Can You Say ‘Awkward’? These Celebrity Exes Worked Together After Breaking Up

Lots of people in Hollywood meet their romantic partners on the job. When you spend hours a day working with someone on a TV series, film, or even a music album, some off-set or out of studio chemistry is bound to happen. While finding a little romance on the job is nice, it can also get super awkward when the relationship fails and the two parties still have to work together. The following celebs hit it off, broke it off, and somehow managed to put their differences aside to get their paychecks.

Charlize Theron and Sean Penn Had to Promote a Film After She Allegedly Ghosted Him

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Mike Marsland/WireImage
Mike Marsland/WireImage

Charlize Theron and Sean Penn started dating in 2013 and reportedly got engaged the following year. The couple ended their relationship in 2015. Just a year later, they promoted the film The Last Face together, which Penn directed and Theron starred in. The media widely reported that Theron dumped Penn by “ghosting” him.

But Theron insisted she didn’t ghost Penn by refusing to return his calls. She told WSJ magazine, “The [expletive] ghosting thing, like literally, I still don’t even know what it is. It’s just its own beast.” She added, “We were in a relationship and then it didn’t work anymore. And we both decided to separate. That’s it.”

Gwyneth Paltrow Persuaded Ex-Boyfriend Ben Affleck to Star With Her on Bounce

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Ke.Mazur/WireImage
Ke.Mazur/WireImage

It’s been so long you may have forgotten that Gwyneth Paltrow dated Ben Affleck after they worked together on the 1997 film Shakespeare in Love. They dated for three years before splitting up in 1999. Then they worked together on the 2000 film Bounce. They rekindled their relationship and then split up again.

Paltrow told Howard Stern in 2018 of their relationship: “It’s interesting, I think there’s certain boyfriends where you are trying to work stuff out, right? Like, you’re trying to heal certain stuff from your childhood and he was very much a lesson in that way.”

Jennifer Morrison and Jesse Spencer Broke up in Real Life Then Got Married on TV

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Barry King/WireImage
Barry King/WireImage

Jennifer Morrison and Jesse Spencer met on the set of the medical drama House in 2004. The pair got engaged in 2006 when Spencer proposed in Paris, but they broke it off. Interestingly, their characters were also involved with each other and got married in season five.

In 2008, Morrison talked about how the pair got through the kissing scenes on House after they broke up in real life. She revealed in an interview that they avoided actually kissing each other during rehearsals. “Out of respect, I saved it for the take,” she said of the scenes.

Drew Barrymore and Justin Long Made a Movie Together After Their Split

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Gregg DeGuire/FilmMagic
Gregg DeGuire/FilmMagic

Like many actors, Drew Barrymore and Justin Long met on set. The pair kindled their romance in 2007 while making He’s Just Not That Into You. The couple dated for about a year before splitting up in 2008. Two years later, they worked together again in the movie Going The Distance.

The twosome has maintained a friendly relationship over the years. As recently as 2018 they were spotted together at the Lowell Hotel in New York City. Both were single at the time. Barrymore’s four-year marriage to Will Kopelman was over, and Long was no longer dating singer Lauren Mayberry. Who knows, maybe they’ll give it another go!

These Big Bang Theory Stars Still Work Together 10 Years After Their Romance Failed

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BAlberto E. Rodriguez/Getty Images
BAlberto E. Rodriguez/Getty Images

Kaley Cuoco and Johnny Galecki dated for two years while working together on The Big Bang Theory. Their characters were simultaneously dating. The real-life couple split in 2009, yet they continue to work together a decade later. The duo are good friends and colleagues even today.

Galecki attended Cuoco’s wedding in 2018. When late-night host James Corden asked if it was strange, Galecki responded, “Not at all. It was a beautiful wedding.” He also posted a photo of them on Instagram, writing, “Couldn’t be happier for my fake wife @normancook and @mrtankcook whose words brought us all to tears last night. So much love for you both.”

Chris Evans Had to Promote a Film With His Ex-Girlfriend Jenny Slate

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Emma McIntyre/Getty Images
Emma McIntyre/Getty Images

Actor Chris Evans started dating actress-comedian Jenny Slate after the pair met on the set of Gifted in 2016. Around the same time, Slate split with her filmmaker husband, Dean Fleischer-Camp. The couple had a short-lived relationship and were no longer together by the time they promoted the film as friends.

Slate told New York Magazine after the breakup, “Chris is truly one of the kindest people I’ve ever met, to the point where sometimes I would look at him and it would kind of break my heart. He’s really vulnerable, and he’s really straightforward. He’s like primary colors. He has beautiful, big, strong emotions, and he’s really sure of them.”

