READ THIS NEXT: The Most Compatible Celebrity Couples, According to the Zodiac. Not long after her split from Brad Pitt, Jennifer Aniston hit it off with her co-star in the 2006 comedy The Break-Up, Vince Vaughn. While their romance only lasted for about a year, it seems that they still think pretty highly of each other. Speaking to Playboy in 2015 (as reported by HuffPost), Vaughn said that while Aniston was “great,” he wasn’t as big of a fan of the paparazzi attention involved in dating a super-famous woman who was just out of one of the tabloids’ favorite relationships. Later, The Amazing Spider-Man co-stars Emma Stone and Andrew Garfield would become an item, as would current Peter Parker Tom Holland and his leading lady, Zendaya. But the Spidey on/off-screen romance that started it all was between Tobey Maguire and Kirsten Dunst, who starred in the trilogy that began in 2002. While there was gossip, the relationship wouldn’t be confirmed until later, by their director. Sam Raimi told The Sydney Herald in 2007, as reported by E!, that Maguire and Dunst “broke up before the second movie,” 2004’s Spider-Man 2. Fortunately, the film wouldn’t suffer for it. “I was concerned they wouldn’t get the same chemistry back, but it was just me worrying,” the director said. “They really like each other, I think, very much. And that relationship probably just added to their ability to trust each other.” Were you a Team Jess Gilmore Girls fan? Then you were no doubt also invested in the real-life relationship between Milo Ventimiglia and Alexis Bledel. The costars dated for several years, beginning in 2002. They mostly kept things pretty private, but in 2005, Bledel confirmed to People that they had, at one point, floated the idea of getting married. By the middle of 2006, however, they were done. Slumdog Millionaire was a massive success in 2008, propelling both leads to international stardom. Fortunately, Freida Pinto and Dev Patel had each other to lean on throughout the process. Their director, Danny Boyle, told the Associated Press that he “was the last to know” that the co-stars were falling in love during filming, but so they did—and they would go on to date for six years before splitting in 2014. For more celebrity relationship trivia sent right to your inbox, sign up for our daily newsletter. In actor Curtis Armstrong’s memoir Revenge of the Nerd, the Risky Business star claims that Tom Cruise and Rebecca De Mornay enjoyed a steamy affair while filming the 1983 film. Neither of the actors involved in this supposed relationship has ever commented publicly on their connection, but stranger things have certainly happened.ae0fcc31ae342fd3a1346ebb1f342fcb Tom Cruise’s relationship with his Vanilla Sky co-star Penélope Cruz was much more public. Cruise claimed to The Telegraph that their working dynamic didn’t become romantic until after filming wrapped—and after Cruise was divorced from Nicole Kidman—but it certainly increased interest in the film. The pair broke up after nearly three years together in 2004, and while the public statements from their teams pointed to an “amicable” split, sources told Vanity Fair that Cruz’s unwillingness to become a Scientologist had something to do with it. Though Joey Potter infamously chose Pacey Witter over Dawson Leery in the series finale of Dawson’s Creek, the real-life romance between Katie Holmes and Joshua Jackson started—and ended—long before. Holmes told Rolling Stone in 1998 (as reported by Us Weekly), when Dawson’s was still very much the hottest teen show on TV, that Jackson was her “first love.” “I feel so fortunate because he’s now one of my best friends,” the star continued. “It’s weird, it’s almost like a Dawson-and-Joey type thing now.” Unlike most of the other couples on this list, Matt Dillon and Cameron Diaz were already an item by the time they worked together. The actors met in 1995, started seeing each other in 1996, and in 1998, they appeared opposite each other in the gross-out comedy There’s Something About Mary. But soon after it arrived in theaters, they broke up. According to Dillon, distance was a factor. “Look, I loved her and we were very close, but it just ran its course,” he told Rolling Stone. “We’re both actors, she was living in L.A., and I was living in New York, and I didn’t want to commit to moving out there. But I don’t want to say it was about any of those things. It just ran its course.” Summer Roberts and Seth Cohen of The O.C. were undoubtedly one of the most beloved TV couples of the ’00s, and the chemistry between the actors who played them bled into their real lives. Rachel Bilson and Adam Brody dated from 2003 and 2006, and as recently as 2020, they were still aware of how much their fans loved seeing them together. Responding to an Instagram post by InStyle magazine of some of their cutest moments (as reported by People), Bilson commented, “IM SORRY!!!! He fared really well!” While she reportedly split from Bill Hader also in 2020, Brody is married to fellow teen TV idol, Gossip Girl star Leighton Meester. If you missed Matthew McConaughey’s 1996 love affair with his A Time to Kill co-star Sandra Bullock, that may be because they kept their tryst a secret. In fact, Bullock didn’t confirm that they had been anything other than colleagues until 2003 in an interview with Cosmopolitan. “There’s a great amount of respect and love,” she said, when asked how they stayed friends after splitting. “I feel very cared for by Matthew.” You may know that Zoe Saldana and Bradley Cooper are co-stars in the Guardians of the Galaxy series, but you might not be aware that they had previously worked together, in a movie where she wasn’t green and he wasn’t a raccoon. The actors co-starred in the little-seen 2012 mystery drama, The Words, and were also an item around that time. According to Us Weekly, they broke up for good at the end of that year. Fortunately, their past didn’t preclude their future team-up in the Marvel Cinematic Universe. Liv Tyler and Joaquin Phoenix starred together in the dreamy 1997 romantic drama Inventing the Abbotts, and they also started a romance off-screen. “I fell in love the moment I saw him,” Tyler told The Morning Call in 1997, also explaining that they took care to keep their relationship a secret on set. Though the actors broke up after three years together, they’ve remained close in the ensuing years. In 2015, Tyler told Elle that Phoenix was “like family.” Sure, they were big news to the teen set when they got together, but over time, you’ve probably forgotten that Zac Efron and Vanessa Hudgens were basically the prom king and queen of the Disney Channel for several years. The High School Musical co-stars dated from 2005 to 2010, but sadly, don’t seem to be in touch anymore, even as pals. Post-Cruise and Bullock, Penélope Cruz and Matthew McConaughey hooked up on the set of 2005’s Sahara. They only lasted for a year, but soon after, both would soon start seeing their future (and current) spouses: Camila Alves for McConaughey and Javier Bardem for Cruz. It wasn’t a well-reviewed movie or a long-term relationship, but Valentine’s Day couple Taylor Swift and Taylor Lautner were a thing for a few sweet months in 2009. It’s been theorized that her 2011 hit “Back to December” may be about their split. Dominic Cooper and Amanda Seyfried went from co-stars to lovers to being co-stars again. They met on the 2008 movie musical Mamma Mia! and went on to date off and on for about four years. Then, seven years later, the exes joined forces onscreen again in the 2018 sequel Mamma Mia! Here We Go Again. Despite the awkwardness of returning to play two characters who were still in love, Cooper told Attitude (via ET Online) that they made it through just fine. “She’s a friend,” he said of Seyfried. “It was always going to be OK. You just have to be delicate with those situations.” Blake Lively and Penn Badgley weren’t the only real-life couple to come out of Gossip Girl. Leighton Meester and Sebastian Stan also took their love story off-set. The two dated for two years in the late 2000s, and sources said that it was Meester who initiated the breakup. Neither Amanda Bynes nor Channing Tatum ever confirmed that they dated during filming of their 2006 romantic comedy She’s the Man, but rumors flew thanks to some paparazzi shots of the two kissing. And Tatum is still grateful to his co-star for championing him for what would be a breakout role. “She definitely helped,” Tatum told Sky News in 2018. “Man, I thank her every day.”
