In Hollywood, everyone’s in everyone else’s business. Friends, acquaintances, and gossip spread like wildfire. And dating here is the trickiest and messiest of all! Lots of stars have dated or married the same people, like Angelina Jolie and Jennifer Aniston (both dated Brad Pitt) or Brad Pitt and Justin Theroux (both dated Jennifer Aniston).
In this article, we’ve got the scoop on 40+ celebrities who share the same exes. Keep reading to discover who they are and the drama that comes with sharing an ex!
Justin Bieber and Shawn Mendes
Back in 2018, Hailey Baldwin (now Hailey Bieber) and Shawn Mendes were an item, according to rumors. They even showed up together at the Met Gala! But soon after, Hailey moved on and began dating Justin Bieber. The two got married soon after and are now expecting to welcome their first child together.
Travis Scott And Tyga
Tyga and Travis Scott both had relationships with Kylie Jenner. Tyga met Kylie for the first time when she was 14 back in 2011 and even threw her 17th birthday party. However, they didn’t officially start dating until she was 18, but they broke up in 2017.
Kylie then started dating Travis Scott in 2017. Their relationship had an on-again, off-again dynamic until late 2022, and they now have two children together.
Courteney Cox and Jennifer Aniston
Jennifer Aniston and Courteney Cox from Friends have dated Adam Duritz, the singer from Counting Crows. Aniston and Duritz had a fling after they met each other at The Viper Room in 1995.
During a VICE TV docuseries, Duritz spoke highly of Aniston and complimented her.
Entertainment Tonight also shared a clip of Duritz talking about Anniston.
“She was really nice, really funny, really pretty, those were pretty good requirements for me and also she liked me. It didn’t last very long, but she’s a nice girl,” he said.
After Aniston, Duritz had a brief relationship with Cox. She even appeared in the music video for the Counting Crows’ song “A Long December” in 1997.
Grimes & Vittoria Ceretti
Grimes revealed her new relationship with DJ Anyma through a series of Instagram photos on March 22.
Before this, DJ Anyma was married to Vittoria Ceretti.
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Demi Lovato and Taylor Swift
Get ready for some serious spice because we’re now getting into the Jonas Brothers drama!
In 2018, Taylor Swift was with Joe Jonas until their famous 27-second breakup call. After this, Joe dated Demi Lovato, his co-star from Camp Rock, around 2010.
Taylor Swift and Sophie Turner
Joe Jonas got married to Sophie Turner, the Game of Thrones star, in 2019, and the adorable couple had two babies together. However, they split publicly in September 2023.
Surprisingly, Taylor and Sophie started hanging out a lot after the breakup and Taylor even loaned Sophie one of her apartments to stay in.
Jason Patric and Kieffer Sutherland
Back in 1991, Kiefer Sutherland got engaged to Julia Roberts, but she called it off three days prior to their wedding. She then went off to a different country, Ireland, with The Lost Boys co-star (one of Kiefer’s close friends too), Jason Patric. It’s like a movie plot, right?
But Kiefer holds no grudges. In a 2006 interview with Rolling Stone, he praised Julia for recognizing how young and silly they were, even at the last minute. He said,
“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. Thank God she saw it.”
Bella Hadid and Simi Haze
In 2022, The Weeknd shocked everyone when he was seen with Simi Haze, his ex Bella Hadid’s best friend. Bella seemed just as shocked and quickly unfollowed Simi’s Instagram account. As for The Weeknd and Simi, they appear to be a strong couple till now!
Taylor Lautner and Jamie Campbell Bower
Taylor Lautner and Jamie Campbell Bower have got a couple of things in common. They’ve both been with Lily Collins, and they’ve starred in the spectacular Twilight SAGA.
Selena Gomez and Taylor Swift
Taylor Lautner and Selena Gomez were reported to have dated briefly after they met each other in 2009 on the set of Ramona and Beezus.
Additionally, Taylor Swift and Taylor Lautner also dated that same year, and her song “Back to December” is about him.