Sarah Silverman Makes Guest Appearances on Ex-Boyfriend Jimmy Kimmel’s Late-Night Show

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Alberto E. Rodriguez/Getty Images for Disney
Alberto E. Rodriguez/Getty Images for Disney

Sarah Silverman began dating Jimmy Kimmel in 2002. They split in summer 2008 but got back together that fall. They split for good in March 2009. Silverman continued to appear on Kimmel’s late-night show. In 2019, Silverman posed alongside Kimmel and his wife at the Golden Globe Awards.

Silverman was pictured in the foreground looking pained, while Kimmel and Molly McNearney were hugging behind her. Silverman captioned the image, “Good times.” A few months earlier, SIlverman was a guest on Kimmel’s show and joked about waiting for Kimmel’s “tryst” to be over with his wife, with whom he shares two kids.

Gwen Stefani and Tony Kanal Kept Making Music Together After They Split

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Tim Mosenfelder/Getty Images
Tim Mosenfelder/Getty Images

Gwen Stefani started dating No Doubt bassist Tony Kanal shortly after she joined the band in the late ’80s. Their relationship was so intense, the band nearly broke up after the couple called it quits. Their failed romance inspired many of their songs, including “Don’t Speak,” “Sunday Morning” and “Hey You!”

In 2016, Stefani admitted it was still strange to sing the song “Don’t Speak” because of all the memories. She told Howard Stern: “It’s still weird. Even last night when I sang the song it’s still weird. I just rolled my eyes and walked away [like] really? You’re still feeling that?”

Jennifer Garner and Michael Vartan Worked Together for Two Years Post-Break Up

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Albert L. Ortega/WireImage
Albert L. Ortega/WireImage

Jennifer Garner and Michael Vartan were costars on the action drama Alias. Their romance waned after about a year in 2004, but the pair still had to work together until the show ended in 2006. Despite what could have been an awkward situation, the pair remained friends.

In 2018, Garner celebrated her ex’s birthday, posting a photo of the two of them from the Alias set and writing: “Can you believe this baby face is 50?! Happy birthday, #MichaelVartan #alwaysanALIASgirl#sydneyandvaughnforever.” They were both single at the time, but Vartan told E! earlier that year, “If it didn’t work once, there’s a reason it didn’t work.”

Katie Holmes and Joshua Jackson Split up Two Seasons Into Dawson’s Creek

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Tom Kingston/WireImage
Tom Kingston/WireImage

Katie Holmes and Joshua Jackson fell in love on the set of Dawson’s Creek in the ’90s. They were together for the first two seasons, and Jackson was reportedly Holmes’ first true love. They split up but remained costars until the program ended after season six in 2009.

The pair remained friendly over the years. In 2012, Holmes reached out to Jackson out of the blue. “Like any old friend, it was like, ‘Oh, hi how are ya? What’s going on?’; ‘I had a kid,'” Jackson told Us Weekly about the unexpected phone call.

Avril Lavigne and Chad Kroeger Still Make Music Together

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Taylor Hill/Getty Images
Taylor Hill/Getty Images

Avil Lavigne started dating Nickleback singer Chad Kroeger in 2012 while they were working together on her fifth album. They got engaged within a month and tied the knot in 2013. They split up two years later in 2015. The former couple continue to make music together after their divorce.

“He was with me through a lot and is a really protective person in my life. He’s still like family,” Lavigne said in 2019. “I didn’t know that it would be that way, and I’m really glad it is because we were friends and we made music together. We’ve just kept the friendship and continued having a working relationship, as well.”

Alexis Bledel and Milo Ventimiglia Reunited on Gilmore Girls 10 Years After They Broke Up

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Joe Schildhorn/Patrick McMullan via Getty Images
Joe Schildhorn/Patrick McMullan via Getty Images

Alexis Bledel and Milo Ventimiglia played love interests on Gilmore Girls and started dating in real life in 2002. They split up after three and a half years together in 2006. While Milo was no longer a regular star on the show, he appeared as a guest in several episodes after they broke up. They also both returned for the 2016 Gilmore Girls reboot.

While they didn’t work out, they were pretty serious and even discussed marriage. “I think everybody who has been dating for more than a couple of years probably talks about it at some point,” Alexis told People in 2005.

B.J. Novak Appeared on Mindy Kaling’s Sitcom After They Split

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Matt Winkelmeyer/VF19/WireImage
Matt Winkelmeyer/VF19/WireImage

Mindy Kaling and B.J. Novak met while working on The Office together. The pair had an on-again-off-again relationship while writing and acting on the sitcom. Their characters, Ryan Howard and Kelly Kapoor, also dated on and off. The pair remained friends over the years. They went to the Vanity Fair Oscar party together in 2018, and Novak appeared in her show The Mindy Project.

Kaling posted a video of her and Novak on the way to the party, telling fans, “Happy Oscars everyone! I’m in the car on the way to one of several parties tonight with my good friend.”

