16 Successful Stars Who Fail Hard At Relationships

Relationships are tough. They take a lot of time, hard work, and commitment. Some people just do not have the patience for this. Some people have hearts that are just so big, they want to share them with everyone they can. This isn’t limited to us “regular folks.” If anything it happens more often to celebrities. Even with the best intentions, some people can fail at relationships pretty hard. But that isn’t always a bad thing.

Maybe, having so many relationships is just practice for when someone is ready to get it right? Taylor Swift could actually be considered a relationship pro! Who are we to judge? If these celebrity serial daters have one thing in common, it’s that they all can’t help but bounce from relationship to relationship!

1. Leonardo DiCaprio

When you played Jack in the Titanic, how could you not want to keep the romance alive again and again? Being one of the hottest bachelors of the’90s and ‘00s, we don’t necessarily blame Leo here. The man loves his models if Kristen Zang, Bar Rafaeli, Gisele Bündchen, and Erin Heatherton are proof enough! He also was linked to Blake Lively and Rihanna for a time.

2. Katy Perry

Katy Perry has had some pretty bad breakups, so we can’t really blame her for failing at them. Her divorce from Russell Brand was painful for everyone to watch. Then there was her on-again-off-again relationships with celebrity player John Mayer and Orlando Bloom. She also randomly dated Diplo for just under a year.

3. Zac Efron

It might be years since Zac and Vanessa Hudgens broke up, but we think all the women he’s been linked to since they probably can’t compare to his High School Musical love. In fact, it seems like this Baywatch actor won’t really commit to anyone! *Desperately wishes we could be the one to change that*

4. John Mayer

John has had many lovely women in his life, which comes as no surprise as he’s known for crooning out some heartfelt music. Then again, he’s kind of been known as a player. Exes like Jessica Simpson, Taylor Swift and Jennifer Aniston aren’t exactly his biggest fans. Especially after he spilled some seriously TMI information about how Jess was in the bedroom, she flipped. And we all know who Tay’s “Dear John” is about…

5. James Franco

Back in his Spider-Man days, James was a pure hunk. As of recent years, he’s been known more as a stoner dude, sometimes-serious-actor-turned-professor. But in his career since the early ‘00s, he’s dated a handful of famous folks, some rumored and others confirmed, like Emilia Clarke, Lana Del Ray, Amanda Seyfried, and more. There also was that time he was exposed for being thirsty AF in an underage girl’s DMs.

6. Bella Thorne

Since her Disney days, Bella has been linked to a number of famous folks. One of her most public relationships being with fellow Disney star, Gregg Sulkin, but once they broke up, it seemed like she was with someone knew every second. She briefly dated Tyler Posey post-breakup, then was accused of cheating on him with Charlie Puth. She was linked to Blackbear, Scott Disick and YouTuber Tana Mongeau, within the past few months as wel.

7. Lil Wayne

Over the course of his lengthy rap career, Lil Wayne has been linked to many women, starting with his childhood sweetheart, Toya Wright. He apparently dated Meagan Good way back in the day. He’s got four children by four different women and while everyone swears he and Nicki Minaj have been an item, Nicki adamantly denies this. But who knows what can happen in the future?

8. Justin Bieber

Justin Bieber was one half of a relationship we all rooted for at first and then watched it go down in flames. Since his very public breakup with Selena Gomez, the Biebs has been linked to quite a few ladies, but the hole Selena left in his heart seems a tough one to fill. We all hoped he’d find happiness like she has! That’s when we suddenly found out about him and Hailey Baldwin!

9. Scott Disick

Is it any surprise this Kardashian baby daddy is on the list? For years we watched him work out his issues with Kourtney Kardashian, but ultimately they split (after his struggles with alcohol addiction and fidelity seemed to get the best of him) and Scott’s been linked to many ladies since then. Most recently, he was spotted with Bella Thorne, and now Nicole Richie’s little sister, Sofia… all who are significantly younger than he is.

10. Lucy Hale

Did you know Lucy Hale dated Disney Channel star David Henry back in 2007? She’s has had quite a few romances since then including Paul Iacono, Chris Zylka and most recently, she split with musician Anthony Kalabretta.

11. Ariana Grande

We all loved her with Mac Miller, and now with Pete Davidson but her road to romantic bliss was not an easy one. Since her days as a Nickelodeon star, Ariana Grande has had a handful of famous men in her life. While she and Big Sean had a pretty public breakup, it was also a relationship that apparently started while he was still with Naya Rivera. She’s also dated Nathan Skyes of The Wanted

12. Ed Sheeran

For a man known for singing about love, Ed Sheeran has had his share of female companions. He admits he has issues with dating, which might explain some of his songs. His problems with Ellie Goulding were made pretty public in the song “Don’t.” But hopefully, his relationship with current girlfriend Cherry Seaborn goes much better!

13. Harry Styles

Harry Styles is one of those celebrities who will basically deny dating anyone, even if he’s caught mid-kiss with them. But with famous exes like Taylor Swift and Kendall Jenner, it’s hard to deny. He’s a ladies man, but doesn’t that almost come with his kind of fame?

14. Nick Jonas

As a famous boy bander, it’s no surprise Nick has been linked to many beautiful women. Honestly, who HASN’T Nick Jonas dated? From Kate Hudson to Camila Cabello, Tinashe, and Kendall Jenner… and that’s just SINCE his breakup with Olivia Culpo. Many fans think his relationships with people like Olivia, Miley Cyrus, and more never worked out because he’s secretly meant to wind up with his BFF, Demi Lovato.

15. Joe Jonas

Joe Jonas might be engaged now, but he can’t escape this list. We think if anyone can turn this man around, it’s Sophie Turner. But his messy affairs with Taylor Swift, Demi Lovato, and Gigi Hadid are hard to forget.

16. Taylor Swift

Does Taylor fail hard at relationships, or is she winning? With famous flames like Taylor Lautner, Joe Jonas, Tom Hiddleston, and more, Taylor’s has plenty of ammo for all her break-up songs. She’s had enough relationships to sell albums for the next decade. We really thought the fling with Calvin Harris would last — but sadly, it did not.

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