Kiss of Death: Celebs Who Had to Work With Their Exes

Rough, tear-jerking breakups – we’ve all been through them, or at least know someone who has. This is a sensitive time in any person’s life, celebrities included. Most of us would just want to sit at home, watch sad movies and eat ice cream. But life goes on, even if we don’t want it to. What would you do if you had to see your ex every day at work? Or, worse, what if you had to kiss them, and pretend to still be together?
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That is a reality for many actors, and truly is one of the only cases in which we really feel bad for them! Get ready to read some juicy stories about celebs who had to continue working alongside their former lovers.

Joking Aside

Breakups come in all shapes and sizes. Dating someone for four years and then ending the relationship can leave someone with a lot of hard feelings. But get this, after maintaining an almost five-year relationship Cameron Diaz and Justin Timberlake broke it off in 2007. By a twist of fate (and by that we mean casting directors) the two found themselves staring the 2011 movie “Bad Teacher” together.

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While in character, Cameron had to hit on Justin. According to her, this was actually a great experience as the two often joke and laugh together. Whether you believe her or not, that’s up to you.

Together After the Divorce?

JLo, AKA Jenny from the block, is one of the biggest stars out there. It made sense when she started dating singer-songwriter, Marc Anthony. Sadly, after being together for seven lucky years, the two split up.

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They actually didn’t let that stop them from electively working together on Lopez’s Spanish record as well as on a TV competition show titled “Q’Viva!”Just like many others on this list, Jen likes to claim that working together was great and that it has actually made their relationship better. You decide.

Seeing Your Ex Everyday

Back in the early 2000s, there was one show everyone was obsessed with, the younger kids might not remember, but before people couldn’t stop talking about “Game of Thrones” there was “Lost.”

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Co-starts Dominic Monaghan and Evangeline Lilly hit it off and soon enough the two were dating in real life, while their characters were involved as well. It seemed that the two stopped seeing each other in 2007, but they couldn’t actually stop seeing each other since they literally had to go to work and see their ex every day till the year 2010.

Incredibly Bizarre

These two actors didn’t confirm the rumors about them being together for years. Their chemistry was obvious as Betty (Lili Reinhart) and Jughead (Cole Sprouse) on “Riverdale.” Fans soon suspected they were madly in love while journalists knew their relationship was an open secret.

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Wistfully, after three secretive, years, Cole finally confirmed they broke up in May of 2020. A few months later, the two were back on the set of their teen show. Awkward! Lili has spoken out saying that being an actor is incredibly bizarre and that you can find yourself having to deal with things no one else has to deal with.

Nobody Knew

What is it about the number three? It seems that many couples choose to part ways after they reach the three-year milestone. Before Blake Lively married Ryan Reynolds she dated her “Gossip Girl” co-star, Penn Badgley.

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But get this, not only did the two try and keep their relationship secret, they tried to do the same with the breakup, and it worked! The show’s director and crew shared with us they had no idea the two were no longer dating. How did they pull that off? With their acting skills, probably.

A Tragic Affair

Actors who work on the same TV show or movie can’t always help it if they have to work together after they are no longer in love. With musicians and bands, it’s not that different. “No Doubt” lead singer, Gwen Stefani dated the band’s bassist, Tony Kanal.

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They broke up in 1994, but that wasn’t the end of the band, which continued releasing albums up until 2012 and has never officially called it quits. Why did they decide to continue working together? Maybe they didn’t want to lose both a lover and their income. They even made some money writing the song “Tragic Kingdom” about their past affair.

Childhood Trauma

This story has somewhat of a circular structure: Ben Affleck and Gwyneth Paltrow met on the set of one movie, and then had to meet again, after they had already broken up, in order to promote another movie.

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They first fell in love in 1998’s “Shakespeare in Love.” and by the time their 2000 flick “Bounce” came out in 2000 they were already apart. Gwyneth was quoted saying that Ben isn’t the type of boyfriend you marry, but the one you date to heal childhood trauma. Is that a good thing or a bad one? Honestly, we don’t know.

A Cheating Scandal

The romance between that hot, male vampire and a young teenage girl is a classic and will always be. That’s why fans went crazy when the movies for the book series “Twilight” finally came out. Co-starts Kristen Stewart and Robert Pattinson immediately fell head over heels for each other.

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We all know what happened next: Kristen was caught cheating with a director and Robert was humiliated. The two awkwardly had to promote their own movie together, which is a situation none of us would want to be in.

