A Slew of Celebs Who Dated the Same Person—And How Everyone, Uhm, Handled It

"Hearst Magazines and Yahoo may earn commission or revenue on some items through these links."

Remember when Taylor Swift stepped out for dinner with Gigi Hadid and Sophie Turner, and fans wisely remarked that she was assembling Joe Jonas's exes like Avengers? Truly, it was a deeply cathartic series of photos to gaze at instead of doing work—probably because there's simply nothing more powerful than bonding with your ex's other exes. And complaining about said ex in the process, of course.

All of that's to say that a lot of celebrities have dated the same person. And believe us when we say that you are simply not prepared for the '90s celebrity drama we dusted off while putting this together. Like, it turns out Julia Roberts lived the plot of Runaway Bride, that's all we're saying.

Shawn Mendes and Justin Bieber

Personally, I can barely recall 2018, but this was apparently when Hailey Bieber (then Hailey Baldwin) and Shawn Mendes were rumored to be dating. They even attended the Met Gala together! Hailey, obviously, moved on with Justin Bieber.

Courteney Cox and Jennifer Aniston

Correct: Counting Crows frontman Adam Duritz dated both Courteney Cox and Jennifer Aniston. Will give you a moment to process.

Adam and JenAn dated in 1995 after meeting at the Viper Room (lol), while he and Courteney dated a couple years later in 1997. Adam spoke about dating both Friends stars to Men’s Health in 2014, saying "They were nice girls and I went out with them and that was that." (We feel silly even clarifying this, but Jen and Court's relationship is beyond fine, btw!)

Taylor Swift and Demi Lovato

Kay, time to buckle up because we've reached the first of many (m-a-n-y) Jonas Brothers mentions in our journey. You probably need no reminders here, but Taylor dated Joe Jonas "Mr. Perfectly Fine" in 2008, until that infamous 27-second breakup call. Joe went on to date another songstress—and his Camp Rock co-star—Demi Lovato, circa 2010.

Taylor Swift and Sophie Turner

We're still here, stay with us. Years later, in 2019, Joe married Game of Thrones star Sophie Turner and had two children with her—but the pair very publicly split in September 2023. (In perhaps THE most iconic instance of Exes Uniting Against a Common Jonas™, Taylor and Sophie subsequently started hanging non-stop. Like, Taylor straight-up loaned Sophie an apartment to live in.)

Kieffer Sutherland and Jason Patric

PREPARE YOURSELF FOR DRAMA. Kiefer Sutherland and Julia Roberts were fully engaged in 1991, but she called things off three days before their wedding and flew to Ireland with Kiefer's close friend and The Lost Boys co-star, Jason Patric. It's like the plot of a movie. Oh wait!

No worries, though, Kieffer harbours no ill will, telling Rolling Stone in 2006, "I commend Julia for seeing how young and silly we were, even at the last minute, even as painful and as difficult as it was," he told Rolling Stone. "Thank God she saw it."

Bella Hadid and Simi Haze

Jaws truly hit the floor when The Weeknd stepped out with his ex-girlfriend Bella Hadid's best friend Simi Haze in 2022. And it looks like Bella was just as surprised as the rest of us, because she stopped following Simi on Instagram. (FYI, The Weeknd and Simi appear to still be going strong!)

Taylor Lautner and Jamie Campbell Bower

Taylor Lautner and Jamie Campbell Bower have several things in common: 1) dating Lily Collins, and 2) starring in the should-have-been-Oscar-winning Twilight SAGA.

Taylor Swift and Selena Gomez

Not done with Taylor "Bella, Where the Hell Have You Been, Loca" Lautner just yet! He and Selena Gomez reportedly dated after meeting on Ramona and Beezus in 2009, but their relationship lasted like two seconds. Meanwhile, Taylor & Taylor also dated in 2009—and she even wrote "Back to December" about him! Needless to say, this did no damage whatsoever to Tay and Sel's super-solid friendship.

Lance Armstrong and Owen Wilson

Time to take things back to the early aughts...ie. a truly messy time for celebrity relationships. Let's kick things off with Owen Wilson and Sheryl Crow, who started dating in 1999. Things didn't work out, and Sheryl started dating (and got engaged to!) Owen's good friend, Lance Armstrong. Seems like Owen was fine with it since they remained friends, but keep scrolling...

Lance Armstrong and Owen Wilson (Again)

Because once wasn't enough, after splitting from Sheryl, Lance dated yet another one of his friend's exes—specifically Kate Hudson. Lance and Kate got together shortly after Kate's split from Owen in 2008. Welp.

Nick Cannon and Nick Lachey

As a reminder, Nick Lachey and Kimberly were together in 2006 (they went on a date to see The Da Vinci Code and Nick later implied she called the paps to capture it), while Nick Cannon and Kim dated for about a year after meeting on set of Moesha, also in 2006.

