17 Celebrity Best Friends Who Both Dated The Same Person

Hollywood seems to be a pretty big place given the number of actors, musicians, models and performers that can fill up an auditorium for an awards show. But, it’s actually a pretty small place. If you’re a celebrity who only dates celebrities, you might find that the pool of the number of eligible suitors to be surprisingly small. That might be why some celebrity best friends end up dating the same person.

For us non-famous folk, the thought of dating a best friend’s ex is an absolute no. It’s grounds to kill a friendship. In Hollywood, that isn’t always the case. Sometimes, celebrities acknowledge the small dating pool and know that their friendships are stronger than exes and new relationships. Of course, there are times when there’s bad blood and people go from friends to frenemies. Here are 17 celebrity BFFs who dated the same person.

17. Taylor Swift, Gigi Hadid And Joe Jonas

Everyone will remember that Taylor Swift and Joe Jonas dated way back in 2008. He was the boy who reportedly dumped her over a 27-second phone call and inspired “Forever & Always.” Fast forward to 2014 when Gigi Hadid is walking runways, appearing on magazine covers and part of Taylor’s iconic squad. Gigi ends up dating Taylor’s ex, Joe, just before she hooked up with Zayn. But, it didn’t ruin the friendship between the two gals. Taylor even hung out with Joe and Gigi together. Remember that boat ride in London?

16. Katy Perry, Taylor Swift And John Mayer

Yes, it’s Taylor Swift again. Before the alleged backup dancer switch, she and Katy Perry were friends and would hang out and go out to dinner. The dancers obviously caused a rift and it’s likely that so did the fact that they both dated John Mayer. Taylor and John’s relationship was kept under wraps but it reportedly took place around 2009 and ended poorly – if the songs “Dear John” by Tay and “Paper Doll” by John are any indication. Then Katy and John dated on and off from 2012 to 2014.

15. Nina Dobrev, Nikki Reed And Ian Somerhalder

There was so much potential for awkwardness here. Nina DobrevNikki Reed and Ian Somerhalder were all mutual friends. Ian and Nina starred on The Vampire Diaries together and dated on and off for a couple of years before calling it quits for good in 2013. Then Nikki and Ian got together. The two are now married and have a child together. Turns out, there are no hard feelings with any parties. Nikki even posted an Instagram about the bond the three have.

14. Miley Cyrus, Selena Gomez And Nick Jonas

There always seems to be some drama brewing in the world of Young Hollywood whether it’s real or exaggerated. What is true is that Disney stars Miley Cyrus and Selena Gomez were involved in a love triangle of sorts with Nick Jonas. SelGo and MiCy were good friends – riding the Disney Channel wave during the height of Hannah Montana and Wizards of Waverly Place. Nick and Miley reportedly dated from 2006 before breaking up. Then Selena and Nick got together. Way back in 2008, the “Bad Liar” songstress told Twist magazine, “My favorite song that I’ve written is called ‘I’m Sorry.’ It’s about a boy I kind of fell for, but he couldn’t let his ex-girlfriend go, and it was really difficult.” Miley apparently wrote “7 Things” about the JoBro, too. Years later, Miley Cyrus infamously sung a song called “F U” to a cardboard cut-out of Selena Gomez, leading to rumors that she still wasn’t over her former friend “stealing” Nick from her.

13. Jennifer Aniston, Courteney Cox And Adam Duritz

We couldn’t imagine anything coming between Jennifer Aniston and Courteney Cox. They seem to be as inseparable in real life as they were as Monica Geller and Rachel Green on Friends. So, you might be surprised to hear that they dated the same person, Counting Crows front man Adam Duritz. Oh, and this was around the same time as Friends was airing. Adam revealed he briefly dated Jen around 1995 and dated Courteney a few years later after she starred in his “A Long December” video.

12. Taylor Swift, Selena Gomez And Taylor Lautner

Are you keeping track of the number of times that Taylor Swift is on the list? This time it involves her and Selena Gomez. Taylor Swift and Taylor Lautner had a high profile relationship when they dated for a few months in 2009. That fizzled out and soon Twihards were going crazy when Selena and Taylor Lautner were spotted together in Vancouver. Their apparent relationship was brief, too. This seems to be another example where the friendship survived the relationship because Selena and Taylor still seem to be BFFs.

11. Nikki Reed, Ashley Greene And Ryan Phillippe

Nikki Reed and Ashley Greene were both costars in the Twilight franchise and were frequently photographed arm-in-arm on the red carpet. It seems that there wasn’t any animosity between them for dating the same person. There were rumors that Ryan dated Nikki, his Lords of Dogtown costar, after splitting from then-wife Reese Witherspoon around 2007. In 2013, he got together with Ashley. Hollywood’s one small town!