He’s Just Not That Into You

Drew Barrymore was Hollywood’s wild child for quite some time and has been linked to many different men. Most famously she had a short-lived marriage to Tom Green. Not many remember that Drew also dated Justin Long, after meeting him on the set of “He’s Just Not That Into You.”

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The couple broke it off after a year but in 2010, they had to portray a couple once again, in “Going the Distance.” Hopefully, it wasn’t too hard for them.

More Gossip

Blake lively and Penn Badgley weren’t the only ones getting it on on the set of Gossip Girl. Ed Westwick, which many of us knew as Chuck Bass, and Jessica Szohr who played Vanessa Abrams also had a fling.

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These guys just couldn’t decide if they wanted to be together or not, as they spent three years breaking up and getting back together again. Rumor has it that they still kept it professional on set, and honestly, we’re dying for some tips.

Kiss And Tell

There’s just something about teen shows, it is impossible to find one without an off-screen love story! In “Teen Wolf” it was actors Crystal Reed and Daniel Sharman who had a spark and pursued a romantic relationship.

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But even after the two broke up, their characters still stayed together and Reed told new sources that they even had to shoot a make-out scene. Well… at least they didn’t have to rehearse it much?

A Musical Drama

These two might be the youngest ones on our list! Olivia Rodrigo and Joshua Bassett from Disney Plus’ “High School Musical: The Musical: The Series” are rumored to have started dating sometime during the show’s shooting. It seems that just as secretively as they have started dating, they have also ended the relationship, but still had to shoot the show’s second season together.

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In a twist, despite not having ever confirmed their relationship, Olivia has written an entire album about the breakup! Imagine having to shoot a show with someone after having written an entire album about how they wronged you, Awkward!

A Romantic Tragedy

Sarah Paulson and Holland Taylor have been going strong since 2015, but before the two found each other, Paulson dated Cherry Jones. The two award-winning actresses participated in the 2005’s Swimmers” together. We imagine seeing your partner every day at work is great fun when the relationship is still going strong.

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But, after you get your heart broken, or break someone else’s heart, well… that’s a whole other story. The two had to work together in 2011, two years after they decided to part ways, in a romantic comedy named “New Year’s Eve.”

Doctors With Broken Hearts

Before we had “Grey’s Anatony” we had “House.” The show was groundbreaking in many ways, but when it came to co-stars getting together and then splitting up, it was just like any other show. Jennifer Morrison and Jesse Spencer who played doctors Allison Cameron Robert Chase almost got married!

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They canceled their engagement in 2007, while in 2008, during the show’s 5th season their characters tied the knot. Morrison shared that they only kissed while the camera was on, and did not rehearse any of their kisses before. Makes sense.

Two On-Set Romances

While portraying the iconic Rory in “Gilmore Girls” Alexis Bledel dated not one of two of her co-stars (not at the same time though! That would have been a whole other drama.) She had a four-year relationship with Milo Ventimiglia who played bad-boy Jess.

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Luckily for both, by the time they broke up in 2006 Ventimiglia’s character stopped being a show regular. In 2016, ten years later, the two had to reunite for the show’s final season. We hope they didn’t carry any grudges.

The Green-Eyed Monster

For four seasons between 2003 to 2007, we all tuned in to watch what was going on with Seth, Ryan, Marissa, and Summer. Seth and Summer’s chemistry was off the charts and soon actors Adam Brody and Rachal Bilson developed a passionate relationship themselves.

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The two separated in 2006, and Bilson admitted later she was jealous every time Brody had to kiss someone else on set. Funnily enough, Brody ended up marrying another huge teen show actor, Leighton Meester who depicted  Blair on “Gossip Girl.”

Obvious Tension

Acting alongside your ex is one thing, but having to be given directions by them is a whole other thing. That’s what happened to Charlize Theron who had to complete the movie “The Last Face”, directed by  Sean Penn after the two broke off their engagement.

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They spent 18 months together and had to promote their movie right after the spilt. They tried to pretend everything was ok between them, but new outlets said that wasn’t the case, claiming there was obvious tension between the two.

A Traumatic Divorce

Five months after getting married costars Chad Michael Murray and Sophia Bush filed for divorce. They tried to act cool on the “One Tree Hill” set, where they played couple Brooke Davis and Lucas Scott.

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Over a decade later Bush admitted the whole event was traumatic and that she felt pressure to marry Murray, especially from the producers who told her she’s the only one who could get Chad to show up to set on time. He denied all of her claims about being a difficult actor. In 2015 he married actress Sarah Roemer and started a family with her.