Lance Armstrong and Owen Wilson
Let’s rewind to the early 2000s, a time when celebrity relationships were often a bit too chaotic. Owen Wilson and Sheryl Crow got together in 1999, but unfortunately, their romance didn’t last. Sheryl soon moved on to Lance Armstrong, Owen’s close friend, and even got engaged to him. But Owen seemed to handle the news of their relationship well, as he and Lance stayed friends.
After his breakup with Sheryl, Lance Armstrong dated another ex of his friend’s—Kate Hudson. They got together soon after Kate split with Owen in 2008. Talk about a complicated love triangle!
Nick Cannon and Nick Lachey
Nick Cannon and Nick Lachey share more than just a common first name. They both dated Kim Kardashian before Lachey, the Love Is Blind co host, made an appearance on Cannon’s show, The Masked Singer, in 2021.
However, Cannon’s brief relationship with Kim was more involved than Lachey’s.
Lachey revealed during an appearance on Watch What Happens Live with Andy Cohen in 2019 that he only went on one date with Kim. He even joked that calling her his “ex” was a bit of a stretch, saying, “I think we went on one date together.”
Gwyneth Paltrow and Drew Barrymore
Drew Barrymore and Luke Wilson were a couple in the mid-90s for three years and stayed friends after their breakup.
Later, Gwyneth Paltrow and him sparked a romance after working together on the 2001 movie The Royal Tenenbaums.
Chris Pine and Channing Tatum
Channing Tatum is engaged to Zoë Kravitz and the couple is looking extremely cute together. But before Channing came into the picture, Zoë was with Chris Pine around 2010.
Chris and Channing are good friends, and they were even seen biking around D.C. together in 2018.
Ben Affleck and Bradley Cooper
Between Bennifer’s 2004 split and their reunion and marriage in 2022, there were rumors that Bradley Cooper and Jennifer Lopez were together in 2011.
One source revealed to People that “She does like his attention, and it makes her feel good that he seems so into her.”
Zoe Saldaña and J.Lo
Moving on to Zoe Saldaña, she and Bradley were in a more serious relationship. They dated in 2012 for four months before Bradley reportedly ended things. However, they were together again for a while, but broke up again in January 2013.
Zoe Saldaña and Renée Zellweger
Before Zoe, Bradley was with Renée Zellweger. They dated for approximately two years and then she ended the relationship in 2011. According to Us Weekly, Bradley’s intense focus on his career was a factor in their split.
Gigi Hadid and Taylor Swift
Taylor Swift and Gigi Hadid have a bit of crossover in their dating lives. Taylor and Joe Jonas were together in 2008, and seven years later, Gigi, Taylor’s model BFF, was also linked to him.
Taylor and Joe’s breakup was pretty dramatic. Taylor even called him out on The Ellen DeGeneres Show for ending their relationship over a brief phone call. Over the years, though, they repaired their friendship, especially when Joe and Gigi started seeing each other. They were even spotted together at Taylor’s Fourth of July party in 2015, hanging out with other celebs.
Gigi and Joe’s relationship, however, didn’t last long. They broke up after just five months that fall. At the time, a source revealed to People that “it wasn’t a dramatic breakup. It was just hard to make it work with their schedules. They will definitely remain friends.”
Joe Jonas and Zayn Malik
After Gigi Hadid and Joe split, Gigi quickly got with Zayn Malik. Even Joe acknowledged how quickly Gigi moved on, saying, “I think it’s interesting that she moved on so quickly. I mean it was definitely very quick.” Moreover, he even removed a photo of him with Zayn and Kanye West that he had captioned “Squad.” Awkward!
George Harrison and Eric Clapton
Switching gears to the music world, Pattie Boyd was married to George Harrison back in the 1960s. Things got a bit messy when she grew closer to Eric Clapton, one of Harrison’s good friends, who also fell in love with her. Pattie eventually went on to leave George and she married Eric, but they all managed to stay friends.
