Celebs Who Are Always Getting Dumped

Who wouldn't want to date a celebrity? They're rich, usually pretty attractive, and have cool, famous friends to mingle with. And yet, despite the apparent advantages, some of Hollywood's hottest just can't manage to keep a significant other around. Of course, there are others who play the field by choice, like Leonardo DiCaprio, who seems to date a new model every two years as if he's leasing women from a Victoria's Secret catalog.

In this case, we're talking about the hopeless romantics who don't have trouble finding love, but can't hang onto it once they find it. Some have come a long way from there — for example, previous serial monogamists and fairy tale enthusiasts Taylor Swift, Jessica Simpson, and Jennifer Love Hewitt are all happily settled down, as of this writing. However, some stars just can't seem to get their love lives together, even when everything else in their life is going swimmingly. Here are the celebs who are always on the receiving end of the Dear John letter (or, in some cases, the divorce filings and business blacklists).

It's almost inconceivable to think Halle Berry would have relationship trouble, but it's true — the stunner hasn't had a marriage last more than five years. Her first husband, baseball pro David Justice, told People that Berry always thought he was cheating during their four-year marriage; she said their 1997 split devastated her so much that she contemplated suicide. Next came singer Eric Benet, to whom she was married from 2001 to 2005, when he admitted to cheating on her and sought help for sex addiction. The Daily Mail reported that Berry was "severely depressed" when Benet moved out of their home.

Berry rebounded from Benet with model Gabriel Aubry. Though the genetically-blessed pair never married, they welcomed daughter Nahla two years into their romance, but they split in 2010. Berry then began dating actor Olivier Martinez in 2011, who got into a nasty physical altercation with Aubry on Thanksgiving in 2012. Despite the drama, Berry and Martinez married in 2013, and welcomed a son, Maceo. Berry and Martinez each filed for divorce from in October 2015 after Martinez hit a paparazzo with their son's car seat, TMZ reported.

In 2017, Berry confirmed she was dating Alex Da Kid. The romance was short lived, however: Us Weekly reported that just months into their relationship, the couple had split, and the music producer was spotted out and about with a mystery woman who most certainly wasn't the Oscar-winning beauty.

Tom Cruise was basically the king of Hollywood for a long time, but after his divorce from Nicole Kidman, his love life has been less than ideal. He rebounded with Penelope Cruz, his Vanilla Sky (2001) co-star, but they split after three years together, with Radar Online reporting that Cruise was heartbroken when Cruz dumped him over his involvement with the Church of Scientology. He also attempted to woo Sofia Vergara, Andrew Morton claimed in his unauthorized biography of the actor, but she was "fundamentally terrified" of Scientology.

Cruise then moved on with Katie Holmes, who made him happy enough to jump on Oprah Winfrey's couch. The pair tied the knot in November 2006 and share daughter Suri Cruise. Their marriage was reportedly a bizarre one, and it was speculated that the Church of Scientology was controlling Holmes in public. 

In 2012, Holmes filed for divorce from Cruise, using a Mission: Impossible-like system of burner phones, secret meetings with attorneys, and an iron-clad prenup that her dad drafted before they married. Since his split from Holmes, Cruise hasn't been in any serious relationships — at least none that the world knows about.

After Madonna and Sean Penn divorced, but before she dated a revolving catalog of her young backup dancers, the Material Girl got dumped a lot, often by rappers, who perhaps predicted her ill-advised grill phase. Vanilla Ice dated Madge in 1990, but says he dumped her upon release of her flop Sex book, griping (via The Huffington Post), "I broke up with her after she printed that book because I was hurt to be an unwitting part of this slutty package. It was disgusting and cheap. We were in a relationship yet it looked like she was screwing all these other people." Next came nightclub bouncer Jim Albright, who appeared to have eluded Madonna during much of their brief relationship before selling recordings and mementos of their romance years later.

Tupac Shakur also dumped Madonna, writing to her in letter obtained by TMZ, "For you to be seen with a black man wouldn't in any way jeopardize your career, if anything it would make you seem that much more open and exciting. But for me at least in my previous perception I felt due to my 'image' I would be letting down half of the people who made me what I thought I was."