A Family Affair

If there’s one thing we’ve gathered from this list is that playing lovers on-screen is a recipe for real-life romance. Michael C. Hall And Jennifer Carpenter had a different story, they portrayed a brother and sister and married secretly. Fans had to get used to them not being siblings but a husband and wife.

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They had to continue to work on the hit show “Dexter” for two years after they got divorced. Carpenter shared that even after they broke up, they had love and respect for each other and for the show. Still, it’s gotta be painful to see your ex-husband every day, at least they played siblings!

Bad Boyrfriend

Felicity followed the title character’s journey in college. In the show, she follows her high school crush, Ben, all the way to his chosen school in New York. Actors Keri Russell and Scott Speedman had a good connection outside of the show as well.

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The romance didn’t last and Speedman also admitted later he wasn’t a good boyfriend to Keri. Luckily it seems they managed to get past it, and the two reunited for Jimmy Kimmel and dished out about that time they were young and dating each others.

In and Out of Love

You have to admit that you’d expect a popular show like “Friends” that lasted for so many seasons to have more off-screen relationships, but, well, somehow it didn’t. The cast of the show made a pact to remain, well friends!

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But one guest star did have an affair with Jenifer Aniston before he was ever on the show: Tate Donovon. He came on to play Joshua and later admitted it was incredibly uncomfortable and painful for the two to act as if they were just falling in love when in actuality they were falling out of it.

Fool Me Twice…

Milo Ventimiglia must be a charmer, as his romance with co-star Alexis Bledel on “Gilmore Girls” wasn’t his only one. While portraying the role of Peter Petrelli in the tv show “Heroes,” Milo started dating Hayden Panettiere. They spent two years together despite their 12-year age gap.

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We guess this time Milo learned his lesson, he said he would never want to be in such a publicized relationship ever again. As for Panettiere, she was linked to Brian Hickerson for a couple of years and also has a daughter from a previous marriage.

Hard to Work Together

When you form a band with someone and spend almost all of your time on tour with them, it only makes sense that you’d end up falling in love. Jack and Meg of “The White Stripes” were together from 1996 to 2000.

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Despite the fact they separated and got a divorce in 2000 they continued performing together for ten more years! They broke up in 2011, and years later Jack revealed that Meg was very hard to work with.

Teen Drama

“Dawson’s Creek” was all the rage in 1998. It was one of the first shows that portrayed teenagers as having complicated inner lives, just like adults do. Complications were not just a part of the script though, but also of the actors’ real lives.

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Katie Holmes and Joshua Jackson fell in love on set but broke up before the show ended. Unfortunately, two years after their breakup, their characters got together. They claim it was fine by them, but could you envision having to kiss an ex after you’ve just gotten over them?

The Kissing Booth

Netflix’s high-school movie “The Kissing Booth” broke records when it first came out in 2017, so it’s only natural two sequels were made. Stars Joey King and Jacob Elordi fell in love in 2017 but ended up splitting in 2018.

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They had to shoot two more movies together, post-break-up, with their characters, head over heels in love. King told interviewers that she knows people want to know everything about what it’s like to pretend to be in love with your ex, but has refused to give away any revealing details, saying she does everything she can to stay professional.

Bella’s Secret

Once you’ve called it off with someone, you don’t expect to see them in their underwear anytime soon, but that’s exactly what happened to Bella Hadid and The Weeknd. The two had a volatile on-and-off relationship that ended in 2016.

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One month post break up the two met on the Victoria’s Secret Fashion Show runway where The Weeknd was performing and Hadid was modeling the newest collection. The two acted like the professionals they both are, but could you imagine them fighting on the runway? That would have been one hell of a show.

Mama Mia!

Amanda Seyfried and Dominic Cooper met on the set of the musical film “Mama Mia.” While some set romances are short and end as fast as they started, Seyfried and Cooper were actually together for three years.

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When it was time to film the sequel “Mamma Mia! Here We Go Again” the two were already broken up. Dominic said it’s important to be delicate and considerate in these types of situations, but refused to say anything bad about the experience of acting alongside an ex.

Disappointed and Heartbroken

What is it with people who play siblings on TV? Just like in “Dexter,” Dave Annable and Emily VanCamp fell in love on the set of “Brothers & Sisters” while playing, well… brother and sister.

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The two had an insane connection, not exactly the love you would have between two siblings. Sadly the two stopped seeing each other in 2008 but kept on working together until 2011. Rumors have it that things did not end well between the two, VanCamp has alluded to being disappointed and heartbroken.

