Relationships can be tricky sometimes. This is especially true if you’re a celebrity. After all, it’s no secret that some famous people form pretty close bonds, and many of these celebrities have mutual friends. So, it’s only a matter of time before someone becomes romantically interested in a friend who used to date another friend. Sure, this can happen with “regular” people as well. However, celebrities often have to keep in mind that their relationships can help to make or break their careers. In some cases, the person who can take a celeb’s career to the next level may be the ex of a friend.
At first glance, it’s pretty safe to say that dating someone that your friend used to date can be weird. That hasn’t stopped some celebrities from giving it a go, and surprisingly, this trend hasn’t ruined too many friendships (that we know of). It’s also important to keep in mind that going on a few dates may not be as serious to celebrities as it might be to someone who isn’t famous. Maybe that’s why celebrities can be exes, yet still be friends, and even encourage their friends to date each other’ exes—if that makes any sense. Here are 12 celebrities that are cool with their friends dating their exes.
12. Kate Hudson
The beautiful and talented Kate Hudson has had her share of Hollywood relationships. After all, she’s charming and adorable, so what man wouldn’t want to date her? She and her friend Cameron Diaz, clearly have similar taste in men, since they both dated baseball player Alex Rodriguez. Kate and Alex were a pair in 2009, and dated for less than a year. The following year, Cameron Diaz was seen leaving Rodriguez’s home with an overnight bag. Even though she and Cameron dated the same guy, Kate doesn’t seem to have a problem with it.
11. Miley Cyrus
Miley has been in the news a lot in recent years for her constant attempts to remind the world that she no longer wants to be thought of as Hannah Montana anymore. She’s hosted Awards shows, worn next to nothing on the red carpet, and basically made it a point to say outrageous and inappropriate things. Cyrus also dated Joe Jonas back in the day, but it seems like she’s been fine with him moving on for quite some time. Miley and Selena Gomez were friends from their Disney days, and it appears Cyrus was cool with Selena and Joe dating. However, the relationship didn’t last long, and maybe Miley was so understanding because she had a feeling it wasn’t going to turn into anything serious.
10. Drew Barrymore
Drew Barrymore was in a relationship with Fabrizio Moretti for a while, but the couple decided to call it quits in 2007. Five years later, comedienne and actress Kristen Wiig started dating Moretti, and Drew was actually happy for her. Barrymore described the situation as “wacky and incestuous,” but stated that she was very happy for her friend. Perhaps Drew realized that Moretti may not have been a good match for her, but he definitely made her friend happy, and that’s all that matters, right? Kristen and Fabrizio are no longer together, but it seems that the two are still close friends.
9. Nikki Reed
Nikki Reed and her friend, fellow actor Ashley Greene, both starred in Twilight. But that’s not the only thing the two actresses have in common. They’ve also got similar taste in men. Both Greene and Reed dated Ryan Phillippe, the actor formerly known as Reese Witherspoon’s husband. Nikki and Ryan dated briefly a few years back. Well after their relationship was over, Phillippe was seen hanging out with Greene. Ryan and Ashley tried to hide their faces from the paparazzi, but we’re not sure why. Maybe Ashley and Ryan didn’t want Nikki to find out about their date. Maybe they didn’t feel like having their picture taken that night. Perhaps both of those answers are correct.
8. Emma Roberts
Emma Roberts is acting royalty. She’s the niece of Julia Roberts, and currently has a starring role on Fox’s Scream Queens. Dianna Agron is best known for her role on the hit Fox series, Glee. Seems that actor Alex Pettyfer has a thing for blonde actresses who star in Fox shows. If the rumors are true, it’s no wonder that either of the girls broke up with Alex. Sources say he was very paranoid, and wanted to check Dianna’s phone often to make sure she wasn’t cheating. Pettyfer and Roberts got into their share of disagreements as well. It seems as though these girls realized that their friendship was more important than a guy.
7. Taylor Lautner
Taylor Lautner and Lily Collins were a couple in 2011 when they starred in Abduction together. Then, like clockwork, the pair called it quits a week before the Los Angeles movie premier. Of course, this created more of a buzz around the movie. The following year Collins met Campbell Bower while filming The Mortal Instruments: City of Bones. Before Christmas of 2013, the couple was no more. Lautner and Bower are friends, and maybe part of the reason Taylor didn’t seem to mind that his friend was dating his ex is because “relationships” can sometimes serve as marketing tools in Hollywood.
6. Hilary Duff
Hilary Duff got her start on the Disney Channel as the adorable Lizzie McGuire, and she’s appeared in her share of movies over the years as well. Back in the day, Hilary and singer Aaron Carter were an item. Carter later stated that he wanted to start dating Lindsay Lohan because she seemed more interesting. Everyone’s a little older now, and it’s pretty safe to say that Aaron is glad he broke up with Lindsay before she got too out of hand. Lohan and Duff had their beef for a while, but they eventually got over it.
5. Kanye West
Rapper Wiz Khalifa has stated that he wants his children to go on playdates with Kanye West’s kids. That can serve as a great way to network and bounce ideas off each other. Not to mention, Kanye’s daughter North and Wiz’s son Sebastian, are both pretty adorable. However, things didn’t quite go as planned. Wiz was married to model and actress Amber Rose, who happens to be Kanye West’s ex. Rose and Khalifa are no longer husband and wife, but that doesn’t mean their kids can’t be friends. Looks like Wiz realizes that he could make some serious moves in the music industry with a guy like Kanye for an ally.
4. Nina Dobrev
Nina Dobrev is best known for starring on the show Vampire Diaries. Fans of the show know that she was in a relationship with actor Ian Somerhalder, but the couple broke up in 2013. They are also one of the few former couples in Hollywood who are seen getting along with each other. Nina is also friends with Julianne Hough. Julianne and Ian dated for a few months, but it didn’t turn into anything serious. The fact that Nina was so cool with Julianne dating her ex is likely an indication that she is completely over the relationship.
3. Heather Locklear
Heather Locklear and rocker Richie Sambora were married for years before Locklear filed for divorce in 2006. That same year, actress Denise Richards started dating Richie. Heather and Denise had also been friends for years, but had some issues in their relationship, which is why many people think Richards decided to go after Locklear’s husband. Denise claims that she and Heather weren’t speaking at the time, which should have meant that dating her ex was off limits. Locklear tried to appear unfazed, but we’re not sure how sincere that was. Then again, Hollywood works a little differently than the rest of the world, and sometimes actors have to do certain things to get noticed.
2. Jennifer Aniston
Jennifer Aniston proved that she and Courteney Cox really are best friends. Musician Adam Duritz was Aniston’s beau for a while, but when the relationship didn’t work out Duritz and Cox became an item. After the Counting Crows band member broke up, he wrote a song about Courteney Cox. Clearly, everyone involved in this story has moved on, but we’re not sure we would have been strong enough to handle the otherwise strange situation with grace and dignity. Cox and Aniston are arguably the most famous pair of friends in Hollywood, and Adam has reportedly taken to Tinder to find love.
1. Taylor Swift
Taylor Swift is known for using her relationships as material for writing songs. Swift has also stated that she doesn’t see a problem in dating a friend’s ex. Taylor and Joe Jonas were an item, even after Jonas dated Selena Gomez, a good friend of Taylor’s. Swift is also friends with Demi Lovato, who also dated Joe Jonas. The song “Forever and Always” is supposedly Taylor’s musical tribute to the relationship, but we don’t hear any lyrics about dating a friend’s ex, so we can’t say for sure. Lovato states that she understands Taylor’s heartbreak and confessed that she and Swift were still friends, even though neither of them is with Jonas anymore.
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