Celebrity Couples Who Worked Together After a Breakup

Cleary these people are not petty like us.

By Claire Downs

Dating a co-worker is a little different for famous people. It’s nothing like the 9-to-5 troubles you and I might have with our little office bae. What happens when the magic ends? There’s always a risk that they won’t just run into each other at the water cooler; they might have to actually co-star in a movie together. Most people can barely stand to see a former flame’s status update on their socials, much less appear on a reality show together. Here are some celebs who took the high road by working with their exes.

  • 1 Cameron Diaz and Justin Timberlake
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    The A-list Hollywood couple dated for nearly four years before parting ways in 2007. In 2011, the pair rekindled their friendship while co-starring in the hilarious comedy Bad Teacher.

  • 2 Sarah Silverman and Jimmy Kimmel
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    Since their split in 2009, Silverman has appeared as a guest on Kimmel’s late night show several times. She has acted in sketches on the show, even ones about their breakup like the super funny I’m F*cking Matt Damon.

  • 3 Vivica A. Fox and 50 Cent
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    The couple started dating back in 2003, but by 2005 they split and were airing their dirty laundry in interviews. That’s why it surprised many people to see But, Vivica co-starring as an angry ex in Fif’s “Do You Think About Me” music video in 2009. Their feud was reignited just last year with a messy Instagram war.

  • 4 Kristen Stewart and Robert Pattinson
    Bella and Edward’s romance in the Twilight movies was so powerful that it sparked an IRL situation between Stewart and Pattinson. Unfortunately, life did not imitate their fairy tale onscreen romance. The couple broke up during the making of the last Twilight movie in 2012. That meant they spent a half-year doing a worldwide press tour together.

  • 5 J.Lo and Marc Anthony

    J.Lo and Anthony filed for divorce in 2011, right in the middle of filming segments for their reality competition show, Q’Viva! The Chosen. Their split actually made for great TV, because as judges, they often bickered on screen and once Lopez even playfully slapped Anthony.

  • 6 Rihanna and Chris Brown
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    Their tumultuous relationship went off the rails in 2009 when Brown infamously assaulted Rihanna. Despite pleas from fans not to reunite, the couple gave love another try in 2011 Brezzy was featured on the remix to RiRi’s single “Birthday Cake.” They recorded “Nobody’s Business” the next year, before officially ending things in 2013.

  • 7 Denise Richards and Charlie Sheen
    After divorcing in 2006, Richards guest-starred on an episode of Sheen’s sitcom Anger Management in 2013. The ex-lovers even had a couple of make-out scenes together.

  • 8 Bow Wow and Angela Simmons
    After dating on and off for years, Angela Simmons and Bow Wow found themselves in the awkward position of co-hosting BET’s “106 & Park” in 2013. It was all good though. Their friendship was too strong for any on-screen messiness.

  • 9 Michael C. Hall and Jennifer Carpenter
    After meeting on the set of Dexter, where they played brother and sister, Hall and Carpenter eloped in 2008. Their tumultuous 2-year marriage (Hall battled Cancer and Carpenter became jealous of co-star Julia Stiles) ended in 2010. To make things weirder, it was around that same time that the writers of the show added an incestuous twist to the characters Awkward!

  • 10 Gwen Stefani and Tony Kanal
    if Tony had never broken Gwen’s heart, the world would have never known about No Doubt. Shortly after the band was formed in 1991, Gwen started secretly dating bandmate Tony Kanal. The two broke up while the band was recording their third (and most famous album), Tragic Kingdom. Several of the hit songs on the album written by Stefani, “Don’t Speak,” “Just a Girl” and “Spiderwebs” were all about Kanal.

  • 11 Gwyneth Paltrow and Ben Affleck
    After landing her breakout role in Shakespeare in Love, Gwyneth Paltrow fell in love with co-star Ben Affleck sometime around 1992. The two had an on-again-off-again relationship, that never seemed to go full commitment. By 1999, the pair had been broken up for several years, but Affleck convinced Paltrow to work on his rom-com “Bounce.” The two rekindled their romance for a year during filming of the movie, until they broke up for good in 2000.

  • 12 Rachel Bilson and Adam Brody
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    Summer and Seth of The O.C. made love last longer than Bilson and Brody. The IRL couple broke up in 2006, but the show romance ran until 2007.

  • 13 Katie Holmes and Joshua Jackson
    Joey (Holmes) ultimately chose Pacey (Jackson) in the Dawson’s Creek love triangle, but the real life couple didn’t find the same magic. They broke up long before the show ended in 2003. [/item