30 Celebrities Who Are Notoriously Unlucky In Love

Celebs February 19, 2019 By Hugo

They have all the money in the world and millions of fans who adore them. Yet that special someone continues to elude them. For whatever reason, be it a hectic work schedule, an unfortunate series of dumpings, or simply an inability to find the right person to settle down with, these unlucky in love superstars are probably beginning to wonder if Cupid's arrow has evaded them altogether.

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So If you are upset at always being single on Valentine's Day don't be so hard on yourself because not only will you eventually find someone that loves you for you, you can also take comfort in knowing that some of the most beautiful stars in the world are facing the exact same problems as you are.

Here are 30 A-list celebrities who have garnered an unwanted reputation of being unlucky in love.


1. Jennifer Aniston

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Jennifer Aniston has certainly been unlucky in love in recent years. After finally moving on from being divorced from Brad Pitt after he found love with Angelina Jolie, she thought she'd found Mr. Right in the mould of the uber-stylish Justin Theroux. But that quickly ended in divorce as well. Despite such rotten luck, Jen didn't let her single-yet-again status stop her from throwing a massive 50th birthday bash at the Sunset Tower Hotel in Los Angeles this month.

Proving Jen is a lovely person who holds no bad blood, ex-husband Brad Pitt was in attendance, as well as Courteney Cox herself, whose ex-hubby David Arquette was also there. Only, unlike Brad, he turned up with his new wife. If you think that's quite overwhelming, get a load of this. Shortly after Pitt and Arquette rock up, up pops frickn' John Mayer. Oh, Jen!


2. Drake

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Poor old Drake! He may be the biggest male recording artist on the planet, but that still doesn't make him any less vulnerable when it comes to opening up his heart and having it tossed into the garbage! On two occasions, the R&B rapper was dumped by Rihanna and it seems this tortured soul just hasn't been able to move on.

Still, as all good artists do, Drake's turned his ongoing melancholy into a serious cash cow, and still holds the record for the most Spotify streams.


3. Katy Perry

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The Firework hitmaker will be the first to tell you that love hasn't treated her right. Since marrying the then-womanizing comedian Rusell Brand who shockingly requested a divorced via text, she proceeded to date another womanizer by the name of rock crooner John Mayer.

Proving she has a thing for emotionally unavailable men, she then got into a relationship with another infamous lothario by the name of Orlando Bloom. Katy, maybe the trick is to pick men that don't have such large numbers of female conquests... Just a thought. 


4. Eminem

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Adored by millions of music fans around the world, the iconic artist hasn't been able to replicate this enormous kind of success in his love life.

His on-off relationship with his ex-wife Kimberly Anne Scott failed to last, while his only other high-profile relationship ended in a slagging contest between himself and Mariah Carey.


5. Liam Neeson

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Liam Neeson experienced a kind of loss that you wouldn't wish on your worst enemy. He and his late wife Natasha Richardson were married for 15 years when Natasha suddenly died following a skiing accident in 2009.

Unsurprisingly, Neeson hasn't been in a serious relationship since that terrible day. 


6. Halle Berry

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Being one of the most beautiful women of our time doesn't hand you a free pass at love. Just ask Halle Berry. She has never really found long-lasting happiness with a guy and has been divorced three times.

Her first marriage was with the baseball player David Justice, followed by a second ill-fated union with singer Eric Benét. Proving that the third time isn't always a charm, Berry got divorced yet again with Olivier Martinez. But we're not finished. There was then a bizarre relationship with a Chicago dentist, who sued Berry for unpaid loans. Her hottest squeeze, the male model Gabriel Aubry, didn't end well either, with the Monster star having to go through a series of custody battles. 

All the money and fame in the world, but still no love. It just goes to show that fame and wealth is never the answer to happiness.


7. Sandra Bullock

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Sandra Bullock is another incredibly successful actress who hasn't managed to transfer her professional success to her personal life. She has had failed relationships with Ryan Gosling, Tate Donovan, Troy Aiken, and Matthew McConaughey to name but a few.

Things got even worse when she discovered that her ex-husband Jesse James was cheating on her. Thankfully, Bullock left him and is now in a relationship with a photographer called Bryan Randall. 


8. Tom Cruise

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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. These have included the sexy Spanish actress, Penelope Cruz, though his failed marriages to Mimi Rogers, Nicole Kidman, and Katie Holmes, all of whom left him, are his most noted.