Next came Dennis Rodman, with whom Madge was reportedly so obsessed, she went to acrobatic lengths to conceive a baby with him. (It didn't work. The world breathes a collective sigh of relief.)

Following her divorce from Bruce Willis, Demi Moore hasn't had a ton of luck in love. She married Ashton Kutcher in 2005 and they separated in November 2011, with reports abound that Kutcher cheated on Moore on their sixth anniversary that September (reportedly with poor Scott Eastwood's then-girlfriend, Sara Leal). They finalized their divorce in 2013. 

Since then, Moore's had short-lived romances with restaurateur Harry Morton and musician Sean Friday. Her most highly publicized relationship with was art dealer and inexplicable celebrity-serial-dater Vito Schnabel. Schnabel dated Moore for just a few weeks in late 2012 before dumping her, with a source telling Page Six that Schnabel "hated having photographers following him around." 

As of this writing, however, things may be looking up in Moore's love life. In November 2018, Radar Online reported that Moore was dating stylist Masha Mandzuka and that the relationship was so serious that they were raising Mandzuka's daughter together. Moore hasn't commented on the reported romance.

Comedian Pete Davidson hasn't even been famous for that long, but his love life has made so many headlines that he might as well be Warren Beatty. Davidson's first publicized romance was with fellow comedian and Girl Code personality Carly Aquilino, who he dated in 2015. He then took up with Larry David's daughter, Cazzie, who he dated off and on for two years before abruptly splitting from her and engaging in a whirlwind romance and quickie engagement to Ariana Grande. However, after Grande's ex Mac Miller tragically died of a drug overdose, she and Davidson called it quits. While it was initially unclear who did the dumping, in Grande's music video for "Thank U, Next," she makes it clear that it was she who pulled the plug, writing on his page of her slam book "Sorry I dipped."

Don't cry too much for Davidson. The Saturday Night Live star rebounded from Grande with actress Kate Beckinsale. The couple packed on the PDA to an almost repulsive extent before splitting after just four months. While it's not entirely clear who dumped whom, considering how touchy Davidson is about hearing her or Grande's names, it may be safe to assume he was left with a broken heart.

It's not easy being the biggest pop star in the world. In the documentary Lady Gaga: Five Foot Two (2017), the singer revealed that all of her professional success up to that point had come at the sacrifice of her love life. "My love life has just imploded. I sold 10 million [records] and lost Matt. I sold 30 million and lost Luc. I did a movie and lose Taylor," she lamented (via People). "It's like a turnover. This is the third time I've had my heart broken like this." Gaga was apparently referring to exes Matthew Michael Williams, ex-boyfriend Luc Carl, and ex-fiance Taylor Kinney. 

Carl, who was accused of being toxic in his "Bad Romance" with the chanteuse, admitted in a 2012 interview with Blackbook (via PopCrush) that Gaga's high-falutin' lifestyle didn't match up with his own dive-bar dreams. Kinney, meanwhile, possibly wasn't as invested in the relationship as the "Applause" singer was. Speaking in general terms on CBS Sunday Morning in November 2016 (which was around the time of her split from Kinney), Gaga said, "I think women love very hard ... and sometimes, I don't know that that love is met with the type of dignity that we wish it would be met with." She continued, "You know, we're not trying to make you less of a man. We just want you to love us as deeply and as wholesomely and as fully as we love you." 

Singer Liam Payne's first public heartbreak was when he split from Sophia Smith, his girlfriend of two years, who called time on the romance in October 2015. A source told Hollywood Life that Payne wanted to get serious with Smith, who wasn't ready. After splitting from Smith, Payne moved on with X Factor judge and singer Cheryl, who is 10 years his senior. The pair began dating just months after Payne and Smith broke up. They stayed together for over two years and had a son, Bear, before spliting in summer 2018. Cheryl hinted that Payne had a hard time balancing work and play.

In early 2019, Payne was linked to supermodel Naomi Campbell, who's 23 years his senior. After about three months, a source told The Sun that Payne was much more needy and into Campbell than she was into him, explaining, "She's just not into Liam any more and has cast him aside. Quite simply she got a bit bored."

