BFFs No More: 15 Surprising Celebs Who Openly Dated Their Friend's Exes

Whatever happened to steering clear from your friend's ex? What happened to the loyalty to friendship and the shame around dating someone who your friend dated? Is that all just out the window now? Hollywood is a cesspool of foolishness. Because a lot of these friendships are for convenience and hold no real value, it’s easy for overlap to occur in their dating world. No one feels like they are doing something wrong because it's a hard dating life out there. Can you blame them?

It’s hard to maintain friendships when your life consists of long work hours and never being in one place for too long. That is also the reason why a lot of these relationships fall apart. That being said, like the normies of the world, celebrities also read tabloids and catch up on their entertainment news. It’s not like they are completely oblivious to who is dating who and who broke up when. So they are clearly making a conscious decision to date someone who they know was their “friend's” ex. It’s hard to be too annoyed with them though, as big as Hollywood is it’s actually quite small. You go to the same parties, certain groups run into one another all the time and there really is no way for them to avoid each other. Well unless they decide to not go out which we all know is impossible for a celeb. It’s actually a part of their job. You will notice that some of the celebs on this list show up more than once, that is saying a lot. Here is a list of some weird love triangles that will make you question the definition of friendship.

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15 Taylor Swift, John Mayer, Katy Perry

via Urban Asian

Taylor Swift and Katy Perry were actual friends. They hung out together, they partied together, Perry was low-key a part of Swifty’s squad. These two had a real friendship. Back in December 2009, Swift started dating John Mayer. The couple was very public and there was no denying that this was a real relationship. It was in the beginning stages but there was a spark. Unfortunately, by February 2010 the budding relationship fizzled out and Swift and Mayer went their separate ways. In 2012, Perry was spotted holding hands and cuddling with Mayer. Fans immediately buzzed about the relationship and quickly pieced together that she and Taylor are friends and now she is dating Taylor’s ex. It was a slap in the face for sure but by this time Taylor had already written a song about Mayer basically being a bad boyfriend. She titled it “The Cut”. However, by 2014, their friendship had taken a wild turn, instead of exchanging pleasantries on social media and cat memes they were sending out cryptic messages about bad friends and stealing dancers. The two are no longer friends and we would like to believe it is not because of Mayer dating both of them. Unfortunately, during arguments that fact has probably come up at least once or twice.

14 Nina Dobrev, Ian Somerhalder, Nikki Reed

via E!

Nina Dobrev and Ian Somerhalder dated for a very long time basically the entire time that they were on Vampire Diaries together. Most of their fans thought that they would definitely get married and have gorgeous little raven-haired babies. Wrong! They instead broke up leaving the world to wonder ‘does anything in the entertainment world last?’ Soon after their break up Somerhalder met Nikki Reed and the couple were not afraid to hide that they were dating. However, people believed they should have kept things more under wraps seeing as Dobrev and Reed were actually friends. Fans were unhappy by Somerhalder’s poor choice and accused him of ripping two friends apart. Rumors flew around about Dobrev being beyond pissed at her ex and a girl she considered a friend. In an effort to squash what Somerhalder alluded to as a fake beef the threesome posted a picture of them out to dinner and in the caption, he said this was their first real dinner. However, you can’t school the fans on your own life that’s for sure. His page was bombarded with photos of the girls hanging out LONG before they even knew Somerhalder; dinners, parties, coffee dates you name it. So we can officially call Reed a bad friend.

13 Emma Roberts, Alex Pettyfer, Dianna Agron

via Popsugar

In 2008 before Emma Roberts was in an on again, off again relationship with Evan Peters she dated up and comer Alex Pettyfer. He was the new bad boy of Hollywood and it was a relationship that everyone was questioning. It didn’t last very long under a year to be exact and the two went their separate ways. In 2010 Dianna Agron met and quickly started a relationship with Pettyfer so quick that the couple only dated for about a year and during that year they became engaged. What was crazy was she and Roberts were friends and let’s be honest no one wants to cross Roberts she can be a little cuckoo. Thankfully, Roberts didn’t seem to care even though she counts Agron as a friend it’s not like they were the best of friends. Roberts probably didn’t care because maybe she knew how crazy he was. Agron and Pettyfer ended up having a horrible break up one that the tabloids could not stop talking about. Everything from abuse allegations to him throwing temper tantrums. Agron got the heck out of dodge real quick. Now she is married and Roberts is engaged and Pettyfer ruined his career with his bad attitude.