Cameron Diaz and Kate Hudson
Now, it’s time to move on to the rumored drama between Cameron Diaz and Kate Hudson. During the mid-2000s, Kate got together with Justin Timberlake soon after his split from Cameron. This rumor sparked a lot of gossip, but it’s just the tip of the iceberg as their drama gets even more juicier!
Things between them got heated up again when Cameron started dating Alex Rodriguez after his split with Kate. In 2010, Us Weekly reported that Kate saw this as payback. On the other hand, a friend of Cameron’s claimed that Cameron thought Kate’s anger was a joke, explaining that Cameron had been in a serious relationship with Justin and suggesting that Kate was upset just because she didn’t like being single. Yikes!
Katy Perry and Taylor Swift
In the world of pop, John Mayer and Taylor Swift had a brief relationship around 2009/2010, which inspired Taylor’s song “Dear John.” Not long after, John began dating Katy Perry. Despite the timing, it doesn’t seem like this is what sparked any “bad blood” between Katy and Taylor.
Selena Gomez and Miley Cyrus
Selena Gomez and Miley Cyrus shared a history with Nick Jonas from their Disney Channel days. Miley started dating Nick when they were both just 13 in 2006. She later told Seventeen Magazine that their relationship was genuine love, though they stayed friends after breaking up.
Selena began dating Nick in 2008, and she even met her future best friend, Taylor Swift, on a double date with Nick’s older brother, Joe. Selena and Nick had an on-and-off relationship until 2010. Selena later described their romance as “puppy love” and confirmed they stayed friendly.
Miley seemed to mention Selena in her song “7 Things” with the line, “You love me, you like her.” But in a 2016 interview with W Magazine, Selena clarified, “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, Kylie Jenner briefly dated Cody Simpson. When they split, Cody shared his thoughts on Hello Ross, saying, “The whole K-O-D-Y thing didn’t work for me.” Ouch!
Cody then dated Gigi Hadid, who is a close friend of the Kardashians, after she appeared in one of his music videos. Their relationship ended in 2015, and Cody didn’t hold back his feelings about that split either.
Katy Perry and Miranda Kerr
Even though Katy and Miranda share a partner in common—Orlando Bloom—they’re actually great friends. They often show up to support each other, which is lovely to see!
Plus, Katy and Orlando seem to be going pretty strong till now!.
Elizabeth Taylor and Debbie Reynolds
Elizabeth Taylor and Debbie Reynolds were close friends until Elizabeth’s husband, Mike Todd’s, demise. This led Elizabeth to have an affair with Eddie Fisher. After Debbie and Eddie split, he married Elizabeth. They also eventually split, but Debbie and Elizabeth reunited and even starred in These Old Broads, where they had a bit of fun roasting Eddie.
Tony Romo and Chace Crawford
In a quirky twist, Carrie Fisher dated Tony Romo, the Dallas Cowboys quarterback, in 2007. Tony is now the brother-in-law of Chace Crawford, who also dated Carrie.
Rachel Leviss and Ariana Madix
Rachel Leviss and Ariana Madix had their own drama with Scandoval, which is a prime example of how messy things get with two former friends sharing the same person—Tom Sandoval, of course.
Jamie Foxx and Tom Cruise
Jamie Foxx and Tom Cruise worked together in Collateral and hung out while Tom was with Katie Holmes. Later, Jamie ended up dating Katie after her split from Tom in 2012. Their relationship lasted five years before they broke up in May 2019.
Ellie Goulding and Taylor Swift
Ellie Goulding played matchmaker for Taylor Swift and Calvin Harris. Ellie had once been rumored to have dated Calvin in 2013. She shared with The Sun, “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.’”
Selena Gomez and Nicola Peltz
Selena Gomez and Nicola Peltz are the bestest of friends and even joke about being in a throuple with Brooklyn Beckham. However, they only share one connection through Justin Bieber.
While Selena’s relationship with Justin was very public, Nicola’s rumored involvement with him was never officially confirmed. However, Us Weekly did report in 2016 that Nicola and Justin had been having “sleepovers” at his house.