Kristen Stewart and Robert Pattinson Promoted Twilight Together After She Was Caught Cheating on Him

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Fotonoticias/FilmMagic
Fotonoticias/FilmMagic

Kristen Stewart and Robert Pattinson played lovers in the Twilight franchise. They split up in 2012 after the actress was photographed cheating on him with director Rupert Sanders. Stewart and Pattinson still had to promote The Twilight Saga: Breaking Dawn Part 2 after they broke up.

When Pattison was asked by a reporter in 2018 who his favorite “boss-lady damsel that you’ve ever had the pleasure of working with” was, Stewart was not on his list. He named several women before the reporter mentioned Stewart and Pattinson said awkwardly, “Kristen Stewart as well, yeah, yeah yeah,” before quickly adding, “Catherine Hardwicke, too. She’s great.” Ouch!

Chad Michael Murray and Sophia Bush Married and Divorced While Working on One Tree Hill

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Gregg DeGuire/WireImage
Gregg DeGuire/WireImage

Sophia Bush and Chad Michael Murray met while filming One Tree Hill. They wed in 2005 but separated just a few months into their marriage. Despite what must have been extremely awkward, the pair worked together on the program for another seven years. Bush later went on to date OTH costar James Lafferty from 2008 to 2009.

Bush later said of her marriage to Murray on Watch What Happens Live in 2014: “We were two stupid kids who had no business being in a relationship in the first place. To all the other co-stars who’ve worked it out, more power to you.”

Blake Lively and Penn Badgley Didn’t Tell the Gossip Girl Cast They Were No Longer Dating

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Jamie McCarthy/WireImage
Jamie McCarthy/WireImage

Blake Lively and Penn Badgley played love interests Serena and Dan on Gossip Girl, and they also dated in real life. After they broke up, they had to continue their romantic storyline on the popular show but decided to keep their split a secret. “They kept the breakup hidden from the crew, which you could never do now,” co-producer and writer Joshua Safran told Vanity Fair in 2017.

“I don’t even know how they did it. They kept it from everybody which is a testament to how good they are as actors. Because they did not want their personal drama to relate to the show.”

Gossip Girl Co-Stars Jessica Szohr and Ed Westwick Kept Working Together Post-Split

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Frazer Harrison/Getty Images
Frazer Harrison/Getty Images

Gossip Girl costars Ed Westwick and Jessica Szohr started dating while filming the third season of the show in in 2008. They stayed together for a couple of years and split in 2010. They still worked together for a couple of years before the program ended in 2012. In 2017, Szohr spoke out when Westwick was accused of attacking several women.

She told Cosmopolitan: “It’s a difficult subject right now for anyone that’s involved on either side…I have known Ed for years and know how lovely he is and don’t think he would ever put someone in a position like that.”

Adam Brody and Rachel Bilson Put Their Differences Aside to Finish Filming The O.C.

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Chris Polk/FilmMagic
Chris Polk/FilmMagic

Rachel Bilson and Adam Brody starred together on The O.C. and dated for three years. They broke up in 2006; however, they continued to work together after the show ended one year later. Brody later married Leighton Meester and during a Reddit AMA in 2014 he talked about kissing Bilson.

“One of the all time greats!” the actor said of his ex-girlfriend, proving that there was no hard feelings between the two of them. He also joked he was in “constant psychic communication” with all of his former O.C. cast mates. Bilson went on to date Hayden Christensen.

Nikki Reed and Paul McDonald Collaborated on an Album After They Divorced

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by Taylor Hill/WireImage
by Taylor Hill/WireImage

Actress Nikki Reed met singer and American Idol contestant Paul McDonald in 2011. They got engaged and wed later that year. They split in 2014 and finalized their divorce the following year. Despite their break up, they finished working on an album together, I’m Not Falling, which they started before they tied the knot.

Reed later married actor Ian Somerhalder, and they had a daughter in 2017. That same year, McDonald started dating actress-singer Emily Kinney. The couple started their own band called The Sweetheart Deal.

Diane Keaton and Al Pacino Dated on and off for Two Decades

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Ron Galella, Ltd./WireImage
Ron Galella, Ltd./WireImage

Diane Keaton and Al Pacino had an on-again-off-again relationship with each other while filming The Godfather trilogy. They dated for 20 years. Keaton told People magazine in 2017 that she was head over heels in love with Pacino once they started dating.

“I was mad for him. Charming, hilarious, a nonstop talker. There was an aspect of him that was like a lost orphan, like this kind of crazy idiot savant. And oh, gorgeous!” she said. Then she gave him an ultimatum when he didn’t want to get married. “I worked hard on that one. I went about it in not a perfect way,” Keaton admitted.