12 Selena Gomez, Taylor Lautner, Taylor Swift

via Zimbio

For the second time, Taylor Swift is making our list she just can’t stay away from a love triangle. It really isn’t her fault she just loves attention no matter which way it comes. This time it included Selena Gomez and Taylor Lautner. Remember when Taylor and Taylor was a thing? Everyone thought it was so cute and so fun that two people with the same name could be in a relationship. Unfortunately, just before these two lovebirds were a thing, Lautner was in a relationship with Selena Gomez. Gomez used to be a great friend to Swifty, once upon a time she was apart of that clique that Taylor loves to have behind her. But like many of her girlfriends, Gomez low-key jumped ship when she realized how toxic Taylor is but that’s a whole other story. The timeline for this relationship and their friendship breaking down is a little iffy mostly because Gomez could care less to talk about it. She seems pretty unphased by Taylor's actions we assume that could mean two things. One, she expected Taylor to do something shady like this or two, she is trying to live in the positive and let that garbage slide off her back. It’s probably a bit of both.

11 Naomi Campbell, Leo DiCaprio, Rihanna

via starmagazine.com

Leo DiCaprio loves himself a beautiful woman, usually, she is a model but for some reason, Rihanna caught his eye and was able to bend his rules a bit. However, before Rihanna, he dated model Naomi Campbell briefly we all know DiCaprio doesn’t stay in relationships for long so as soon as it began it was basically over. However, since Rihanna had blown up into this mega star she has been able to call Campbell a good friend. One would assume that she would have to know that DiCaprio was her boo back in the day. But whether she knew or not in 2015 she took her shot at a relationship with the actor. The two women have no love loss probably because they are so secure within themselves and know that they are both gorgeous chicks. That being said, we have to wonder if they ever got together and traded stories about their time with DiCaprio. They have both since moved on with RiRi dating Hassan Jameel a Saudi businessman and DiCaprio onto whatever model he is onto now. Campbell has even moved on to date rapper Skepta and even did a naked photoshoot for GQ with him. Everybody’s happy.

10 Miley Cyrus, Nick Jonas, Selena Gomez

via Hollywood.com

This love triangle has to be one of the most dramatic on our list. It made headlines for over a year mostly because the people involved were not afraid to talk about what was going on. Well more like take cryptic social media jabs at one another. Nick Jonas admitted to dating both Selena Gomez and Miley Cyrus at the same time on and off for a good while. This was back when all of them had hit shows on Disney. It was normal for them all to be seen in public together because they could have just been filming a crossover episode or whatever else Disney wanted them to do. The girls were as confused as Jonas was when it came to their relationship status. Demi Lovato let it slip during an episode of Carpool Karaoke with James Corden (and Jonas joined her) that Jonas would go back and forth between each girl essentially when he was bored with one he would go to the other. The only question we have is when was Cyrus ever boring? She strikes us as someone who could keep anyone on their toes even during her good girl phase on Hannah Montana. We always knew that Nick Jonas was a bit of a playboy.

9 Joe Jonas, Gigi Hadid, Zayn Malik

via Daily Mail

In December 2015, Joe Jonas unfollowed his ex-girlfriend Gigi Hadid on Instagram. This was clearly a sign of great trouble when an ex well when anyone unfollows someone on any social media platform it’s a problem. The unfollowing was supposedly in retaliation to Hadid starting a relationship with former One Direction member Zayn Malik. It must have cut like a knife having someone he was kind of friends with dating his freshly ex-girlfriend. Even though their relationship was a mere 5 months it seems as if Hadid really had her claws in there quite deep. Unfortunately, we have to agree with Jonas it does suck when someone you ended a relationship with just a few short weeks before moves on so quickly. No matter how long the actual relationship was it still burns. Jonas had made a few comments on their relationship like “it’s interesting” or that he was “surprised” at how quickly she moved on. Thankfully, he ended up in a new relationship and stopped brooding over his ex-girlfriend. The nail in the friendship coffin for the boys was when Jonas deleted a picture of himself, Kanye West and Zayn with the caption #SQUAD off his Instagram page. Bitter bones.