Drew Barrymore and Kristen Wiig
Drew Barrymore and Fabrizio Moretti were together for five years starting in 2002, which is quite a long time in Hollywood. After their split, Fabrizio dated Drew’s friend, Kristen Wiig. Drew didn’t mind at all and even found it fitting. She said, “It all seems so wacky and incestuous, but that’s kind of how life works. It seems fitting that they would find each other. I was like, ‘Right, of course, that makes perfect sense.'”
Lori Harvey and Kendall Jenner
Lori Harvey and Kendall Jenner are close friends and seem to have similar tastes in men. Both have been linked to Michael B. Jordan. Kendall’s connection to MBJ is less clear, as he was vague about their rumored 2015 relationship when asked by GQ. He said, “It’s the world we live in. They see white and black. I don’t. Kendall’s a friend of mine, you know. I don’t know her, like, that well, but I know her enough.”
Anne Vyalitsyna and Behati Prinsloo
The famous model Anne Vyalitsyna ended her two-year relationship with Adam Levine and announced it publicly before telling him, leaving him “heartbroken” and “blindsided.”
Just two months later, Adam was seen kissing Behati Prinsloo, who was a friend of Anne’s. A source revealed that Behati had always had a crush on Adam and felt a bit “jealous of Anne”.
Zoë Kravitz and Blake Lively
Blake Lively and Zoë Kravitz have been spending a lot of time together recently, thanks to their mutual friendship with Taylor Swift. They also share a connection through their past relationships with Penn Badgley. Blake and Penn got together while working on Gossip Girl, and Zoë and Penn were together for two years before breaking up in 2013.
Joe Jonas and Wilmer Valderamma
We’re still not done talking about Joe Jonas and his relationships yet!
Aside from his well-known romance with Demi Lovato, Joe is also friends with Wilmer Valderrama, Demi’s long-term ex. In 2019, Joe and Wilmer were seen hanging out in Paris along with Sophie Turner.
Dianna Agron and Emma Roberts
Dianna Agron and Alex Pettyfer had a dramatic breakup after dating while filming I Am Number Four in 2011. Dianna even reportedly moved into a hotel under an alias in order avoid him.
Meanwhile, Emma Roberts, who dated Alex a few years earlier in 2008, had her name tattooed on his finger, which is definitely a bold move!
Josh Hutcherson and Avan Jogia
Josh Hutcherson (Peeta for many of us) dated Zoey Deutch in 2012. After their split, Zoey began a five-year relationship with Avan Jogia.
Kendall Jenner and Taylor Swift
Kendall Jenner and Taylor Swift have both been with Harry Styles. Taylor dated him around 2012/2013, and there were on-again-off-again rumors about Kendall and Harry from 2013 until 2022.
Nina Dobrev and Nikki Reed
Nina Dobrev and Nikki Reed might seem like they’d have drama given their connections to the same ex, but they’ve actually managed to stay friends. Nina dated her Vampire Diaries co-star Ian Somerhalder from 2010 to 2013, mirroring their on-screen romance. In 2015, Ian married Twilight star Nikki Reed in Malibu after dating for about a year. The couple has two kids: a daughter, Bodhi, born in 2017, and a son, born in 2023.
Bethenny Frankel And Aurora Culpo
Bethenny Frankel and Paul Bernon were together from 2018 until May 2024, when they ended their engagement. Shortly after their split, Paul was seen with Aurora Culpo, but they might have parted ways as well, according to Page Six.
Bethenny shared on her podcast that learning about her ex-fiancé moving on with another woman so quickly was very painful. “Hearing about your ex-fiancé committing to another woman shortly thereafter on their first date, and then being inside their relationship hearing about their sex and their gifts and meeting each other’s kids and the level of commitment… It was gutting. It was brutal,” she said.