A powerful force in the entertainment business and one of the most intense actors in Hollywood, Cruise, as lovely as he is, hasn't exactly done well in the world of love. Poor guy.


9. Taylor Swift

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Pop star Taylor Swift has had so many relationships, it's almost impossible to keep track of them all. And 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. 

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.


10. Britney Spears

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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.

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 the backup 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.


11. John Mayer

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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.

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.


12. Jude Law

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

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 over the years. 


13. Jake Gyllenhaal

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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!

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. 


14. Rihanna

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Rihanna's violent relationship with Chris Brown shocked Hollywood when the true details emerged from a domestic violence case. It almost (and really should have) sunk Brown's career. It left Rihana stunned by Brown's malevolent actions and understandably, her confidence was knocked.

Thankfully, the star eventually opened her heart again to fellow industry stars Drake, Leonardo DiCaprio and Travis Scott, but these were fleeting flings and little else. RiRi's first serious relationship since the Brown debacle was with the handsome Saudi prince Hasan Jameel. Things seemed to be going well but rumors of a breakup surfaced when they were pictured quarrelling at a swanky Mexican resort last summer.


15. Lea Michele

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Like Liam Neeson, Lea Michele experienced the loss of a romantic partner when her Glee co-star Cory Monteith passed away from a heroin overdose in 2013. The couple had been an item since 2011. Understandably, Michele was devastated and it took her well over a year before she decided to look for someone new.

Eventually, she had the heart to find love again with fellow thespian Matthew Paetz but the two split in February 2016. Fans of the star will now be hoping she fairs a little better with current boyfriend Zandy Reich, the president of the clothing company, Ayr.


16. Scott Eastwood

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Before his steamy breakout role in Nicholas Spark's movie adaptation of 'The Longest Ride', Scott Eastwood was more known for being the son of a rather famous actor. But nowadays, the American heartthrob is a star in his own right. But the humble and handsome star hasn't been that lucky with love- despite having the looks of a male model and fronting various fashion campaigns alongside A-list models like Gisele.

Yes, not even fame and good looks guarantee romantic love- something Eastwood knows all too well following the death of his last serious girlfriend Jewel Brangman following a car crash in 2014. Eastwood has since remained a bachelor, with his only public relationship appearing to be an on/off fling with the American supermodel, Charlotte McKinney. 

 For any eligible single ladies wishing to woo Eastwood into a relationship, the star revealed to People that he values three things in a relationship: Love, trust, and great sex.


17. Courtney Love

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Courtney Love (an ironic name for an unlucky in love person if ever there was one) is a true rock goddess, but her seemingly ecclesial status in the genre of rock n roll has been no guarantee of everlasting love. In fact, her first two relationships with bandmate Eric Erlandson and Smashing Pumpkins lead singer Billy Corgan were all ill-fated, and it proved no different the third time round- but for entirely different reasons.

When Love laid eyes on Kurt Cobain, it really seemed like she had found the love of her life. But as we all know, Cobain committed suicide in 1994, and Love has never managed to fully recover. She has had short-lived relationships with Edward Norton and the British comedian Steve Coogan, but nothing major compared to the love she had for the Nirvana frontman.


18. Tiger Woods

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Okay, this one is a bit different to the others in that Tiger Woods went out of his way to destroy his marriage by cheating on his wife and mother to his children with hundreds of prostitutes. This all became public when news of this morphed into a very public scandal in 2009.

His then-wife, the Swedish beauty Elin Nordegren, subsequently filed for divorce in 2010. His golf, as well as his love life, suffered tremendously and he is yet to win another major since the incident. As for his personal life, he finally dated 3 years later and found love again with the skier Lindsay Vonn. However, she dumped him in 2015. Woods will be hoping that his new girlfriend, Erica Herman, proves third time lucky. 


19. Mia Farrow

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Mia Farrow's first entry into the crazed world of marriage saw her marry a jazz crooner by the name of Frank Sinatra, who was 30 years her senior. Unsurprisingly, this marriage was short-lived and ended when she was only 22 years old.

Elven years later Farrow found herself in the same situation when she was divorced from Andre Previn. However, it was her relationship with director Woody Allen that is most publicized, not least because of how it ended. In a plot twist worthy of any Hollywood film, Farrow discovered Allen was sleeping with her adopted daughter Soon-Yi. Even worse? They are now together. 

We're not judging, but that's pretty strange.


