18 Celebrity Ex-Couples Who Had To Work Together AFTER They Broke Up

Ever had a crush on a coworker? Of course, you have, you’re human. However, actually getting involved with a coworker can be quite tricky. Do you have to tell everyone? Will other coworkers treat you differently? What happens if it goes south?

When an inter-office relationship ends and the estranged parties have to keep working together, it can get ugly. When it happens to celebrities, they still look beautiful, but there’s no doubt that it’s difficult under the surface. These celebs dated co-stars, broke up, kept working together, and lived to tell the tale… as for me, I’d rather not run into an ex at the water cooler.

Kourtney Kardashian and Scott Disick

Tbh, I didn’t immediately think of the eldest Kardashian sister and Lord Disick when considering ex-couples who worked together after breaking up. Although I regard them as one of the more successful on-again, off-again celebrity couples, it’s easy to forget that starring in Keeping Up with the Kardashians is a job. After all, it’s reality television — isn’t that supposed to mean it’s just an on-camera representation of their real lives, which shouldn’t require any sort of acting of “work”? But I guess it’s where they get their paychecks, so it counts.

See them together in: Keeping Up with the Kardashians

Cameron Diaz and Justin Timberlake

Although when we first picture Justin Timberlake with a blonde in the days of our childhood/adolescence, Britney Spears is the first bombshell to come to mind, JT actually spent four years dating Cameron Diaz, after meeting at the Nickelodeon Kids’ Choice Awards in 2003. The former couple didn’t actually have to work together until four years after the split when they co-starred in Bad Teacher. Though the on-screen characters aren’t meant for one another, either, they did have to film a rather awkward sex scene together, which surely made for some great on-set banter.

See them together in: Bad Teacher

Jennifer Lawrence and Nicholas Hoult

Considering that the relationship between J-Law and beau Nicholas Hoult was never anything more than a business deal, IMO — and it makes sense: they were up-and-comers starring in a movie together who broke up after the movie, got back together for the second movie, and broke up again after that, which all drummed up great interest in X-Men — the fact that they had to work together for additional movies after the split is nothing to get bent out of shape about. It was probably in their contract all along!

See them together in: X-Men: First Class, X-Men: Days of Future Past, X-Men: Apocalypse, X-Men: Dark Phoenix

Sarah Silverman and Jimmy Kimmel

Though one of comedy’s funniest couples, Sarah Silverman and Jimmy Kimmel weren’t built to last as long as their laughs. The hilarious duo dated for approximately seven years after Kimmel’s first marriage and before his second one. Ever since their breakup in 2009, the two have had an extremely amicable relationship, appearing together in comedy sketches on Kimmel’s show more than once, even discussing stereotypically awkward topics such as Sarah’s latest boyfriend and Kimmel’s children and his ex- and current wife.

See them together in: Sarah’s appearances on Kimmel’s show, most notably the “I’m F*cking Matt Damon” sketch

Kristen Stewart and Robert Pattinson

Talk about a messy breakup situation. Not only did Kristen Stewart and Robert Pattinson break up while filming the final installment in the Twilight franchise, they broke up because Kristen was caught cheating on Robert with the married director of the other movie she was working on. Once filming finally ended, the duo still had to endure months of an international press tour promoting the movie.

See them together in: Twilight, The Twilight Saga: New Moon, The Twilight Saga: Eclipse, The Twilight Saga: Breaking Dawn Parts 1 and 2

Blake Lively and Penn Badgley

Before Blake Lively was one-half of a Hollywood power couple with Ryan Reynolds, she dated costar bae, Penn Badgley. The beautiful couple broke up while continuing to play on-screen lovers (also sometimes half-siblings), traipsing around Manhattan using their parents’ money and following their own rules. Supposedly this in and of itself caused the split: acting like they were in love on screen was enough to make them fall out of love off-camera — which they kept a secret from fellow cast members. Although the real-life version didn’t last, the made-for-TV-audiences one survived the entire series.

See them together in: Gossip Girl

Chad Michael Murray and Sophia Bush

Another beautiful on-screen couple portraying high schoolers students completely engrossed in young love. Chad Michael Murray and Sophia Bush actually tied the knot IRL, though it was a short-lived five months of matrimony for the not-even-25-year-olds. After the split, they remained costars for four years until Chad Michael Murray left the show. Characters Brooke Davis and Lucas Scott don’t end up together either, but many blame that on the actors’ insistence after the divorce. What a bummer.

See them together in: One Tree Hill

Jennifer Lopez and Marc Anthony

Jennifer Lopez and Marc Anthony are another married couple who were still in the midst of working together when they split up. The duo, who have two children, not only continued to film their reality competition TV show (which lasted for all of one season) after they had already filed for their divorce, but they’ve also made appearances on stage together, proving that just because they can’t stay married doesn’t mean they can’t still harmonize.