Divorcing The Same Person Twice

Marrying someone once and divorcing them might be an honest mistake, but twice? Hollywood Royalty Elizabeth Taylor and Richard Burton tied the knot for the first time in 1964. They filed for divorce in 1974, but married again in 1975, only to get yet another divorce in 1976.

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In 1983 they agreed to play in the movie “Private Lives” together. The movie failed, and many pointed out both actors looked as if they were using illegal substances. Could this have been their way of coping with the peculiar situation? We’ll never know.

Refusing to Settle Down

Diane Keaton and Al Pacino were together for almost two decades, from 1972 to 1989. They had a rocky relationship and broke up and got back together a lot during these years.

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Still, they starred in “The Godfather” trilogy together. It is had been said that they ended the relationship because of Pacino’s refusal to get married. In 2019 Kraton told people magazines she’s happy she never got married.

Put In the Work

If anyone knows how to put in the work, it must be Dwayne “The Rock” Johnson. He married Dany Garcia in 1997 and the two managed to stay married until 2008. One year prior to their divorce they started a production company together.

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Even after splitting, they decided to keep the company and work alongside each other. How did they do it? Johnson is one of the few celebrities that actually admitted that working with an ex is hard. He stated therapy has helped him get through it.

Keying His Car

Celebrities seem to like to claim that all of their breakups ended on a good note with no hard feelings, but we know that’s not actually the case. Actress Naya Rivera took her on-set breakup pretty hard, as she supposedly keyed the car of her ex and glee cast member Mark Salling.

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Imagine having to pretend to be in love with someone who purposefully ruined your car! Writers soon made their characters, Santana and Puck, part ways as well.

BTW, I’m Gay

Sara Gilbert and Johnny Galecki played couple David and Darlene in the 80’s classic “Roseanne.” They dated in real life but their romance did not work out and in 2013, Sara confessed she realized she was attracted to women while dating Johnny.

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Galecki was sweet about it, according to Gilbert,  and remained supportive throughout the years. The two reunited for the show’s reboot in 2018 with no hard feelings between them.

The Dating Diaries

Nina Dobrev and Ian Somerhalder met on the set of “The Vampire Diaries” while portraying a human girl and a vampire who fall in love. Just like Kristen Stewart and Robert Pattinson on the set of “Twilight”, Ian and Nina started developing feelings for each other.

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They were together for three whole years. In 2015, Ian stopped appearing on “The Vampire Diaries,” and many believe it was their breakup that made him leave the successful show.

Teacher’s Pet

Lea Michele and Matthew Morrison didn’t actually meet on the set of Ryan Murphy’s “Glee” but knew each other for years before the show’s inception. They played teacher and student and on the show, but Lea revealed they dated in real life before having been reunited on set.

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While they didn’t have to pretend to be in love on the show, they did have to be close to each other, and Lea’s character had a crush on Matthew. Tricky.

Office Romance

Before comedian Mindy Kaling got her own show, “The Mindy Project,” she portrayed Kelly in 2004’s “The Office.” That’s where she met B.J. Novak who played Ryan Howard. Just like their characters, Mindy and BJ had a volatile real-life relationship.

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We assume it was hard for them to be on set during the times they were off, but it seems they have pushed through it, as they are still close friends. Mindy even made BJ the godfather of her daughter. How sweet.

A Brief Affair

“The Transformers” is a long-lasting franchise that is loved by many and has been a part of our lives for decades. The 2007 movie by the same name gave birth to a brief affair between model Megan Fox and actor Shia LaBeouf.

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They ended their relationship pretty quickly, but the show, or in this case, the movie, must go on. They had to shoot yet another transformers movie in 2009. LaBeouf has later admitted he finds it hard to understand how people can separate work and life so easily. Finally, someone who’s being honest!

An Intimate Scene

Actors Kyle MacLachlan and Laura Dern, who famously starred in David Lynch’s “Blue Velvet” were together for three years and were even engaged to be married.

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But, alas, the two broke up. Two decades later, they had to shoot an intimate scene together on the set of Lynch’s “Twin Peaks: The Return.” MacLachlan confessed it was terribly weird to be reenacting such a private act, 25 years later, for the whole world to see.

It’s Complicated

For as long as movie and TV sets existed, they were people falling in love while working on them. And while we wouldn’t really say that “Alias” was romantic, we guess it was romantic enough for Jennifer Garner and Michael Vartan. They got involved pretty soon after Garner divorced Scott Foley, her “Felicity” co-star.

