12 Celebs Who Dated Their Friends' Exes

Breaking up can be an incredibly awkward process. It’s even more painful and weird when you and your ex have lots of mutual friends. Social situations can get really uncomfortable, and your friends feel as though they have to “pick a side.”

Then there are the times when one of your friends actually does pick a side—the side of your ex. As in, your friend starts dating your ex. In some social circles, this is OK, if both people in the previous relationship truly have no more romantic feelings for one another. Dating a friend’s ex may also be acceptable if the previous relationship didn’t last very long or wasn’t “serious.” However, there are some people who believe that a friend’s ex is off limits, regardless of the circumstances of the breakup. That’s probably a pretty safe rule, because dating a friend’s ex could make things even more awkward at the next social gathering. Not to mention, this could break up friendships.

Apparently, there are some people in Hollywood who didn’t quite get the memo about not dating their friends’ exes. It’s pretty clear that on some issues, Hollywood plays by a different set of rules. Here are 12 celebrities who have dated their friends’ exes.


12 Ashley Greene

Actresses Nikki Reed and Ashley Greene both starred in the Twilight movies together. They also have something else in common—handsome actor Ryan Phillippe. Apparently Phillippe has been making his rounds in the love department after his divorce from Reese Witherspoon (the former couple also have two children together), and has a thing for actresses. Ryan and Nikki were seen at Winston’s in Hollywood, and drove off together in his car. Years later, Phillippe was seen with Ashley Greene, leaving Vignette Lounge with her. They were both trying to hide their faces from the camera. Maybe they were tired of having their pictures taken. Or maybe Greene knew she’d broken the “girl code” by dating Phillippe and didn’t want Reed to find out.

11 Kristen Wiig

Drew Barrymore and Fabrizio Moretti were a couple years ago, but Barrymore ended the relationship in 2007. Five years later, actress and comedienne Kristen Wiig, started dating Moretti. In true Drew Barrymore fashion, she commented on Wiig and Moretti’s relationship in a positive way in 2013. Barrymore stated that “it all seems so wacky and incestuous, but that’s kind of how life works.” While we can’t agree that any part of life should be incestuous, we get the sentiment and it’s clear that there are no hard feelings of Barrymore’s part. Wiig also stated that she’s never been happier and was very lucky to have Moretti when the two started their relationship.

10 Niall Horan

Justin Bieber and One Direction’s Niall Horan apparently had a bit of a “bromance” in 2012. Justin Tweeted to Niall, “what’s up bro,” to which Horan replied “around for a while, getting album 2 ready!” This may have indicated that the two wanted to work together at some point, or that they were genuine friends and just checking up on each other. Then Selena Gomez (also known as Justin Bieber’s first love), was out and about in Hollywood with Horan. Many people think this was an attempt to get Bieber’s attention and make him jealous, while others think Gomez just wanted to have a good time. Either way, it’s highly likely that she could have chosen someone else to be seen with in public with.

9 Selena Gomez


Not only has Selena Gomez dated a friend of Justin Bieber’s, she’s also had a friend date one of her exes. Even in Hollywood, what goes around comes around. Nick Jonas, whose single “Jealous” has been doing quite well, could have been writing the song for a number of reasons. The girl he wrote the song about is now his ex (she’s also featured in the video), but the song could also be about the fact that his ex, Miley Cyrus, started dating Patrick Schwarzenegger. Cyrus and Gomez were friends at one point, but allegedly, things went downhill in the friendship when Gomez started dating Jonas. Selena even wrote a song called “I’m Sorry,” about an ex-boyfriend who didn’t want to let go of the relationship. Could that have possibly been about Nick Jonas?

8 Demi Lovato

Looks like those Jonas brothers just can’t stay out of trouble when it comes to dating popular singers and actresses. Taylor Swift and Joe Jonas had a brief relationship in 2008, and Jonas was the inspiration behind her song “Forever and Always.” The lyrics in the song, which include, “you didn’t mean it, baby. You said forever and always.” Looks like Joe had quite an effect on Taylor. However, Jonas moved on and started dating Demi Lovato in 2010. Lovato stated that “When you go through heartbreaks and things like that, you always have in mind somebody. We were in a relationship and we broke up, and at one point I was really mad at him.” Demi and Joe seem to be on good terms now, and Lovato has also confirmed that she and Taylor Swift are still friends.