See them together in: Q’Viva! The Chosen, 2016 Latin Grammys, 2016 performance at Radio City Music Hall, 2017 concert in Dominican Republic

Charlie Sheen and Denise Richards

Charlie Sheen and Denise Richards were married in 1992 after working together on Loaded Weapon 1. Richards was pregnant with the couple’s second child when she filed for divorce in 2005. Richards and Sheen have been through dramatic restraining orders and custody battles — Richards even took temporary custody of the twin boys Sheen fathered with his third wife, Brooke Mueller, due to concerns regarding drug use by Sheen and Mueller — but they managed to make appearances in each other’s movies since nonetheless.

See them together in: Madea’s Witness Protection, Anger Management

Gwen Stefani and Tony Kanal

Ironically, No Doubt may never have risen to popularity and Gwen Stefani might not be the music mogul she is now if she had never dated and broken up with Tony Kanal yet continued to work with him. The singer and bassist of No Doubt had already produced two albums before they split up and wrote multiple songs about the breakup for Tragic Kingdom, the band’s breakout album. No Doubt continued to produce albums, with Stefani and Kanal working alongside one another.

Hear them in: No Doubt’s albums

Ben Affleck and Gwyneth Paltrow

The set of Shakespeare in Love became “Affleck and Paltrow in Love” when the couple met while filming in 1992 and proceeded to date on and off, including a stint from 1997-2000 after Paltrow’s relationship with Brad Pitt. Even after their breakup, Affleck convinced Paltrow to play opposite him in romantic comedy Bounce, which was actually more of a flop than a bounce. Each star — Paltrow, Pitt, and Affleck — have since been married to a different star and divorced. Perhaps one of the guys would have been better off with her all along?

See them together in: Bounce

Rachel Bilson and Adam Brody

The California sun had Summer Roberts and Seth Cohen falling in love on television and it must have leaked into their real lives a little. Rachel Bilson and Adam Brody dated for three years during the making of The O.C., breaking it off with a year of filming left — which, ironically, ended with the marriage of their two characters. Adam is now married to Gossip Girl star Leighton Meester, and though Rachel was briefly engaged to Hayden Christensen, with whom she has a child, she’s currently single.

See them together in: The O.C.

50 Cent and Vivica A. Fox

Rapper and actor 50 Cent and actress Vivica A. Fox dated for two years and became one of those he-said, she-said couples after the breakup, flinging insults at one another with neither willing to accept responsibility for the split. Fitting that their reunion two years later featured Ms. Fox as an angry ex-girlfriend in one of 50 Cent’s music videos. In 2016, more than a decade after the couple broke up, they rekindled their feud after Vivica A. Fox made comments about 50 Cent being gay and 50 Cent took to Instagram to defend himself by attacking her.

See them together in: 50 Cent’s “Do You Think About Me” music video

Avril Lavigne and Chad Kroeger

The Sk8er Boi punk-ess and Nickelback frontman first got together for purely professional and artistic reasons — to write songs for Avril’s upcoming album. The two ended up creating more than music together and ended up married for two years before divorcing in 2015. Even after their split, they shared with fans that they were still writing music together. Though Avril has been laying low after her diagnosis of Lymes disease, she made her first appearance on stage in three years at a Nickelback show.

See them together in: Avril’s cameo in “Rockstar” at a 2017 Nickelback show in LA

Katie Holmes and Joshua Jackson

Are romances grown from high school television dramas doomed to fail? It certainly seems that way. Although Joey Potter and Pacey Witter end up together on The WB, the real life couple got together and split up while the show was still going. Holmes, who was still a teen when she started dating her costar, admits that Jackson was her first love, even though it didn’t last as long as their on-screen relationship did.

See them together in: Dawson’s Creek

Nina Dobrev and Ian Somerhalder

Although not vampires IRL, the on-screen romance between Damon Salvatore and Elena Gilbert was very real for Ian Somerhalder and Nina Dobrev for a time. The real-life version of the couple was private about their three-year relationship, yet public enough to make fans of the show swoon. They remained co-stars for two years after breaking up in 2013, even receiving the People’s Choice Award for “Best Chemistry” in 2014. Nina did opt out of the show a bit early, but the exes remain friends, and Dobrev is also friendly with Somerhalder’s wife, Nikki Reed.

See them together in: The Vampire Diaries

Kaley Cuoco and Johnny Galecki

Although Leonard Hofstadter and Penny got married (twice!) on television, Johnny Galecki and Kaley Cuoco didn’t quite make it to a Vegas chapel or down the aisle. The couple dated for nearly two years in private, keeping it a secret from costars and the public, and though they broke up in 2010, they continue to work together — and play an on-screen couple — on The Big Bang Theory seven years later. Talk about staying friends with an ex!

See them together in: The Big Bang Theory

Elizabeth Taylor and Richard Burton

Such a timeless yet whirlwind of a romance! Elizabeth Taylor and Richard Burton were on-again, off-again to make anyone’s head spin. The couple first met in the 1960s on set of Cleopatra, when both of them were married to other people — and the drama never stopped. The fiery duo was married twice and divorced twice, splitting for the last time in 1976. Seven years later, they acted opposite one another in Private Lives; Burton passed away just one year later. May they both rest in peace.

See them together in: Private Lives

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