Payne is the first to admit that he's unlucky in love. In October 2018, he confessed to BBC Radio 1 (via The Sun), "I once sang to a girl at the lockers. I asked her out a record number of times ... She went out with me because I sang to her and then dumped me the next day! The story of my bloody life, if I'm honest. It happens to me loads."

Rob Kardashian may have the worst luck in love out of his entire famous family. His first highly publicized breakup was from former Cheetah Girl turned The Real host, Adrienne Bailon. Bailon dated Kardashian from 2007 to 2009 and even got his name tattooed on her rear end before they split, reportedly because he cheated on her. She told Latina magazine (via the Daily Mail) in 2014 that she had no regrets about dumping him. "In my situation, it wasn't like, 'Oh my God! I made a mistake!' He strategically planned things out so that he could cheat on me, and that to me was so disloyal."

Karma may have come back for Kardashian in a big way in the form of singer Rita Ora. In 2012, Kardashian tweeted (via the Daily Mail) that Ora cheated on him with "20 dudes," adding, "How can a woman who is so busy trying to start her own career have time to be with so many dudes while in a relationship?!" Ora, however, told an Aussie magazine (via The Mirror) that she dumped him, adding, "I never thought it was actually a relationship, in all honesty."

And then there was Blac Chyna. The pair started dating in March 2016 after Kardashian's half-sister, Kylie Jenner, hooked up with Chyna's ex, Tyga. After a slew of mutual cheating and abuse allegations on both sides, Chyna walked out on Kardashian in December 2016, shortly after welcoming daughter Dream.

Rita Ora has had equal time on both sides of heartbreak. She famously caused Rob Kardashian's first social media meltdown after ending the relationship with him that she wasn't even sure she was in. Then, she dumped her collaborator and boyfriend-of-one-year Calvin Harris after he helped her pen almost entire album together, which included her hit "I Will Never Let You Down." Afterward, Harris reportedly prohibited Ora from performing "I Will Never Let You Down" at the 2014 Teen Choice Awards, saying in a bitter tweet (via Us Weekly): "You'll only know 1 side of the story RE Teen choice awards...But just know I had a damn good reason."

On the flip side of the relationship coin, in 2015 Ora began dating Blink-182 drummer Travis Barker. Barker was initially so enamored with her that he basically shouted it from the rooftops (and in the press). It didn't last long, however, with Barker allegedly telling The Mirror (via The Daily Mail) that he ended his three-week fling with Ora because he didn't want to be in a serious relationship.

Since then, Ora's had a series of relatively lower-profile romances, like her brief, public affair with The Amazing Spider-Man (2012) star Andrew Garfield. The Sun reported that Garfield called time on their four-month relationship in March 2019, with sources saying she was "cut up" over the split. Garfield reportedly dumped her because he wanted to keep things more private.

Jennifer Aniston is the tabloid mascot for heartbreak, starting with the end of her marriage to Brad Pitt. The couple married in 2000 and divorced in 2005 as he got closer with Mr. And Mrs. Smith co-star Angelina Jolie. Aniston admitted to Vanity Fair at the time that yes, she had been "lonely" and "upset" and had a small "pity party," but was moving on with the help of a therapist. She rebounded with Vince Vaughn, who she dated for a year — and who reportedly hated the attention that came with dating the A-lister.

After Vaughn, Aniston dated John Mayer from 2008 to 2009. Mayer dumped her because he wasn't ready to get serious, telling Rolling Stone in 2010 that even though he ended the relationship, he's "never really gotten over it. It was one of the worst times of my life."

Aniston and Justin Theroux dated next, eventually tying the knot in 2015. They announced their split in February 2018, though it's unclear who pulled the plug. Still, Aniston takes it in stride. As she told Vogue in 2008, "This whole 'Poor lonely Jen' thing, this idea that I'm so unlucky in love? I actually feel I've been unbelievably lucky in love. Just because at this stage my life doesn't have the traditional framework to it — the husband and the two kids and the house in Connecticut — it's mine. It's my experience. And if you don't like the way it looks, then stop looking at it!"