15 Celebs Who Had the Same Ex

Hollywood can feel like a close-knit community, and that often extends to who celebrities date. It’s surprisingly common for stars to date the same people, whether it’s fellow actors or other industry insiders. Sometimes this leads to drama and public disagreements, but other times, everyone handles it respectfully. Looking at these shared romantic histories gives us a peek into how connected the world of celebrity relationships really is. Here’s a look at fifteen famous pairs who have all dated the same person.

Selena Gomez & Miley Cyrus

Miley Cyrus and Selena Gomez both dated Nick Jonas, the youngest of the Jonas Brothers. He first dated Cyrus while she was starring in ‘Hannah Montana,’ and then began a relationship with Gomez soon after. This quick succession of relationships reportedly caused some tension between the two actresses when they were teenagers in the late 2000s. However, both Cyrus and Gomez have since confirmed they’ve resolved any past issues and are on good terms. They’ve each gone on to achieve significant success in their own music and acting careers, putting their shared history behind them.

Jennifer Aniston & Angelina Jolie

The relationship between Brad Pitt and actresses Jennifer Aniston and Angelina Jolie was a major tabloid obsession in the early 2000s. Aniston and Pitt were married for five years before publicly separating in 2005. Shortly after, Pitt began a relationship with Jolie, eventually marrying her after they met while filming ‘Mr. & Mrs. Smith’. For over ten years, the media fueled a story of competition between the two actresses, even though neither publicly addressed it. Both women have continued to thrive in their careers and have become more private about their personal lives in recent years.

Taylor Swift & Katy Perry

Both Taylor Swift and Katy Perry famously dated singer John Mayer. Swift had a short relationship with him in 2009 and is believed to have written the song ‘Dear John’ about it. Perry then dated Mayer on and off for several years, until 2014. Though the two singers had a public falling out professionally, they’ve since made up and moved past their disagreements. Their history with John Mayer remains a memorable part of both of their dating lives.

Cameron Diaz & Kate Hudson

Both Cameron Diaz and Kate Hudson dated baseball player Alex Rodriguez. Kate Hudson was often spotted at his New York Yankees games while they were together in 2009. Shortly after their split, Diaz began dating Rodriguez. Despite both having a relationship with the same famous athlete, the two actresses remained friends. Rodriguez later went on to date other celebrities, including a lengthy engagement with Jennifer Lopez.

Hilary Duff & Lindsay Lohan

In the early 2000s, Hilary Duff and Lindsay Lohan were publicly caught in a rivalry over singer Aaron Carter. Carter briefly dated Duff, then Lohan, and then returned to Duff, which caused a lot of tension between the actresses, often reported in teen magazines. Carter later acknowledged he was responsible for the conflict. Eventually, both Duff and Lohan moved past the drama as they grew older.

Leonardo DiCaprio & Tom Brady

Okay, so as a movie and sports fan, this is a story I always find interesting. Leonardo DiCaprio and Tom Brady both dated Gisele Bündchen – talk about a power couple! Leo and Gisele were the it couple in the early 2000s, seriously everywhere you looked. They were together for five years, but it didn’t last. Then Gisele met Tom, and they ended up getting married and having two kids. She’s mentioned that her time with Leo helped her grow as a person, which is cool. And honestly, both guys are still crushing it in their careers – Leo with the films and Tom, well, he’s a football legend!

Nikki Reed & Nina Dobrev

Nina Dobrev and Nikki Reed are connected through their relationship with actor Ian Somerhalder. Dobrev and Somerhalder dated for several years while working together on ‘The Vampire Diaries.’ Reed later began a relationship with Somerhalder, and they eventually married and had children. Despite speculation about tension between them, the three have been seen together looking friendly, and have worked to disprove rumors of any bad blood, supporting each other and their families.

Courteney Cox & Jennifer Aniston

Courteney Cox and Jennifer Aniston have remained close friends even though they both dated the same man, Adam Duritz, the lead singer of Counting Crows. Aniston had a short relationship with Duritz in the mid-1990s, followed by a longer relationship between him and Cox, which included Cox appearing in Counting Crows’ music video for ‘A Long December.’ Despite these overlapping relationships, the two actresses stayed best friends and are still very close today. Duritz himself has often spoken positively about his time with both of them.

Heidi Klum & Mel B

Okay, so this is a bit of a wild Hollywood story! Eddie Murphy has dated both Heidi Klum and Mel B, and it gets complicated. Mel B and Eddie had a daughter, Angel, back in 2006. Then, after things ended with Mel B, Eddie briefly dated Heidi Klum. There was even some drama with figuring out who Angel’s father was, which was tough. But you know what’s really interesting? Both Heidi and Mel ended up working together as judges on ‘America’s Got Talent’ and seemed to get along great, which is cool to see after everything!

Matt Damon & Johnny Depp

In the 1990s, Winona Ryder had relationships with both Matt Damon and Johnny Depp. Depp and Ryder were a highly publicized couple and were briefly engaged. Damon later dated Ryder, and they were seen together publicly a few times before ending their relationship. Both actors have since married and started families. Ryder remains a significant romantic connection for both men, especially during their early careers.

Taylor Swift & Selena Gomez

Taylor Swift and Taylor Lautner had a short romance in 2009 after working together on the movie ‘Valentine’s Day’. Before dating Swift, Lautner was actually linked to her friend, Selena Gomez. They were seen together in Vancouver while each worked on separate films. Despite the complicated connections, the three have remained amicable. Swift is rumored to have written the song ‘Back to December’ as an apology to Lautner after their split.

Justin Timberlake & Colin Farrell

Britney Spears famously dated both Justin Timberlake and Colin Farrell. Her relationship with Timberlake defined celebrity couples in the late 90s, but ended unexpectedly in 2002. Shortly after, she was seen with Farrell, who downplayed their connection as just casual fun. During both relationships, Spears faced intense media attention regarding her love life. Both Timberlake and Farrell have later discussed the difficulties of being in a public relationship.

Ben Affleck & Marc Anthony

Jennifer Lopez has had important relationships with both Ben Affleck and Marc Anthony. She and Ben Affleck were engaged in the early 2000s, broke up, and then surprisingly got married twenty years later. Lopez was married to Marc Anthony for ten years, and they have twins together, Max and Emme. Despite their history, the two men are said to have a respectful relationship, prioritizing their children and the blended family. Lopez views both relationships as key parts of her life journey.

Kristen Wiig & Drew Barrymore

Kristen Wiig and Drew Barrymore both had relationships with Fabrizio Moretti, the drummer for The Strokes. Drew Barrymore dated him for five years in the mid-2000s, and Kristen Wiig began dating him a few years later, with their relationship lasting about a year and a half. Barrymore has said that while the situation of dating the same person seemed strange, it actually felt right. Despite this, the two actresses have stayed close and continue to support each other.

Kanye West & Nick Cannon

Kim Kardashian has had relationships with both Nick Cannon and Kanye West. She briefly dated Nick Cannon in 2006, before her reality show made her famous. Kanye West and Kim Kardashian were friends for many years before becoming a couple and eventually marrying. They had four children together, but later divorced. Nick Cannon has often spoken fondly of his past relationship with Kim and her family.

Please share your thoughts on which celebrity pair surprised you the most in the comments.

2025-11-27 17:46