Gwyneth Paltrow and Drew Barrymore

Drew Barrymore and Luke Wilson dated for three years in the mid-90s and remained good friends after breaking up—like, Luke even appeared in Charlie's Angels! Meanwhile, he and Gwyneth got together after starring in 2001's The Royal Tenenbaums. Neither relationship lasted, but you know whose did? Gwyneth and Drew's, 'cause they're planning to go on a "naked oyster" double date. ¯\_(ツ)_/¯

Chris Pine and Channing Tatum

As we know, due to their couples Halloween announcement, Channing Tatum and Zoë Kravitz are engaged/cute/hot. But before she was falling for the Magic Mike star, Zoë was dating Chris Pine (the year was 2010-ish)—who happens to be good friends with Chan. Like, they were spotted bicycling around D.C. back in 2018.

Ben Affleck and Bradley Cooper

In between Bennifer calling off their engagement in 2004 and reuniting/getting married in 2022, Bradley and J.Lo were rumored to be dating in 2011. A source told People at the time, "She does like his attention, and it makes her feel good that he seems so into her."

Zoe Saldaña and J.Lo

We already went through J.Lo and BCoop's whole thing, but he and Zoe were slightly more serious. They dated for four months in 2012, until a source told E! News, "He dumped her." But then they got back together a few months later (and attended the premiere of their movie The Words)…only to split up again in January 2013.

Zoe Saldaña and Renée Zellweger

Sry, not done with Bradley yet. He dated Renée Zellweger right before getting together with Zoe—and their relationship lasted about two years, before she called things off in 2011 Why? Per Us Weekly, Bradley was too career-focused.

Taylor Swift and Gigi Hadid

It's not just Demi and Sophie. Taylor is best friends with Joe Jonas's other A-list ex, Gigi Hadid, who she's been close to for years. (Psst: Taylor had zero problem with Gigi dating Joe when they got together—she even went on a double date with them while she was dating Calvin Harris!)

Joe Jonas and Zayn Malik

Congrats, you've made it this far and we're still not done talking about Joe Jonas. Turns out Gigi Hadid started dating Zayn Malik two weeks after she and Joe split, prompting Joe to say this out loud: "I think it’s interesting that she moved on so quickly. I mean it was definitely very quick." He also deleted a photo of himself and Zayn with Kanye West, which he'd captioned "Squad." Eek!

George Harrison and Eric Clapton

Pattie Boyd married George Harrison in the 1960s, which became super awkward when she got close to his good friend, Eric Clapton—who promptly fell in love with her. (Relatable, this kinda thing happens to me all the time too.) Pattie eventually left George and married Eric, and they all stayed good friends!

Cameron Diaz and Kate Hudson

Cameron Diaz and Kate Hudson had a rumored feud in the mid-aughts when Kate started dating Justin Timberlake right after he and Cameron split. Tea, but honestly, this is just the beginning...

Cameron Diaz and Kate Hudson (Again)

The thing is, Cameron and Kate's alleged beef escalated when Cameron started dating A-Rod after his split with Kate. In 2010, Us Weekly reported, "Kate thinks it's payback, pure and simple." Meanwhile, a friend of Cameron's said, "Cameron was actually in a serious long-term relationship with Justin. She thinks it's a joke Kate would be mad. Kate is only upset because she hates being single." Awk times!

Katy Perry and Taylor Swift

John Mayer and Taylor Swift dated for a few months, circa 2009/2010, and no one will ever forget about it, thanks to a lil' ditty called "Dear John." Then about a year later, John and Katy started dating. This doesn't seem to be the source of their "bad blood" though!

Selena Gomez and Miley Cyrus

Guess who's back? Back again? A JONAS BROTHER. (Not Kevin...or even Joe this time!)

Nick Jonas and Selena Gomez dated in 2008 (she casually starred in the "Burnin' Up" music video), while Miley and Nick dated a year prior from 2006 to 2007. While Miley seemingly referenced Selena in "7 Things" ("You love me, you like her"), Sel told W magazine in 2016, "We never feuded. We both liked the same guy when we were 16.…We are now completely settled in our own lives.”

Kylie Jenner and Gigi Hadid

Back in 2011, Cody Simpson was in a brief relationship with Kylie Jenner, and here's what he had to say about their split on Hello Ross: "The whole K-O-D-Y thing didn't work for me." Honestly, rude!

Anyway, Cody then dated Gigi Hadid (a close friend of the Kardashian family) after she starred in one of his music videos. They ended things in 2015, and he was similarly chatty about their split.

Katy Perry and Miranda Kerr

While much of this list has a ~sharing the same ex~ vibe, Katy Perry and Orlando Bloom are very much still together. And despite having a partner in common, Katy and Miranda are super close friends and constantly show up to support each other. We love to see it!

Nina Dobrev and Nikki Reed

Ian Somerhalder's most significant relationships are with two blood-sucking besties. First, he dated Nina Dobrev while they were starring on The Vampire Diaries, and then he got together with Twilight's very own Nikki Reed.