10. Lance Armstrong, Owen Wilson And Sheryl Crow

Think back to the 1990s, and you might recall that Owen Wilson dated Sheryl Crow around the time the two starred in 1999’s The Minus Man. In 2003, Owen’s friend Lance Armstrong started dating the country singer. The two ended up dating for three years, got engaged, but split in 2006. There were rumors that Owen was “pretty upset” about the betrayal, and then it was said that Lance did it again! This time, in 2008, he dated Owen’s even more recent ex! Stay tuned to find out who…

9. Cameron Diaz, Kate Hudson And Alex Rodriguez

As of 2018, Alex Rodriguez appears to be pretty smitten with Jennifer Lopez. Back in the late 2000s, he was going out with Cameron Diaz and Kate Hudson. The situation might have been a bit tense considering the two ladies were friends. A-Rod dated Kate for a few months in 2008 when she was pictured at numerous baseball games. Shortly after, Alex got together with Cameron. It’s reported the relationship lasted a year. At least we still have that infamous popcorn-feeding photo to remember their relationship by…

8. Lance Armstrong, Owen Wilson And Kate Hudson

Yes, it’s Owen Wilson and Lace Armstrong again. This time, the girl in the middle is Kate Hudson. After working together on You, Me and Dupree in 2006, Kate and Owen dated for a while then they were on and off. Around 2008, Kate started dating Lance. They dated for a few months and it’s up for debate whether Owen and Lance’s friendship survived.

7. Taylor Swift, Ellie Goulding And Calvin Harris

Rumors swirled that Ellie Goulding and Calvin Harris were a couple after collaborating on “Outside” and “I Need Your Love.” They reportedly dated in 2013 before calling it quits. So, some might be surprised to hear that it was Ellie who actually introduced friend Taylor Swift to Calvin. It all happened at the 2015 Brit Awards. Taylor and Calvin dated for a year before splitting up in 2016 and Taylor moved on to Tom Hiddleston.

6. Gwyneth Paltrow, Jennifer Aniston And Brad Pitt

Gwyneth Paltrow and Jennifer Aniston are A-list celebrities, but we don’t see or hear much about their friendship compared to some squads. Turns out they have a friendship, having attended different parties and made positive comments about each other in the media. And the friendship goes above them both dating Brad Pitt. Gwyneth dated Brad from 1994 to 1997 and they were even engaged. About a year later, Jen and Brad got together, eventually marrying in 2000. As we know, they famously split in 2005.

5. Heather Locklear, Denise Richards And Richie Sambora

Listen up because we’ve got marriage and friends involved. Heather Locklear was married to guitarist Richie Sambora from 1994 to 2007. A couple of months after they split, Richie started dating the family’s close friend Denise Richards, who had recently split from Charlie Sheen. Many assumed the romantic relationships killed Denise and Heather’s friendship, but Denise is quoted that that her friendship with Heather was finished before the relationship drama. There’s a story there, we know it!

4. Drew Barrymore, Kristen Wiig And Fabrizio Moretti

Funny girls Drew Barrymore and Kristen Wigg seem to share the same taste in men in addition to having the gift of comedy. For example, Drew dated The Strokes drummer Fabrizio Moretti for five years from 2002 to 2007. In 2012, Kristen got together with Fabrizio. That relationship lasted about a year. What seemed to survive is Drew and Kristen’s friendship. Drew previously spoke out about how it seemed almost fitting Fabrizio and Kristen would find each other.

3. Drake, The Weeknd And Bella Hadid

Around 2011, Canadian performers The Weeknd and Drake were reported to be good friends and collaborators. The two performed together and worked on Drake’s “Take Care” album. The Weeknd went on to date model Bella Hadid for over a year before they split in 2016. Then there were many reports that Drake “broke the bro code” and hooked up with Bella around her birthday and splurged on a special gift for her. Not long after, Drake allegedly ghosted Bella. So, it seems like there are no happy people in the situation.

2. Ashley Greene, Taylor Swift And Joe Jonas

Surprise, surprise Taylor Swift is back on the list. And Ashley Greene makes her second appearance, too. It’s all thanks to Joe Jonas. We’ve discussed how Taylor and Joe dated in the late 2000s. He eventually hooked up with Ashley in 2010 before they split. People could say things came full circle when Joe and Ashley ran into each other at a Taylor Swift concert in 2011.

1. Zayn, Joe Jonas And Gigi Hadid

Speaking of Joe Jonas, he has often been compared to Zayn Malik, so it’s interesting that the two dudes would end up having Gigi Hadid in common. As previously discussed, Joe had a high profile romance with the supermodel. She quickly moved on with Zayn. The two dated for about two years and recently called it quits. After news of Zigi getting together went public in ’15, Joe deleted a photo of himself and Zayn at fashion week together from his social media and unfollowed Gigi. It’s safe to say there was a bit of bad blood.

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