8 Bella Hadid, The Weeknd, Selena Gomez

via Entertainment Tonight

Bella Hadid and The Weeknd were the IT couple for a long time. They attended every red carpet event together, they looked stunning together. When they broke up we seriously think people mourned the loss of what their relationship could have been. Eventually, The Weeknd moved on to Selena Gomez and for 10 long months, the world got to see the Weeknd and Hadid take subtle jabs at one another on social media. At the same time, they got to see Gomez slowly pull away from Taylor Swift's squad (that both she and Hadid were apart of). Hadid unfollowed Gomez on Instagram and to be honest we were surprised she didn’t delete every last picture she had of her ex-friend as well. Okay, we are jumping the gun should we refer to them as friends? They were in the same squad but there are so many women in that squad it’s hard to say who actually calls one another friends. In return, The Weeknd and Gomez both unfollowed Hadid on Instagram. It’s just tit for tat with this triangle. Eventually, the couple broke up and The Weeknd was recently spotted in Cannes with Bella Hadid all loved up once again.

7 Nick Lachey, Kim Kardashian, Nick Cannon

via www.choeurdelaradio.org

Even though Kim Kardashian is now married to Kanye West and Nick Lachey is now married to Vanessa Lachey she was one the contention of a small rift between the two friends. Kardashian was dating Nick Lachey in 2006 but the relationship didn’t last long it ended that same year. Lachey later told the press that he was turned off by her social climbing. He even went as far as to say that he believes that she would call the paparazzi and tell them where she and he would be that day. Soon after their break up, she was seen out with a new Nick, Nick Cannon. That relationship ended in early 2007 so it didn’t really have too much of a negative effect on Lachey’s friendship with Cannon. One thing it did affect was how much the guys realized they had in common. They soon found out that they just couldn’t be in a relationship with Kardashian because of how thirsty she was for fame at the time. Cannon eventually broke up with Kardashian because she lied about her adult tape. Currently, the three are in happy places in their lives but their love triangle was bizarre and only proved that they both realized that reality TV love just isn’t for them.

6 Taylor Swift, Joe Jonas, Gigi Hadid

via YouTube

In 2015 Taylor Swift gave her blessing to Gigi Hadid and Joe Jonas when they began dating. She certainly likes to pretend to be the bigger person. Everyone knows that Swifty and Jonas dated back in 2008 for some time and everyone also knows that he supposedly broke up with her during a 27-second phone call. All this of course is according to Taylor and yes, she wrote a song about it. Fast forward to 2015 well after the creation of Taylor’s girl squad. New model Gigi Hadid is seen out more and more with Joe Jonas, of course, this form of betray is out of pocket. The new couple were a hit they appeared everywhere together and fans were obsessed with them. But of course, everyone wanted to know what Taylor thought after all, Gigi was still in her crew and one of her besties. Taylor let it slip to Hollywoodlife.com that she approved of their relationship and moreover, she has no hard feelings towards Gigi (what about Joe though?) she didn’t have to pretend to approve for long because the couple eventually broke up and Hadid moved on to Zayn Malik. 

5 Drew Barrymore, Fabrizio Moretti, Kristen Wiig

via Clevver

This situation proves how cool Drew Barrymore is in every situation. Barrymore dated musician Fabrizio Moretti in 2005 when the relationship fizzled out they parted ways amicably because that’s what adults do. Then in 2012 Kristen Wiig and Moretti were spotted spending some time together. Immediately people wanted to see the drama take place between Barrymore and Wiig seeing as over the years they had become good friends. However, Barrymore squashed the rumor during an interview with Allure magazine. She stated what she truly felt about the relationship between her good friend and old ex. “Knowing them both so well, it is 'fitting'. 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.”. The two eventually broke up in late 2013 but it doesn’t look like they could get over each other. Over the years, they have been spotted enjoying one another’s company and just trying to keep whatever it is under wraps. Oh, and Barrymore still doesn’t give AF because she moved on to get married and have 2 daughters. She and her husband Will Kopelman are now divorced and now she is too busy with 2 daughters to care about anything else.

