Celebrities Who Dated Their Friends' Exes: Taylor Swift, Selena Gomez

It’s hard enough to see your ex move on with someone new, but it’s even worse when you’re famous … and they go on to date one of your friends! That’s exactly what happened to Taylor Swift, Selena Gomez, Gigi Hadid and more celebrities.

Despite the awkward circumstances, some A-listers still managed to come out on top and even made something positive out of their unfortunate heartbreak — just think of all the breakup anthems we got out of it! Take Joe Jonas, for example. The “Sucker” artist dated Taylor in 2008 and then found love with the “London Boy” singer’s BFF Gigi in 2015.

Taylor detailed her relationship with Joe in her hit song “Forever & Always,” which peaked at No. 44 on the Billboard charts in 2008. The couple’s split was particularly tough, as Taylor detailed the not-so-nice way Joe dumped her to Ellen DeGeneres in November of that year.

“When I find that person that is right for me, he’ll be wonderful and when I look at that person, I’m not even gonna be able to remember the boy who broke up with me over the phone in 25 seconds when I was 18,” she explained at the time. Taylor has been dating boyfriend Joe Alwyn for nearly four years, and it seems like they are happier than ever. Plus, she’s still close with Gigi and Joe to this day!

Moreover, the Jonas Brothers member is happily married to wife Sophie Turner. The sweet pair welcomed daughter Willa in July 2020. For Gigi’s part, she and off-again, on-again boyfriend Zayn Malik are very much back together and raising daughter Khai, who was born in September 2020.

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Of course, Taylor, Gigi and Joe are hardly the first love triangle in Hollywood. Nina Dobrev and Ian Somerhalder used to be an item after they met while working on The Vampire Diaries in 2009. The actor moved on with Nikki Reed — who is friends with Nina — but luckily, the trio laughs about the situation these days.

“I think they have a beautiful baby, and they are happy, and so am I,” Nina said during an appearance on Watch What Happens Live With Andy Cohen in January 2019. “What’s bad about that? I don’t see any problem with that.”

If these celebrities can be cordial with their pals and exes, then clearly, so can everyone! Scroll through the gallery below to see all of the celebrities who dated their friends’ exes.

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Drew-Barrymore / Fabrizio Moretti / Kristen Wiig

Drew Barrymore dated Fabrizio Moretti for five years, but they broke up in 2007. The drummer then moved on with Drew’s friend Kristen Wiig in 2011. “It all seems wacky and incestuous, but that’s kind of how it works,” the mom of two explained to Allure about the love triangle in 2012. “It seems fitting that they would find each other. I was like, ‘Right, of course, that makes perfect sense.’”

Jennifer Aniston / Adam Durit / Courteney Cox

Jennifer Aniston and Courteney Cox have more than a hit TV show in common — they also both dated Counting Crows frontman Adam Duritz. Jen dated the musician in 1995 before he moved on with the mom of one. However, Jen and Adam didn’t seem to have a serious relationship and he admitted, “We never even slept together.” But his relationship with Courteney was much more intense since he wrote the song “Monkey” about her, and she even made a cameo in the band’s music video for “A Long December.”

Lance Armstrong / Kate Hudson / Owen Wilson

Same guys, different girl. Kate Hudson dated Owen after meeting on the set of the 2006 film You, Me & Dupree. The former flames broke up in 2007, but they briefly got back together in 2008 before they ended things for good. Later that same year, the blonde beauty dated Lance for several months. Awkward.

Nina Dobrev / Nikki Reed / Ian Somerhalder

Nina and Ian met on the set of The Vampire Diaries and dated for more than three years. In 2014, the actor moved on with their mutual friend Nikki. Now, Ian and Nikki are happily married and share one child together, and the three of them are actually really close. “Can’t believe how time flies. Farewell dinner with team Somereed!” Nina captioned a photo of the three of them together on Instagram. “So good catching up with these goofballs. All [love].”

Selena Gomez / Taylor Swift / Taylor Lautner

Don’t worry, Taylor and Selena are doing just fine even though they both dated the same guy — Taylor Lautner. The Twilight stud and the brunette beauty had a fling in early 2009, and later that same year, Taylor dated the “Shake It Off” songstress for a few short months. The former flames even starred in the movie Valentine’s Day together.

Taylor Swift / Katy Perry / John Mayer

Taylor and Katy Perry have since buried the hatchet, but back in the day, the pop stars both dated John Mayer. The handsome hunk dated Taylor in 2009, while Katy dated the “Clarity” singer on and off for years until they split for good in 2015. Taylor even wrote “Dear John” about her relationship with … you guessed it, John. Meanwhile, in 2017, John admitted his song “Still Feel Like Your Man” was about the brunette babe.

Taylor Swift / Calvin Harris / Ellie Goulding

That’s what friends are for? Ellie Goulding and Calvin Harris reportedly dated in 2013, but the U.K. beauty was apparently the one to set up Taylor with her ex. “I did play matchmaker, that’s true,” she told The Sun in June 2015. “Calvin is a really great mate, and he’s so fantastic, and Taylor is such a cool person who I love. I thought, ‘They’re both really awesome and both really tall, they’ll be brilliant together.’” Unfortunately, Calvin and Tay called it quits in 2016 after dating for over a year.