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The stars met on the set of He's Just Not That Into You in 2007 and continued a romantic relationship for about a year. In 2010, they reunited as friends for the film Going the Distance.
These two met on the set of Gifted in 2016 and fell for each other on and off screen. They ended their romantic relationship soon after, but rejoined as friends to promote the film.
The comedic pair split in 2009 but remained close co-workers and friends. Since the breakup, Silverman has made appearances on Kimmel's late-night show and even made light of their split in a sketch.
During the third season of Gossip Girl, the pair decided to give their love a go until they ended things around 2012.
This pair met while filming House in 2004, and got serious enough to even get engaged. The two broke up shortly after but continued their onscreen engagement until Season 5 when their characters actually got married. Talk about awkward!
In 2003, the former co-stars played a couple on Alias. Although their IRL romance only lasted about a year, the two remained very professional while continuing to work alongside each other through 2006.
The former couple dated for about a year in 2014 (and were even rumored to be engaged), until the actress called it quits in 2015. The two reunited while promoting The Last Face, which Theron starred in and Penn directed.
These celebs dated while filming Dawson's Creek throughout the '90s, but continued to act together until the show ended in 2009.
While the lifestyle guru was working on her breakout role in 1997's Shakespeare in Love, the co-stars fell for each other. After three years, the A-listers went their separate ways but continued to work together when promoting their film, Bounce.
These two made history while starring alongside each other in the gangster classic trilogy, The Godfather. Just as their character's romance fizzled, the two struggled to keep the flame burning during the two decades that they dated on and off.
In 2015, the musical couple divorced after two years of marriage. Even after the split, the two combined talents and made music together.
The actors met while playing onscreen love interests on Gilmore Girls. They dated IRL for three and a half years, and although Milo had already left the show when they broke up, he did return as a guest star in later seasons.
Although they ended their relationship, The Office co-stars remained close friends while Novak appeared on The Mindy Project. Kaling even brought Novak as her date to Vanity Fair's 2018 Oscar party.
After seven years together, the No Doubt members broke up at the peak of the band's fame, but continued to perform together for years to come.
The Twilight co-stars called it quits after Stewart was caught cheating with director Rupert Sanders. The relationship got even more complicated when, after the scandal, the two had to work together to promote the newest sequel, The Twilight Saga: Breaking Dawn Part 2.
The former One Tree Hill stars fell in love while filming and got hitched in 2005. They'd divorce five months later, and had no choice but to keep their professional relationship strong while filming the show for another seven years.
The two started dating while filming Gossip Girl and had to awkwardly continue the onscreen romance as their characters', Dan and Serena, relationship grew stronger.
Although their O.C.'s characters' love lasted, the two broke up in 2006 and continued to work together until the show ended a year later.
The former American Idol contestant and Twilight star filed for divorce in 2014 but continued to work on the album, I'm Not Falling, together that they began before they married.
The two Big Bang Theory stars dated in real life just as their characters did on the show. Kaley and Johnny didn't last, but they remain close friends to this day.
The two played siblings onscreen for the show Dexter and continued that love off-screen in a very different way. They got married in 2008, but after divorcing three years later, had to put all awkwardness aside and continue acting alongside one another until the show ended in 2013.
The two were longtime friends and co-stars on The Vampire Diaries before they started dating. They ended things after three years, but continued to remain amicable as the seasons continued.
If there ever was an example of how exes should get along, it's these two! They broke up in 2006, but reunited for the 2011 film, Bad Teacher.
The famous pair filed for divorce in 2014, but continue to be business partners, friends and co-parents while working on their show Q'Viva! The Chosen.