• Wed, Apr 30 - 4:49 pm ET

The 10 Most Heartbreaking Celebrity Friend Break-Ups Of All Time

Lauren Conrad best friend The Hills

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Breaking up is hard to do, whether you’re breaking up with your significant other or with fried foods or with your Netflix subscription. But breaking up with friends can be especially hard. And celebrities aren’t immune to falling out. We sure do love an adorable celebrity friendship around these parts, so seeing them fall apart can be really heartbreaking.

We’ve been hearing a lot about feuds and frenemies as they relate to Selena Gomez recently, so let’s take a moment to look at some of the saddest celebrity friend break-ups, starting with Selena’s. Some of these pairs have since made up or at least tolerate each other, but for some there may be no hope left. Excuse me while I wipe away this tear.

1. Selena Gomez and Taylor Swift

Selena Gomez and Taylor Swift Hope for Haiti Los Angeles California January 22 2010

(Photo: WENN)

The latest reports about these two say that Selena is trying to remove negative influences from her life, which she’s showing by symbolically unfollowing people on Instagram. One of the people she reportedly doesn’t want to talk to is Taylor Swift, who’s apparently trying to get through to her. Come on, you two, make up! Award shows won’t be the same without you sitting together.

2. Selena Gomez and the Jenners

Selena Gomez Kendall Jenner Kylie Jenner 2014

(Photo: Instagram)

This was quite the quick friendship. Selena recently started hanging out with Kendall and Kylie at events like Coachella, but then they became the victims of her unfollow spree. There are rumors it’s because of Justin Bieber (and when isn’t it?), and the Jenners are supposedly firing back by calling Selena the bad influence. This should be interesting.

3. Selena Gomez and Demi Lovato

Selena Gomez Demi Lovato selfie

(Photo: Instagram)

Oh, Selena. What are we going to do with you? These two seem to be doing okay now, and even FaceTimed with Taylor Swift recently (before that supposed feud happened). But a few years ago things weren’t so pretty. Demi Lovato’s relationship with Miley Cyrus was allegedly involved in the rift.

4. Demi Lovato and Miley Cyrus

Miley Cyrus and Demi Lovato April 2009

(Photo: WENN.com)

Speaking of Miley Cyrus, she and Demi also had a break-up of their own. They were friends a few years ago, both being Disney starlets and all, but they’ve had a rocky relationship. Just last month they unfollowed each other on Twitter, so that could be the nail in the coffin.

5. Katy Perry and Rihanna

Rihanna Katy Perry MTV Video Music Awards 2012

(Photo: WENN.com)

These two were thick as thieves a couple of years ago, probably because they could bond over their ever-changing hairstyles. But reportedly Rihanna’s reunion with Chris Brown didn’t sit well with Katy — or the rest of us, honestly. They were spotted out together recently, so it looks like things might be better.

6. Paris Hilton and Nicole Richie

Nicole Richie Paris September 2004

(Photo: WENN)

Classic frenemies. They were everyone’s least favorite socialite pals. They starred on a reality show together and showed off how spoiled they both were. How could they possibly drift apart? In 2005 Paris declared that they weren’t friends anymore, and the world wept. Last year they were photographed together looking happy, so it seems like they’ve had time to bury the hatchet.

7. Gwyneth Paltrow and Madonna

Gwyneth Paltrow Madonna Tracy Anderson 2008

(Photo: WENN)

See how trainer Tracy Anderson is between Madonna and Gwyneth in that photo up there? Well apparently she also came between their friendship, too. Tracy and Gwyneth are still close and own gyms together, but they both fell out with Madonna. And Gwyneth even recently said she has better abs! The horror!

8. Gwyneth Paltrow and Winona Ryder

Winona Ryder and Gwyneth Paltrow New York City

(Photo: WENN/Sidewalk)

Oh, Gwynnie. You’re such a frenemy. Back in the 90s she and Winona were total pixie cut pals. But when Gwyneth got the lead role in Shakespeare in Love and Winona didn’t, and when Gwyneth won an Oscar for that role, things are rumored to have gone bad. Gwyneth even wrote about a frenemy on GOOP, and many suspect she was expressing happiness over Winona’s shoplifting fiasco.

9. Lauren Conrad and Heidi Montag

Lauren Conrad and Heidi Montag 2006

(Photo: WENN)

Remember when these two were friends on The Hills? And then remember when Spencer Pratt happened? And remember all of LC’s mascara tears? And remember when she lurked at Heidi’s wedding in that really dramatic scene? God, I really want to watch The Hills now.

10. Katie Holmes and Victoria Beckham

Victoria Beckham Katie Holmes Paris 2006

(Photo: Tom McGourty/WENN)

Remember when Katie and Victoria were fashionable BFFs, and when Victoria attended TomKat’s wedding and everything? Sometimes thing just don’t work out. Rumors say they fought over everything from Scientology to parenting.

You can reach this post's author, Jill O’Rourke, on twitter.
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