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25 Celebrities Who Failed at Dating

Jennifer Aniston

We love Jennifer Aniston, and she always be No. 1 in our hearts, but she clearly wasn’t No. 1 for a lot of famous fellas. Brad Pitt dumped her for Angelina Jolie, and Jennifer has also been left by the likes of Vince Vaughn and John Mayer. She’s now married to Justin Theroux, so maybe this time will be the one that sticks!

Jennifer Lopez

J. Lo is the second Jennifer on our list who can’t seem to find love. She’s been married and divorced three times: first to Ojani Noa, then to Cris Judd, and most recently to Mark Anthony. She came very close to marrying Ben Affleck, but he practically left her at the altar. We’ve heard she’s a bit of a control freak, and most men tend not to like that attribute. She’s still more beautiful than most 20-year-olds, so she still has a lot going for her! 

Demi Moore

Demi is the ultimate cougar. She knows she’s still got it, so she dates men who are significantly younger, even though those relationships tend to fizzle out pretty quickly. She’s been with Ashton Kutcher, Leonardo DiCaprio, Anthony Kiedis, and Bruce Willis. Her most recent paramour was Vito Schnabel, who is the 20-something son of director Julian Schnabel.

Katy Perry

Katy Perry was married to Russell Brand for two years before he famously and cowardly dumped her via text. After their divorce, Katy has been spotted with the likes of John Mayer, Robert Pattinson, Baptiste Giabiconi, Robert Ackroyd to name a few. We all know she kissed a girl and liked it, so perhaps she should explore that avenue!

Tom Cruise

Tom is famous for being both the dumper and the dumpee in his relationships. He’s been with Nicole Kidman, Katie Holmes, and Penelope Cruz, and none of those relationships ended well. His looks are definitely not to blame, so maybe it’s his devotion to Scientology that’s scaring the ladies away. 


Rihanna is gorgeous and talented, but hasn’t stuck with the same guy for very long. Her relationship with Chris Brown was the most high-profile (and we’re very glad they’re not together), but she’s also had flings with Ashton Kutcher, Shia LeBeouf, Drake, Andrew Bynom, Matt Kemp, and Josh Harnett. She probably has this bad luck because she only dates one “type” of guy, and that hasn’t really worked out so far.

John Mayer

While John Mayer’s voice and sultry lyrics keep drawing the ladies in, his rude personality keeps pushing them away. He’s dated many famous starlets, including Taylor Swift, Katy Perry, Jennifer Love-Hewitt, Jessica Simpson, Minka Kelly, and Jennifer Aniston. Whew.

Justin Timberlake

Justin is another playboy who has made his rounds in the celebrity world but hasn’t been able to keep anyone around for long. He’s dated some of the biggest stars in Hollywood, including Fergie, Britney Spears, Olivia Munn, Janet Jackson, Ciara, Rihanna, Olivia Wilde, and Jenna Dewan (now Channing Tatum’s wife). 

Adam Levine

The ladies love Adam, and the guys are jealous of him because he’s constantly dating supermodel after supermodel. He’s currently married to Victoria’s Secret Angel Behati Prinsloo, and he’s also dated Maria Sharapova, Janine Habeck, Arielle Vandenberg, Angela Bellotte, and Anne Vyalitsana. There are rumors that things between Adam and Behati are a bit rocky, but none have been confirmed. Maybe they’ll stay together, or maybe one day he’ll be back on the market. Who knows!

Taylor Swift

Taylor is probably the most famous serial dater because she chronicles her dating adventures in her music. She’s dated everyone from Conor Kennedy to John Mayer to Tom Hiddleston. 

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Madonna was married to Guy Ritchie for quite some time, but after they divorced, she began dating young man after young man. Oftentimes, these men are dancers from her tours, which could make for some awkward work encounters. 

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Britney Spears

Britney has seemed to take it a little easier these days, but a few years ago, insiders claimed that Britney jumped from boyfriend to boyfriend more often than she changed clothes.

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Harry Styles

There are always tons of rumors going around about who this former One Direction star is dating, but none of them ever seem to materialize into anything meaningful. He’s been tied to the likes of Taylor Swift and Kendall Jenner in recent years.

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Cameron Diaz

Jennifer Aniston is famous for being perpetually single, but Cameron Diaz has actually been single for longer! She never really gets tied down, although she has dated the likes of Justin Timberlake and Alex Rodriguez.

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Bradley Cooper

Bradley Cooper is rumored to have dated nearly every single lady in Hollywood, from Zoe Saldana to Jennifer Aniston to Suki Waterhouse. These whirlwind romances never seem to get serious, though.

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Seth MacFarlane

Seth MacFarlane, the brains behind Family Guy, American Dad, and Cosmos, has quite a bit of luck in getting the ladies, but not much luck in keeping them around. He’s dated beauties like Emilia Clarke and Charlize Theron, but neither lasted long.

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Charlie Sheen

Charlie Sheen has done it all: fame and fortune, addiction, rehab, jail, you name it. Yet, women are still clamoring to get near him, and well, we’re not surprised that he doesn’t turn them down!

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Lil Wayne

Lil Wayne has dated quite a few women and has had children with four of them. He doesn’t ever seem to hold down those relationships for very long, though, but he somehow keeps managing to find new, beautiful girlfriends. 

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Joe Jonas

This Jonas brother is known for dating gorgeous, successful women like Taylor Swift, Ashley Greene, and Demi Lovato, but he never manages to keep them around for very long. Who knows who he will date next!

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Ryan Gosling

Ryan Gosling is one of the dreamiest guys in Hollywood, so it’s no wonder that he’s dated a long list of the most beautiful women in Hollywood, including Sandra Bullock, Rachel McAdams, Olivia Wilde, Blake Lively and Eva Mendes. He and Mendes are currently together, so maybe the saga will end with this cute couple! 

Amber Rose

Amber Rose became famous overnight, and nobody's really sure why, other than the fact that she’s dated a lot of celebrities. She’s been linked to Reggie Bush, Ryan Banks, Fabolous, Chris Brown, and Wiz Khalifa.

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P. Diddy

P. Diddy seems to have settled down for now with Cassie Ventura, but he has a history of casually dating many women. Some of these women include: Lil Kim, Sienna Miller, Naomi Campbell, and Jennifer Lopez!

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Nick Jonas

The other Jonas brother who’s famous for serial dating is Nick. This younger Jonas has dated nearly every famous millennial woman, from Miley Cyrus to Selena Gomez to Gigi Hadid.

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Derek Jeter

Derek Jeter likes to play the field both on and off the actual baseball field. He loves dating beautiful women, and they apparently love dating him! (Briefly.) He’s been linked to Jessica Alba, Minka Kelly, Jordana Brewster, and more.

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50 Cent

This famous rapper has children with two women and quite a few other famous, short-term girlfriends--including Paris Hilton, Khloe Kardashian, Ciara, and even Chelsea Handler. He’s never been married, though!

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