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If that’s not complicated enough, Michael and Jenifer had to continue working on “Alias” together for two years after they broke up. Both actors went on to marry and (divorce) other people, so we guess it’s all water under the bridge now.

The End of an Era

Let’s face it, we don’t usually expect Hollywood couples to last. Call us cynical, but it’s gotten hard to have faith that celebrities will stay together till death do them part. But, Liev Schreiber and Naomi Watts were a pair we really rooed for.

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Unfortunately, after making it work for over a decade, they split in 2016. That didn’t stop them from making a movie together, “Chuck,” that same year. Schreiber said that acting alongside his ex was a treat, and we’re not sure if he was being sarcastic or not.

“Conflicting Schedules”

Picture this: the year is 2011, the place is the set of the film “X-Men: First Class.” Nicholas Hoult of “Skins” fame and Jennifer Lawrence, who needs no introduction, met and fell in love.

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They had a good run, dating for over two years, but had to work on another ex-man movie “X-Men: Apocalypse.” Their official reason for splitting up was conflicting schedules, which is bizarre in our opinion as they working on the same movie!

Keeping Up with The Ex

In this day and age, it’s impossible not to talk about one Kardashian or the other. This family is everywhere, a lot of it thanks to the reality show “Keeping Up with The Kardashians,” which follows their luxurious lives.

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If you watched it, you know that Kourtney Kardashian and  Scott Disick dated on and off for ten whole years! Although they decide to keep the relationship platonic from 2015 and on. Disick still appears on the show, we guess it’s good for the ratings.

Two On-Set Breakups

Hit teen show Riverdale gave us the inception and the demise of Cole and Lili’s relationship, but not many know they weren’t the only couple on set. Camila Mendes, who you probably know as Veronica Lodge dated Charles Melton AKA Reggie Mantle on “Riverdale.”

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By December 0f 2019 the two were no longer together, but in 2020, both had to continue shooting with each other. Hopefully, they asked Lili and Cole for tips.

A Secretive Affair

“The Big Bang Theory” isn’t the show we excepted to produce simmering off-set relationships, as it mostly deals with how Leonard and Sheldon aren’t that great at human relations.

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Nonetheless, Johnny Galecki and Kaley Cuoco hit it off and secretly spent two beautiful years together in the late 2000s. The show went on till 2019. Later, Kaley stated that she hated having to hide every aspect of her relationship and we’re assuming that’s what tore the two apart.

An Uncomfortable Goodbye

Today, “Gossip Girl” star is married to “The O.C” star Adam Brody, but before the two met she had a hot, long-lasting fling with one of her “Gossip Girl” co-stars, and no, it wasn’t Ed Westwick!

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Sebastian Stan, who played Carter Baizen on the show dated Meester for two years. She has opened up in interviews saying their 2010 breakup was very hard for her, so we can only assume it was very uncomfortable to see him on set.

Calling it Quits

Before Katherine Heigl became a huge star thanks to her role on “Grey’s Anatomy” she was a part of 1999’s “Rosewell.” That’s where she met Jason Behr, and despite playing siblings on the show and the two pursued a relationship with each other.

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At one point, rumors started circulating that they were engaged. Luckily for them, they broke up just a little bit before the show wrapped up, so they didn’t have to see each other too much on set.

No Longer Friends

Before they broke up Bradley Cooper and Zoe Saldana made for a beautiful pair. They met on the set of “The Guardians of the Galaxy” and dated for a full year. Unlike others on this list, Zoe said she does not like to stay friends with exes.

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Well, she did have to meet him again, as Cooper returned to “The Guardians of the Galaxy” to voice an animated raccoon. This is indeed a very bizarre way of meeting your ex again.

Beating Around The Bush

Bush had several different affairs on the set of the teen show “One Tree Hill” alone. After finalizing her divorce from Chad Michael Murray, Sophia dated co-star Austin Nichols.

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She learned the lesson and hid this relationship for four whole years before she revealed their relationship. That’s some impressive secret dating! After six years, they broke up in 2012 but had to continue shooting the show together.

Dream Job Gone Wrong

After “One Tree Hill” was done, actress Sophia Bush landed a role in “Chicago P.D.” In 2014, her name was linked to yet another colleague, Jesse Lee Soffer. They dated for less than a year and had to continue with the show for a few more years.

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Bush finally decided to quit “Chicago P.D.” We are left to wonder if Jesse was one of the reasons as to why she decided to walk away from what she once called her “Dream job.”