7 Cameron Diaz

Apparently, baseball player Alex Rodriguez is pretty appealing, especially to blond actresses. Rodriguez has dated both Kate Hudson and Cameron Diaz, but the details are cloudy when it comes to who dated him first. Hudson and Rodriguez were together for less than a year. Shortly after their breakup, Cameron Diaz was seen leaving Alex’s house with an overnight bag a few months after the Rodriguez/Hudson breakup. Now, everyone involved has moved on. Alex Rodriguez started dating WWE Diva Torrie Wilson, Kate Hudson had a child with Matt Bellamy, and the two got engaged (they have since split up) and Cameron Diaz is married to Benji Madden.

6 Taylor Swift

Taylor Swift and Selena Gomez both had relationships with actor Taylor Lautner. Looks like Swift’s rules about empowering women kind of went out the window when it came to Lautner. Taylor Lautner and Selena Gomez allegedly met when they were staying at the same hotel in Vancouver. Reportedly, they hit it off, but their romance was short-lived, mainly because they were tired of being followed by paparazzi. Swift and Lautner met on the set of the movie Valentine’s Day, and dated for a few months (from August to November). It’s not a big shock that Lautner became the subject of one of Swift’s songs, so maybe she was just dating him for “research.”


5 Courteney Cox

Jennifer Aniston and Courteney Cox are arguably the most famous BFFs in Hollywood. However, they may not have been as close in the mid-1990s, when Aniston dated Counting Crows founder Adam Duritz. The relationship didn’t last long, but it may have something to do with the fact that Duritz started developing a crush on Courteney Cox. He wrote a song for Cox, and apparently it worked, because the two began a relationship soon after she heard the song. These days, Aniston is married to Justin Theroux, and Cox, who divorced David Arquette a few years ago, is in another serious relationship. Adam Duritz, on the other hand, is still looking for love, and allegedly has a Tinder profile.

4 Drake

Drake and Chris Brown definitely “started from the bottom” in terms of their friendship, but now it seems they’re on good terms. One of the reasons Brown and Drake didn’t get along is because Drake dated Rihanna, who is Brown’s ex. Chris Brown stated during an interview with Hot 97, that Rihanna started a relationship with Drake to get back at him. Drake and Brown even got into a nightclub brawl over the singer. Eventually, Chris Brown and Drake were able to patch things up and started collaborating in the studio. It also seems like Rihanna and Chris Brown are done for good, since Brown got himself into all that Karreuche Tran-related drama and has a baby girl with a woman he had an affair with while with Tran.

3 Lindsay Lohan

It’s been a while since Hilary Duff and Lindsay Lohan were good friends, and it has a lot to do with the fact that Lohan stole Duff’s boyfriend. In 2003, the two actresses were involved in a pretty serious feud over singer Aaron Carter. Carter ended his relationship with Hilary, and Lindsay was seen with him not long after the breakup. Aaron admitted to all of this, saying, “I started dating Hilary Duff on my 13th birthday. I was dating her for like a year and half and then just got a little bored so I went and started getting to know Lindsay Lohan, dating Lindsay.” To be fair, they were young, and that’s about the only time this jerk-like behavior is acceptable. Now that they’re all grown up, there have been reports that Aaron wouldn’t mind getting back with Hilary again, but we’re pretty sure she’s not interested.

2 Wiz Khalifa

Rapper Wiz Khalifa has made it clear that he wants to be on good terms with Kanye West, and even stated that he wanted their children to go on play-dates when he was married to West’s ex, Amber Rose. Rose filed for divorce from Khalifa in 2014, and has stated that while she’s still in love with him, he’d turned into a different person. Kanye West even stated that he respected Wiz in his song “Theraflue.” It’s probably a good idea for Wiz to keep a drama-free relationship with Kanye. After all, this congeniality could turn into a musical collaboration one day.

1 1.Kristen Stewart


Kristen Stewart and Rob Pattinson had what looked like a dramatic, enviable and whirlwind real-life romance while they were filming the Twilight movie franchise. However, Nikki Reed and Rob Pattinson had a thing, and apparently Reed and Stewart were friends. At the time though, Kristen was dating Michael Angarano, but the relationship was short-lived. After the first Twilight film was released, Pattinson and Stewart became a couple and their romantic pairing became one of the most popular in Hollywood. However, there are still some conspiracy theorists out there who think that Kristen and Rob were just a couple for the cameras. After all, Stewart is dating a woman now.



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