Alone Again! 18 Constantly Single Celebrities

Dating is hard but it's even harder when you're a celebrity. As sad as it may sound, celebrity relationships rarely work out. After all, when you're constantly under a microscope, chances are your relationship won't be easy to maintain. RadarOnline.com has collected a list of constantly single celebrities. For one reason or another, these 18 celebrities have not been able to keep a relationship going. Whether it's infidelity, a busy schedule or those pesky irreconcilable differences, these stars have loved and lost several times.

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Everyone knows about the rocky relationship between Justin Bieber and Selena Gomez. But they're not alone in their bumpy quest for love. Some of Hollywood's most famous faces have come up short when it came to finding the right person. Celebrity relationships are always good for a headline, especially since they don't always last.

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Taylor Swift has practically made a career out of her relationship troubles. Some of her most popular songs have been about failed relationships.

Ever the bachelor, Leonardo DiCaprio has constantly surrounded himself with different models and actresses over the years. While Gisele Bundchen and Bar Refaeli managed to hang on to him for five and six years respectively, the Oscar winning actor never settled down.

Selena Gomez's love life was filled with drama. From an on and off again relationship with Justin Bieber, to a 10 month romance with The Weeknd, Gomez's romantic entanglements have been nothing short of exciting.

Bieber has been the one that just keeps coming back to Gomez, but he also had himself a few flings in between breakups with the singer, including Hailey Baldwin and Sofia Richie.

Kardashian/Jenner paramours have been a who's who of rappers and athletes. But Kourtney Kardashian's most notable man has been her on-again-off-again boyfriend, Scott Disick. Despite three kids and a long shared history, Kardashian never tied the knot with Disick.

Chris Brown and Drake's names have always come up when discussing Rihanna's love life. But neither beau was able to hang on to the pop superstar.

Madonna's gone down the isle twice during her career. Her first marriage came in 1985 to Sean Penn before divorcing in 1989. She tried marriage once again with director, Guy Ritchie before divorcing yet again in 2008 after eight years of marriage.

John Mayer may not come off as a bad boy based on his music, but he's broken quite a few hearts—notably those of Katy Perry and Swift.

Perry dabbled in matrimony when she shacked up with comedian Russell Brand in 2010 for a marriage that lasted all of 14 months. But the pop star has rarely committed to a long term relationship since then.

Chris Pine has been notoriously private about his personal life, but the Star Trek actor has been linked to various flings with notable women including Audrina Patridge and Zoe Kravits.

Michael B. Jordan may have enjoyed his single life, but the actor admitted that one of his greatest fears was to grow old alone. He's not a player, he's just cautious!

Comedienne, Chelsea Handler has avoided being tied down. In fact, she revealed that she doesn't keep in touch with any of her exes and doesn't see the appeal of it.

Michelle Rodriguez admitted that she "couldn't last more than six months with somebody." The self proclaimed "lone wolf" couldn't last with notable names such as Zac Efron and Cara Delevingne.

No one has been able to put a ring on Charlize Theron's finger. Sean Penn was oh so close, but the Oscar winning actress broke that off after a year and a half of dating.

Delevingne's name has been linked to the likes of Harry Styles and Paris Jackson. But outside of her 18 month relationship to musician, Annie Clarke, the actress/model has remained single for the most part.

Simply standing next to Harry Styles could create relationship rumors. But outside of relationships with Swift and Kendall Jenner—who he may or may not have cheated on— the former One Direction singer has stayed consistently single.

Halle Berry just hasn't been able to catch a break when it comes to love. So much so that she effectively gave up on love altogether. That's understandable considering her three divorces.

Britney Spears has shown that she's a strong, independent single mom who doesn't need a man! Since her divorce from Kevin Federline, the pop star has managed to stay single while raising their two kids.

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