Kendall Jenner and Taylor Swift

In a very well-documented (by Taylor herself, tbh) series of events, Taylor dated Harry Styles, circa 2012/2013. (I'm personally still not over him leaving her on that boat.) Then, starting in 2013—and spanning until 2022!—there were on-again-off-again rumors of Kendall dating Harry.

Josh Hutcherson and Avan Jogia

Zoey and Josh (or as I'll always call him, Peeta) dated back in 2012, and Zoey started dating Avan Jogia after they split (these two were together for a full five years).

Dianna Agron and Emma Roberts

Dianna and Alex dated in 2011 while filming I Am Number Four and had an extremely messy breakup. (She allegedly stayed at a hotel "under an alias" to avoid him.) Emma Roberts, meanwhile, dated Alex a few years prior in 2008, and he straight-up got her name tattooed on his finger. Which is...a lot!

Joe Jonas and Wilmer Valderamma

Nope! Your prayers have not been answered! We're still not done with Joe Jonas!

We already know Joe dated Demi, but Joe also happens to be friends with Demi's most long-term ex, Wilmer Valderrama. Joe and Wilmer were even spotted hanging out in Paris back in 2019 with Sophie Turner.

Zoë Kravitz and Blake Lively

Blake and Zoë have been chilling a ton lately, thanks to both of them being close friends with Taylor Swift, but they also have dating Gossip Girl himself in common! Blake and Penn dated while filming the popular CW show, while he and Zoë dated for two years and split in 2013.

Anne Vyalitsyna and Behati Prinsloo

Model Anne Vyalitsyna broke up with Adam Levine after two years of dating and informed the world before telling him—leaving Adam "blindsided"and "heartbroken." But just two months later, he was spotted kissing Behati Prinsloo—a good friend of Anne's. Per a source, "Behati always had a crush on Adam, and she was a little jealous of Anne." Okay then!

Lori Harvey and Kendall Jenner

Lori and Kendall are best friends who hang constantly—and apparently they have the same excellent taste, because they both dated Michael B Jordan. Or *allegedly* dated, in the case of Kendall, since MBJ remained vague when GQ asked him about their 2015 relationship status. "It's the world we live in. They see white and black. I don't," he said. "Kendall's a friend of mine, you know. I don't know her, like, that well, but I know her enough."

Drew Barrymore and Kristen Wiig

Drew and Fabrizio met and started dating in 2002, and stayed together for five full years (pretty much a lifetime in Hollywood). Fabrizio went on to date Drew's friend, Kristen Wiig, a few years later, which Drew had zero problem with it. "It all seems so wacky and incestuous, but that's kind of how life works," she said. "It seems fitting that they would find each other. I was like, 'Right, of course, that makes perfect sense.'"

Selena Gomez and Nicola Peltz

Selena Gomez and Nicola Peltz are best friends—to the point where they joke about being in a throuple with Brooklyn Beckham. But they actually have none other than Justin Bieber in common. The ins and outs of Jelena can be found over here, but if Nicola's name being brought up comes as a surprise, that's because her relationship with Justin was purely speculative and never confirmed. That said, Us Weekly *did* report back in 2016 that they'd been having "sleepovers" at his house.

Ellie Goulding and Taylor Swift

Ellie is actually the one who set Taylor up with Calvin (who she herself was rumored to have dated in 2013). "Calvin is a really great mate, and he's so fantastic, and Taylor is such a cool person who I love," she told The Sun."I thought, 'They're both really awesome and both really tall, they'll be brilliant together."

Jamie Foxx and Tom Cruise

Tom Cruise and Jamie Foxx costarred in Collateral and actually hung out while Katie and Tom were still together. But, uh, apparently they didn't stay close, because Jamie ended up dating Katie after her split from Tom in 2012. Katie and Jamie broke up after five years together in May 2019 and I'm still not over it. (They were cute!)

Rachel Leviss and Ariana Madix

Think we can all agree that Scandoval is the messiest example of two celebs—and, er, former friends—who...dated?...the same person (Tom Sandoval, obviously).

Tony Romo and Chace Crawford

Carrie Fisher dated Dallas Cowboys quarterback Tony Romo in 2007, who is now the brother-in-law of Gossip Girl's very own Chace Crawford, who ALSO dated Carrie. It's a small world, after all.

Elizabeth Taylor and Debbie Reynolds

Ending this list with some Old Hollywood drama! Elizabeth and Debbie were close friends—but after Elizabeth's husband, Mike Todd, passed away, she and Eddie Fisher started having an affair. Debbie and Eddie split, he went on to marry Elizabeth, they split, and Debbie and Elizabeth had a happily ever after when they reunited and starred in These Old Broads (during which they roasted Eddie). The! End!

You Might Also Like

• Here’s What NOT to Wear to a Wedding

• Meet the Laziest, Easiest Acne Routine You’ll Ever Try