis Quaid when she met Russell on the set of their 2000 movie Proof of Life. It was announced that Meg and Dennis were separating during filming, and people quickly assumed that it's because she had started an affair with Russell.
Meg was labeled as an adulteress — which hurt her Hollywood image — and her and Russell's relationship ended about six months later. To add insult to injury, the bad publicity is sited as being a big reason as to why the movie bombed at the box office. However, in the years since, Meg has been clear to correct the narrative and say that her and Dennis's marriage had been over long before she met Russell and that he had nothing to do with their divorce.
Steve Granitz / WireImage 31. Jason Schwartzman and Zooey Deschanel
Their exact dating history is not completely clear. But in an interview , Zooey said that she and Jason started dating in 1999, when they were both 19, and that he was her first "real boyfriend." The two then broke it off at some point and then rekindled their romance, dating from 2003 to 2005.
Gregg Deguire / WireImage / Getty Images 32. Whitney Houston and Ray J
While Whitney and Ray J never confirmed their relationship, the two reportedly dated on-again, off-again starting around 2007 and were rumored to be together at the time of her death in 2012. In 2017, Ray J was a contestant on Celebrity Big Brother UK and blamed himself for her death on the show.
John Gichigi / Getty Images 33. Jennifer Aniston and Vince Vaughn
Jennifer and Vince met in 2005 on the set of their film, The Break-Up . The two dated for about a year before breaking up in real life in 2006. But the romance was significant because it was her first relationship after splitting with Brad Pitt. In a 2008 interview with Vogue, Jennifer had this to say about him and their relationship: "I call Vince my defibrillator. He literally brought me back to life... He was lovely and fun and perfect for the time we had together. And I needed that. And it sort of ran its course."
Universal / ©Universal/Courtesy Everett Collection 34. Scarlett Johansson and Josh Hartnett
The pair dated for a little over a year after meeting on the set of their 2006 film, The Black Dahlia .
Jeff Vespa / WireImage / Getty Images 35. And lastly, Ryan Gosling and Sandra Bullock
Ryan's first high-profile romance wasn't with Rachel McAdams — it was actually with Sandra. The two met in 2002 on the set of their film, Murder by Numbers, and dated for about a year.
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