20. Katie Couric

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One of America's foremost journalists was widowed in 1996 when her seven-year marriage to Jay Monahan tragically ended after he passed away from colon cancer.

Since the affliction, Couric has become a leading spokesperson for colon cancer awareness. After much soul-searching and rebuilding, she eventually moved on and remarried the financier John Molner in 2014.


21. Sheryl Crow

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The country superstar Sheryl Crow has never been short of admirers and has dated many famous people, including the guitarist Eric Clapton and the actor Owen Wilson.

However, Crow's 3-year relationship with the disgraced cyclist Lance Armstrong is probably the ill-fated courtship people remember most.


22. John Cusack

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John Cusack may be a ladies man, but after a string of failed high-profile relationships with the actresses Minnie Driver, Neve Campbell and Lili Taylor, the American actor, now keeps a low-profile.

Yes, it appears his 2011 relationship with Brooke Burns appears to have taken a lot out of him, with the star now 52 and still single and without any children.


23. 50 Cent

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50 Cent is a lothario if ever there was one. Ever since the success of his debut album 'Get Rich or Die Tryin' his ability with the ladies has never been in doubt. His more serious relationships, however, have failed to go the distance.

His flings include Vivica Fox, Chelsea Handler, Ciara, and perhaps more random than even Chelsea Handler, Lindsay Lohan. 


24. Johnny Depp

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Before Johnny Depp's much-publicised divorce from the actress Amanda Heard, Depp had a string of high-profile relationships, including a brief courtship with the British supermodel Kate Moss and the actress Winona Ryder.

It was after having his fun as one of Hollywood's hottest leading men that he settled down with the French actress and mother of his two children, Vanessa Paradis. But things never worked out, and you get a sense that Depp still harbours a deep-rooted longing for the mother of his children.


25. Harry Styles

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Harry Styles is by modern standards at least, a lothario. His relationships have been well-documented, and he is was even believed to be dating the supermodel Kendall Jenner having previously dated the pop star, Taylor Swift.

Still, at 25, Harry appears to have had no serious relationship since being dumped by Taylor Swift, and we sense, as the years go by, he'll be looking to settle down sooner rather than later.


26. Charlize Theron

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After splitting with Hollywood hardman Sean Penn, Charlize Theron once again found herself back on the Hollywood single's market. Though, with supermodel looks and pristine, gazelle-like legs,  it would be easy to forgive many men for feeling a tad intimidated when around someone of Theron's beauty.

Just look at her. It's unfair to be that beautiful, talented, wealthy and confident. But then again, maybe Theron would argue that it's unfair to have all these attributes and still be unlucky in love. Irony is a funny old beast.


27. Madonna 

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Madonna's career has taken her all over the world as well as putting her into contact and subsequent relationships with some of the most beautiful people in the world.

Examples included her marriages to the actor Sean Penn and the director Guy Ritchie and her relationships with Alex Rodriguez, Warren Beaty and Vanilla Ice. She's also known to love dating a male model or two. However, true love still evades the iconic hitmaker following her heated divorce from the British film director. 


28. Lindsay Lohan

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Known for her fiery attitude and sassy personality, Lindsay Lohan has had her fair share of celebrity flings over the years, with A-list names such as Colin Farrell, Justin Timberlake, Jared Leto, Orlando Bloom and James Franco all reportedly sharing a bed with the flame-haired beauty.

The former child star was also romantically involved with the female DJ, Samantha Ronson, but after years of failed relationships, drug abuse, partying to the extreme and even a stint in jail, Lohan appears to be someone who needs to learn to love herself before she can find love again with others.


29. Charlie Sheen

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Serial womaniser Charlie Sheen reckons he's slept with over 5000 women during a career which has seen him wreck three marriages and contract HIV.

Some notable names among those 5000 women he claims to have slept with include the actress Denise Richards, the porn stars Ginger Lynn and Heather Hunter and Kelly Preston, who he accidentally shot!


30. Keanu Reeves

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Keanu Reeves would be the first to tell you that fame and wealth are no antidote to a good life. In 1999, at the height of his popularity, Keanu Reeves' girlfriend, Jennifer Syme, delivered a stillborn girl named Ava.

Just eighteen months later, Syme died in a car crash. A tortured soul, Reeves also made headlines for that infamous photo of him eating alone on a park bench in New York. He didn't act for a few years after the personal troubles and has never been in a public relationship since Syme's death.


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