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Top 10 Celebrities Who Can Never Stay in a Relationship

VO: Lisa Yang
Script written by Nicole Newby These celebs are notorious playboys and are always in the spotlight for having a new partner. Some of these singers may sing about love but they sure can’t stay in a relationship! Justin Bieber, Taylor Swift, Leonardo Dicaprio, Britney Spears and Lindsay Lohan are some of the celebs whose status is always single.

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Top 10 Celebrities Who Can Never Stay in a Relationship

Whether they’re playing the field or simply scared of commitment, these celebs can’t seem to do the whole “long-term” thing. Welcome to MsMojo, and today we’ll be counting down our picks for the Top 10 Celebrities Who Can Never Stay in a Relationship.

For this list, we’ll be looking at celebrities who, for one reason or another, have had a hard time holding down a relationship.

#10: Drake

He may have started from the bottom, but Drake has certainly risen to the top, both in the music industry and the celebrity dating game. From Rihanna and Zoe Kravitz to Jennifer Lopez and tennis star Serena Williams, this guy has no problem picking up some of the world’s most beautiful women… it’s holding on to them that appears to be the difficult part. Perhaps the reason Drake can’t seem to hold down a relationship is his tendency to put all his feelings into lyrics. Or maybe he just likes the playboy lifestyle. Either way, whoever ends up domesticating this Canadian hip-hop star is one lucky gal.

#9: Paris Hilton
Socialite and celebrity heiress Paris Hilton has made a career out of the trifecta of being beautiful, rich and having a famous name. The great-granddaughter of Hilton Hotels founder Conrad Hilton, Paris grew up in a world most people can only dream of. Could this otherworldly upbringing be the reason that she struggles to maintain long-term relationships? We’ll likely never know, but we can say with certainty that she’s made an honest attempt at finding Mr. Right. From actors and musicians to models and baseball players, Paris has dated from all ends of the spectrum. She even dated a Greek Shipping industry heir who had the same first name as her!

#8: Joe Jonas
Of the three Jonas brothers, there’s little argument to be made against the fact that Joe has been the biggest playboy over the years. After flings with Taylor Swift, Demi Lovato, and actress Camilla Belle, the singer went on to date model Gigi Hadid. He clearly has what it takes to attract both beautiful and talented women. It’s hard to imagine what woman wouldn’t want to date this dark and handsome heartthrob. Joe Jones is still a relatively young man however, so perhaps the future will provide a little more emotional stability. Only time will tell!

#7: Katy Perry

While she may have broken through with a song about “kissing a girl.” this singer is clearly more into dating hunky men. Over the years Perry has been with a number of notable guys, including Gym Class Heroes frontman Travie McCoy, actor Russell Brand, singer John Mayer and Orlando Bloom. The problem with each of these relationships is that they didn’t last. It probably doesn’t help that she is constantly on tour or in studio furthering her career as one of the world’s most successful pop star. While she may have difficulty maintaining a relationship, her taste in men is definitely on point.

#6: Lindsay Lohan

To say that this actress has had a tumultuous career would be a bit of an understatement. Her decline into addiction and numerous stints in rehab have been well documented over the years. Perhaps that is why she has struggled to maintain a healthy relationship. While she’s dated a number of different celebs including Aaron Carter and Wilmer Valderrama, and was even engaged to Russian millionaire Egor Tarabasov, none were seemingly meant to last. In fact, the last one was downright volatile. While she is allegedly sober, it will take more than that for her to achieve a consistent relationship status. Here’s hoping the next one sticks!

#5: John Mayer

Where do we begin when it comes to this playboy’s little black book? Mayer has been womanizing since the early 2000s when he dated Vanessa Carlton, Jennifer Love Hewitt and Jessica Simpson. Since then the singer has been linked to a variety of women including Jennifer Aniston, Taylor Swift and Katy Perry. Unfortunately for Mayer, none of these relationships managed to last longer than a few years. It makes you wonder what the problem is… maybe it's the innappropriate post-breakup comments he tends to make. Or maybe “forever” just isn't in his vocabulary.

#4: Britney Spears

Few pop stars have managed to stay in the spotlight for as long as Spears. Ever since she burst on to the scene in the late ‘90s, she has consistently been one of the most popular singers on the planet. However, all of her success has come at the expense of putting her personal relationships under the public microscope. Beginning with her iconic relationship with Justin Timberlake, Spears has gone on to date, and occasionally marry, a bevy of different men. The one thing they all have in common is that the relationships didn’t last. Perhaps the future will be a more stable place for Britney.

#3: Justin Bieber

The days of Bieber and Selena Gomez locking lips are long gone, but the male pop singer has had little trouble finding ladies to fill the void since their breakup in 2014. Bieber has dated or been linked with a slew of different women including Sofia Richie, Chantel Jeffries, Hailey Baldwin and Kourtney Kardashian. Whether it’s his busy lifestyle or simply a desire to play the field, Bieber hasn’t been able to maintain a long-term relationship since Gomez. Perhaps he is attempting to cement his legacy as a playboy? Who knows? Either way, it’s only a matter of time before we see Bieber arm in arm with another beautiful lady.

#2: Taylor Swift

Whether you keep up with pop culture or not, you’re surely familiar with this iconic pop star, and have most likely heard whispers concerning her penchant for dating and then breaking up with the world’s hottest guys. Or... to put it in Taylor Swift’s own words. With actors such as Tom Hiddleston and Jake Gyllenhaal, and musicians such as the likes of John Mayer and Harry Styles to her name, there’s no denying that Swift has dated some of the most desirable men in Hollywood. Where do these romances go wrong? That’s hard to say… but hey! At least we keep getting catchy breakup songs as a result!

#1: Leonardo DiCaprio

DiCaprio has all the characteristics of a playboy: he’s rich, he’s famous, he’s incredibly good-looking and he clearly has a knack for seducing beautiful young women. Over the years, his affinity for dating the world’s top models has been well documented. After Kristen Zang in the ‘90s, DiCaprio would go on to date Gisele Bündchen and Bar Refaeli in the aughts. Since 2010, Toni Garrn and Kelly Rohrbach have been the two big names added. While this might make him the envy of many, the fact remains that DiCaprio can’t seem to maintain a steady relationship. Then again, Clooney settled down eventually - maybe Leo’s time will come too.


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