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  3. These Stars Worked Together Despite Their Romance Not Working Out

These Stars Worked Together Despite Their Romance Not Working Out

Amanda Stanford / December 8, 2023 - 11:50 pm

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Pinterest Premiere Of Summit Entertainment's "The Twilight Saga: Breaking Dawn - Part 2" - Red Carpet
(© 2012 Getty Images)

Robert Pattinson and Kristen Stewart

Everyone remembers when Robert Pattinson and Kristen Stewart were getting cozy amid their Twilight saga filming, and the cheating scandal that sent it all spiralling down! Unfortunately, the couple broke up before their press tour for the final installment in the series hit theatres, and the couple had to continue doing interviews together despite the world knowing of their dramatic split! Yikes!

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Pinterest 2002 MTV Video Music Awards
(© 2002 Getty Images)

Tony Kanal and Gwen Stefani

Music icons and '90s "it" couple Gwen Stefani and Tony Kanal had to break up in the middle of the huge success of their new album, Tragic Kingdom. Despite the separation, the two continued to tour as bandmates for another album and tour before retiring from the band for good. 

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Pinterest These Stars Worked Together Despite Their Romance Not Working Out
(© 2006 Getty Images)

Alexis Bledel and Milo Ventimiglia

While Alexis Bledel and Milo Ventimiglia played an onscreen on-and-off-again couple for Gilmore Girls, in real life things were getting heated too! Unfortunately, the couple broke up after the final season of the show - but that didn't stop them from being buddies years later when they had to work together once more for the Netflix release Gilmore Girls: A Year In The Life. 

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Pinterest These Stars Worked Together Despite Their Romance Not Working Out
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Katie Holmes and Joshua Jackson

Dawson's Creek stars Katie Holmes and Joshua Jackson coupled up while they were filming the television series, and all was well... until it wasn't! The couple broke up before the series ended, and they had to continue working together for a few more seasons of the series. 

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Pinterest These Stars Worked Together Despite Their Romance Not Working Out
(© 2011 Getty Images)

Cameron Diaz and Justin Timberlake

Two beauties Justin Timberlake and Cameron Diaz dated for four years, working together during their coupling on films like Shrek the Third, before ultimately calling it quits in 2007. Four years later, though, the couple joined forces once more, only as colleagues this time. They worked on the film Bad Teacher and did press releases and red carpets as if nothing happened between them!

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Pinterest These Stars Worked Together Despite Their Romance Not Working Out
(© 2010 Getty Images)

Drew Barrymore and Justin Long

Hollywood alum Drew Barrymore started dating Justin Long after they met on the set of He's Just Not That Into You, a rom-com that was filled to the brim with A-listers! However, after a year of dating the two ended things. It didn't stop them from working on another project after their split, Mad About You, another romantic film. Awkward!

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Pinterest These Stars Worked Together Despite Their Romance Not Working Out
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Rachel Bilson and Adam Brody

Anyone who is a fan of the early naughties series The O.C would remember the fan-favourite couple "Seth" and "Summer"! In real life, the two actually did form a relationship, but it didn't last! The couple broke up behind cameras, but their characters remained together until the end of the series. 

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Pinterest 'These Stars Worked Together Despite Their Romance Not Working Out
(© 2010 Getty Images)

Jennifer Carpenter and Michael C Hall

Dexter stars Jennifer Carpenter and Michael C. Hall may have played siblings on the show, but the farthest thing was the truth off-set! The two dated during the height of the show and even got married before splitting up in 2011. The pair still had to film for two more years.

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Pinterest These Stars Worked Together Despite Their Romance Not Working Out
(© 2009 Getty Images)

Blake Lively and Penn Badgley

Yup, that's right, "Serena" and "Dan" were coupled in real life, too! Of course, Blake Lively and Penn Badgley didn't last, since Lively is now married to Ryan Reynolds, but there was a time when our Gossip Girl fantasies were real! The two broke up in 2010 and still had to pretend for two more years while the last two seasons of the show were filmed. 

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Pinterest These Stars Worked Together Despite Their Romance Not Working Out
(© 2016 Getty Images)

Johnny Galecki and Kaley Cuoco

Don't worry if you had no idea these two were dating - they kept it a secret from everyone! Johnny Galecki and Kaley Cuoco dated secretly in the first seasons of The Big Bang Theory, and when they split it could have been worked out they wouldn't have to keep working together. That is until writers made "Leonard" and "Penny" an item! It worked out okay in the end, as the two of them to this day share they're great as friends!

Awkward! Could you imagine working with your ex? Some celebs had no choice! Whether it was during TV series or movies, workplace romances aren't always a dream come true!

These Stars Worked Together Despite Their Romance Not Working Out

Celebs like Cameron Diaz and Justin Timberlake managed to leave a large gap between their breakup and films, but others weren't so lucky! 

Adam Brody and Rachel Bilson had to break up a good full season before the end of their show The O.C. And, to make matters worse, the two were a full-blown couple in front of the camera, meaning they still had to kiss and cuddle even when they were in the midst of a sad break-up! Talk about awkward!

Find out more above! 

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