Celebrities Who Dated the Same Person and How Everyone, Uhm, Handled It

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.

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.

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.)

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

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.

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…

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.

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.

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)_/¯

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.

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.”

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.

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.

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!)

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!

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 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…