4 Josh Hutcherson, Zoey Deutch, Avan Jogia

via Oh No They Didn't/Pinterest

In 2012 Avan Jorgia began dating Zoey Deutch girls around the world were jealous AF. So of course when news broke that he had broken the cardinal rule of not dating a friend’s ex people were all over the drama. Who was the best friend they spoke of? It was Josh Hutcherson. It turns out that Hutcherson and Deutch dated from about 2 years before calling it quits. Unfortunately, after 5 years Deutch and Jorgia also called it quits and a few months later she was out with a new mystery man. As for the two friends it doesn’t seem as though they are as close as they used to be. They no longer appear on one another's social media pages, they aren’t out and about with one another anymore. Neither of them have commented on the coincidence or the the fact that they no longer hang out. They could certainly no longer be friends because as people grow up they grow apart but it’s kind of interesting that all this started to happen after Jorgia and Deutch started dating. Let’s be honest it could have also been awkward for her to have her ex-boyfriend as a third wheel.

3 Owen Wilson, Sheryl Crow, Lance Armstrong

via Tportal

Owen Wilson once dated Sheryl Crow from 1999 to 2001. It seemed pretty serious they were together for over a year but unfortunately broke up. Then Crow went on to date Lance Armstrong from 2003 to 2006. They didn’t just date they eventually got engaged in 2005 but broke up around the time of her breast cancer diagnosis. We will let you know right off the bat that there was no bad blood between the boys when they realized that they both dated Crow for a significant amount of time. There are probably two reasons for this; one would be because a lot of the time when men move on it’s like they completely forgot they dated that person. Or two, he was in another relationship and didn’t have the time to care. Regardless, it’s a shady move for a friend to date another friend’s ex there is no questioning that. That being said, it seems like this is a normal thing for these two friends because they have another woman in common. Kate Hudson. The two also dated Kate Hudson and while none of them ended up engaged to the blond beauty they were both in their relationships with her for a significant time. Isn't there a label for guys who make this a regular habit? Just saying...

2 Heather Locklear, Richie Sambora, Denise Richards

via Us Weekly

First of all, this love triangle proves that you are never too old to be immune to ridiculous behavior. Heather Locklear was married to Richie Sambora for well over 10 years. They even have a daughter together, Ava. Unfortunately, the couple divorced in 2006 because Locklear didn’t feel comfortable with how close her husband was getting to Denise Richards. Soon after their messy divorce was finalized Sambora and Richards were out and about in a full-blown relationship. The problem was that Richards and Locklear had been friends for years and good friends at that. They used to double date when Richards was married to Charlie Sheen, their kids would play together. The situation was beyond awkward. Richards and Sambora ended up dating on and off for several years but they too eventually broke up. Locklear however, came out of the whole ordeal looking like the bigger person because she gave the couple her blessing and kept it moving. She even moved on to her own relationship which ended up having its own drama. It may be safe to say that their friendship is donezo which is a shame because all Richards had to do was date someone who wasn’t linked to her good friend. It doesn’t seem like it was worth it in the end.

1 Shania Twain, Robert "Mutt" Lange, Marie-Anne Thiebaud, Frederic Thiebaud

via Daily Mail

This is one of the craziest friendship betrayals we have heard coming out of the entertainment industry. Shania Twain was married to Robert “Mutt” Lange for over 14 years so when news broke that they were divorcing the country world was shocked. They wrote music together, he was there from basically the beginning of her success. It was even more embarrassing for Twain when news broke that he and her very best friend Marie-Anne Thiebaud were in a full blown relationship and they were getting married. Talk about the ultimate betrayal. They are still married currently and Twain also found love with Marie-Anne’s ex-husband, Frederic Thiebaud. The entire situation is awkward and weird and just betrayal after betrayal. It really messed Twain up. She even lost her voice and was forced to take a hiatus from music. Twain has recently been more open about her disgust for her former best friend. During an episode of Watch What Happens Live with Andy Cohen, she stated that she wishes she never met Marie-Anne Thiebaud. We wish the same thing for you, sis.

References: popcrush.com, dailymail.co.uk, stylecaster.com, elle.com, axs.com, newseveryday.com,

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