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10 Celebrities Who Are Unlucky In Love

OMG October 27, 2017 By Hugo

While you may regularly lament your inability to find a partner, it's worth remembering that most people in life are single, and you're not the only one waking up with no one to hold in the morning. 

Instagram/ Windsor Dalton

After all, even the chiseled, tanned faces of Hollywood celebrities find themselves single for longer than they'd probably like so to make you feel better about your single status, here are 10 stars who, probably like yourself, are also unlucky in love. 

1. Taylor Swift

Pop star Taylor Swift has had so many relationships it's almost impossible to keep track of them, such has been their near-identical outcomes. I mean, let's face it, Swift has a knack for writing a good heartbreak song, and as many have said before, she hasn't been afraid to dish the dirt on her exes in the form of winey, saccharine lyrics. 

Shutterstock/ Joe Seer

Just ask the likes of John Mayer, Jake Gyllenhaal, Harry Styles, and Taylor Lautner. And then there are the other, more recently doomed romances with DJ Calvin Harris and actor Tom Hiddleston, the latter of whom she dated just weeks after Harris broke things off. Still, Swift has since found love with the British actor Joe Alwyn. For her sake at least, let's hope this one finally works out.

2. Justin Beiber

Say what you will about the 23-year-old, there's no denying that this talented star has led a troubled life in recent years. He has everything a guy his age could ever want: Fame, talent, wealth, good looks. But to Justin, that probably means nothing without the love of Selena Gomez, his first and one true love.

Instagram/ Windsor Dalton

But having cheated on her numerous times, Gomez called things off with Justin and has since moved on with the hip-hop superstar, Abel Tesfaye, more commonly known by his stage name, The Weeknd. 

Since the relationship, Bieber has remained single, and despite dating a string of models, including Hailey Baldwin, he's never let the relationship last more than a few weeks, and that's likely because he still goes to bed every night wishing Gomez would take him back.

3. Britney Spears

Leave Britney alone was a phrase that entered the cultural lexicon the moment a YouTuber exclaimed those very words, and it's almost reflective of Britney's social life since finding fame. Sure, she's had immense success in the music industry, but she hasn't managed to replicate that success with men.

Shutterstock/ Joe Seer

In fact, after being dumped by Justin Timberlake after he discovered her infidelities, the Toxic hitmaker married childhood sweetheart Jason Alexander before it was annulled 55 hours later. Then came back up dancer Kevin Federline, whom she married in 2004 and had two children with. Despite this, Spears filed for divorce three years later. 

Her last major relationship was with her former talent agent, Jason Trawick, which started in 2009 and ended in 2013.

4. John Mayer

John Mayer is now 40-years-old, and despite touring the world, selling out stadiums, banking serious dough and still looking like an absolute stud, he is yet to find a woman to settle down with, despite a string of past loves.

Shutterstock/ Debby Wong

These include Taylor Swift, Katy Perry and Jennifer Aniston, the latter of whom he claims he has never truly gotten over. 

Today, Mayer rarely dates, and instead spends most of his free time alone in his sprawling and sequestered Montanna mansion.

5. Drake 

He's made millions as a hip-hop artist in touch with his emotions, with both men and women relating to a melancholy Drake never appears able to let go of.

Shutterstock/Twocoms

But then again, that's understandable. After all, he has been dumped twice by Rihanna, been friend zoned by Nicki Minaj and had many flings that have led nowhere, which just goes to prove that money can't buy love, even if groupies throw themselves at you. 

In the words of the man himself, "How you supposed to find the one when anyone will come with you.'

6. Katy Perry

Poor old Katy probably thought she discovered everlasting love early on in her career when she made the mistake of marrying the then-lothario, Russell Brand.

Shutterstock/ Everett Collection

Like most women, Perry was smitten with the actor and comedian, but the feeling wasn't mutual because not long after tieing the knot, Brand soon got bored and filed for divorce. After the divorce, Perry gave love another shot with the British actor Orlando Bloom, though it didn't last long and despite reports of a romance between Robert Pattinson, Perry remains single.

7. Sandra Bullock 

As we wrote earlier this week on OMG Lane, Sanda Bullock has had some pretty rotten luck with men over the years, and she hasn't helped herself by choosing to marry hotheads like Jessie James, who cheated on her more than once.

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Bullock's also had ill-fated courtships with the Hollywood stars Matthew McConaughey, Ryan Gosling and Tate Donovan, but has since had better luck with the photographer Bryan Randall, whom she has dated since 2015.

8. Tom Cruise

Yes, he's a Scientologist. And yes, he's a bit crazy, but boy oh boy is he a good actor. He's arguably the last of his kind, a true movie star who can carry a film, so Cruise has, unsurprisingly, had his fair share of women over the years, including the sexy Spanish actress Penelope Cruz, though his failed marriages to Mimi Rogers, Nicole Kidman, and Katie Holmes are his most noted.

Shutterstock/ Featureflash Photo Agency

Now 55, (not that he looks it), Cruise is rumored to be dating the British actress, Vanessa Kirby, though whether the Mission Impossible star wishes to tie the knot again is unlikely. 

9. Jude Law

Jude Law has fathered six children, two of which came from out-of-wedlock relationships with models. Law was also married to the actress Sadie Frost before they amicably divorced in 2003.

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Then came Sienna Miller. After a whirlwind relationship, Law proposed to her and the couple seemed destined to be one of Hollywood's hottest married couples until Law shot himself in the foot by cheating on her with his children's nanny.

Sometimes, being unlucky in love is because of your own actions, as Law has proven.

10. Jake Gyllenhaal

Whether it's playing a combat troop with a shaved head or a creepy psychopath with a man-bun, Jake has the envious gift of looking good every waking minute of the day which makes his inclusion on this list even more surprising!

Denis Makarenko/ Shutterstock

Indeed, aside from being the first celebrity to break Taylor Swift's heart (You should've been there, Jake), Jake hasn't had much to shout about in the romance department, although we're sure he's more than content with a stellar acting career and being one of the hottest bachelors in Hollywood. 


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