Bridget Moynahan And Gisele Bundchen
Bridget Moynahan and Gisele Bündchen both have children with Tom Brady. Bridget dated Tom from 2004 to 2006, and Gisele was married to him until 2022.
Demi Moore And January Jones
Demi Moore and January Jones both dated Ashton Kutcher. January and Ashton were together for about three years, from 1998-2001. On the other hand, Demi and Ashton’s relationship lasted from 2003 to 2013. They got married in 2005 but split in 2011, finalizing their divorce in 2013.
Gigi Hadid And Perrie Edwards
Gigi Hadid and Perrie Edwards share more than just their beauty—they both dated Zayn Malik. Perrie and Zayn were together since 2011, got engaged in August 2013, but ended their relationship in 2015 after Zayn reportedly broke up with her via text, according to Cosmo. That same year, Zayn started dating Gigi.
Gigi and Zayn had an on-again, off-again relationship starting in November 2015. They welcomed their daughter, Khai, in September 2020. However, they officially broke up in 2021 following an incident involving Gigi’s mother, Yolanda, but they continue to co-parent.
Angelina Jolie And Madonna
Angelina Jolie and Madonna both dated Jenny Shimizu, a model, in the 1990s. Madonna and Jenny were together from 1993 to 1994, but their relationship wasn’t widely known until Jenny spoke about it in 2007.
Meanwhile, Angelina and Jenny were involved from 1994 to 2000. In a 1997 interview with Girlfriends, Angelina revealed, “I probably would have married Jenny Shimizu if I hadn’t married my husband. I fell in love with her the first second I saw her.”
Pete Davidson And Eric Andre
It might surprise some, but both comedians Pete Davidson and Eric Andre have been romantically involved with supermodel Emily Ratajkowski. Following her split from Sebastian Bear-McClard, Ratajkowski was seen with a few high-profile men, including Davidson and Andre, toward the end of 2022 and into early 2023.
Jenny Slate And Minka Kelly
Jenny Slate and Minka Kelly both share an ex who is a Marvel star—Chris Evans.
Kelly and Evans had a rocky relationship, dating on and off from 2007 (according to rumors), with a public romance from 2012 to 2013, and hanging out again two years later, in 2015.
Slate, on the other hand, dated Evans for about a year in 2016 and then their romance got rekindled from 2017 to 2018.
Lindsay Lohan And Sara Paxton
Lindsay Lohan and Sara Paxton both had serious relationships with Nico Tortorella, known for his role on Younger.
From 2009 to 2012, Paxton and Tortorella were together. A year later, Tortorella started seeing Lohan. Their romance was quite intense, and they were even engaged from 2013 to 2015!
Vanessa Hudgens And Lily-Rose Depp
You might remember Vanessa Hudgens and Austin Butler as a couple, but did you know Austin also dated Lily-Rose Depp between Vanessa and Kaia Gerber? The two were spotted sharing some serious PDA in 2021, according to Page Six.
Joey King And Kaia Gerber
Even Euphoria stars have their share of dating drama! Both Joey King and Kaia Gerber were romantically involved with the same Euphoria star, Jacob Elordi.
Joey and Jacob first crossed paths while filming The Kissing Booth. They began dating in 2017 and stayed together until 2018. Fast forward to 2021, and Jacob was linked to Kaia Gerber, with their relationship lasting about a year.
Ariana Grande, Kim Kardashian, and Kate Beckinsale
At one point, Ariana Grande, Kim Kardashian, and Kate Beckinsale all dated Pete Davidson.
In May 2018, Pete made headlines for his relationship with Ariana Grande. The couple was very public about their romance, even getting engaged after less than a year together, but split up in October 2018.
Shortly after, in January 2019, Pete was seen with Kate Beckinsale. Despite their 20-year age gap, their relationship seemed strong until they ended things in April 2019.
Pete then began dating Kim Kardashian in October 2021. Their connection sparked after an on-screen kiss on SNL, and it was Kim’s first relationship since her split from Kanye West. Despite their nine-month romance and several tattoos, they announced their breakup in August 2022.
