Britney Spears
Britney’s love life remains full of many ups and downs, and it all started in 2002 with her split from Justin Timberlake. She didn’t do herself any favors when she jumped into a quickie Vegas wedding to her childhood friend Jason Alexander, which was annulled a whopping 55 hours later. Her next marriage was probably the most well-known among the public, to Kevin Federline. That one lasted a whole two years! Sadly, the third time wasn’t the charm for Britney. She became engaged to Jason Trawick for just over a year when they split in 2016. So it looks like it’s back to the drawing board for the pop princess. Despite her bad luck, she says, “I still believe in love and that sort of thing.” I think it’s safe to say Britney isn’t ready to lay down in defeat just yet. Hit her “Baby One More Time!”
Jennifer Love Hewitt
She might have the word “love” in her name, but Jennifer Love Hewitt has had a bit of a rough time with it over the years. Though she has been married to actor Brian Hallisay since 2013 and has 2 children with him (fingers crossed this one sticks!), it wasn’t always smooth sailing before this point. She has called herself a “love-aholic,” and has dated such characters as Will Estes, Stephen Dorff, John Mayer, Carson Daly, John Cusack, and many others. Jennifer was engaged to Ross McCall for less than a year before she called it off. She dated singer John Mayer for a time, and is his muse for his hit song, “Your Body is a Wonderland.” Her little black book of the past is a long one. Let’s hope the 37-year-old actress has found her forever Prince Charming and is done with her bad luck!
Taylor Swift
Despite being only 27, Taylor is swiftly making her way to the top of the “Most Exes” list, many of which are Hollywood A-listers. She has dated somewhere around a dozen different famous stars, including Jake Gyllenhaal, John Mayer, Harry Styles, and Calvin Harris, with none of these flames lasting longer than a year. As we all know, her trademark is writing a hit song or two about the breakup in not-so-subtle lyrics, which is a fan’s best insight into what made her latest relationship crash and burn. T-Swift’s long list of boyfriends past might make her unlucky in love, but her bank account is just the opposite! Word on the street is that she’s back on the market…looks like she’s got another blank space–in her wallet!
Paris Hilton
This serial dater takes this list to a whole new party girl level. Paris Hilton has access to it all–riches, booze, the hottest party places, a new wardrobe every week. The one thing she can’t seem to get her hands on is her Prince Charming. He’s the one thing she can’t buy. On her list of exes lies Ryan Gosling, Criss Angel, John Mayer, Brody Jenner, Chad Michael Murray, Benji Madden, Nick Carter, Adam Levine, and a slew of others. This broad has probably dated half of Hollywood by now! Slow down, princess, we can’t keep up with all of your boy toys long enough to write about them!
Jennifer Lopez
J-Lo’s been playing the game of love for a while now, and she still hasn’t found Mr. Right. She first married Cuban waiter Ojani Noa, and that marriage ended with lawsuits and still-unsolved issues between them. After that, she dated Sean “Diddy” Combs, until he was arrested for possession of a weapon and stolen property, marking the end of that relationship for Jenny from the Block. She married her former backup dancer Cris Judd, and 10 months later found herself divorced and single again. J-Lo was sure she had found her prince in actor Ben Affleck, and the two became engaged, only to call off the wedding a day before the wedding date. She was married to Marc Anthony for seven years, but they divorced in 2014. Since her split with Marc, she added Casper Smart to her list of ex-boyfriends, and is now flirting up the 17-years-younger Drake. Talk about a tragic love life! This mama can’t seem to catch a break!
Tom Cruise
Tom Cruise has now been divorced three times. His first marriage with actress Mimi Rogers lasted three years before coming to an end in 1990. Rogers reportedly was the one who first introduced Tom to Scientology. After that one bit the dust, he was married to actress Nicole Kidman for 10 years before their divorce (which was said to have taken place because of his Scientology beliefs). Cruise dated Penelope Cruz for a bit before his widely-known marriage to Katie Holmes for five and a half years. After that infamous breakup (possibly also due to Scientology), Tom is still cruising for his Cinderella. It seems that the solution to most of his relationship problems could be making a certain life change…or maybe it’s just plain science!
Jennifer Aniston
For being in such high demand on Friends, Jennifer Aniston has sure had a rough time finding her forever man! Her first marriage to Brad Pitt ended 5 years later, after Pitt was allegedly having an affair with fellow actress Angelina Jolie. Since then, she has dated such characters as John Mayer, Vince Vaughn, and British model Paul Sculfor, all unsuccessfully. Hopefully she’s found her forever in the slightly-younger actor/director/screenwriter Justin Theroux, whom she married in 2015. The 48-year-old actress may have missed her window for having her own children, but you’re never too old to find the right person for you!
Eva Longoria
Eva Longoria’s first marriage to actor Tyler Christopher lasted only 2 years, but her second marriage is where the real scandal comes in. She married French basketball player Tony Parker in 2007, and three years later discovered that he was cheating on her with the wife of one of his teammates! She found hundreds of text messages between Parker and his mistress, and Eva filed for divorce soon thereafter. Eva then went on to unsuccessfully date Hayden Christensen, Eduardo Cruz, Mark Sanchez, and Ernesto Arguello. She married Jose Antonio Baston in 2016. Hopefully the soap star is done with marriage drama from now on!
Selena Gomez
Selena has proven that she has some difficulty making a solid decision when it comes to her men. She was off and on with Justin Bieber for a couple of years, before it came to an end in October of 2015. After that ended, Selena had a bit of fun with the dating scene, living it up with a handful of guys, including Samuel Krost and Niall Horan (One Direction). She then dated Zedd, a DJ who produced one of Selena’s biggest hit songs. She ended that relationship only to go back to Justin Bieber for a bit, but then flip-flopped once again and returned to Zedd, splitting from him a final time shortly after. At the moment, the pop princess remains single. She might want to consider staying single for a bit while she figures out what she wants.
Rihanna
Thus far, Rihanna’s luck with men has been anything but good. After the felony assault charges on ex-boyfriend and rapper Chris Brown in 2009, Rihanna stayed single for several months, laying low and focusing on her music career. She then dated Dodgers baseball player Matt Kemp and rapper Drake. Then in 2012, she confirmed that she and Chris Brown had rekindled their relationship and were back together, though the reunion didn’t last long. Shortly afterwards, she briefly dated rapper Travis Scott, but soon decided he wasn’t the right one either! It’s not that she doesn’t TRY–the problem seems to lie in the idea that this singer is picky about her men. Maybe she should change up the occupations a little?
Sandra Bullock
Sandy B. isn’t the luckiest when it comes to the men in her life. She was once engaged to actor Tate Donovan, but they call off the the engagement after they had been dating for three years. She dated football player Troy Aikman, as well as actors Matthew McConaughey, Ryan Gosling, Ryan Reynolds, Chris Evans, and Michael McDonald. In 2005 she married motorcycle builder Jesse James, but that marriage hit the rocks when it Sandra discovered that James had been having multiple affairs with other women. She divorced him in 2010. Since then, she has been in a relationship with photographer Bryan Randall. She might be Miss Congeniality, but maybe congenial isn’t what men are looking for these days.
Lindsay Lohan
Lindsay Lohan has all kinds of reputations, but I think we can all agree that a heavy party girl is one of them. So it should be no surprise that her list of male conquests is rather involved. The former childhood actress famously dated teen star Aaron Carter for about a year, which gained a lot of media attention for an alleged love triangle between LiLo, Carter, and Hilary Duff at the time. Lindsay dated actor Wilmer Valderrama, then the Hard Rock Cafe heir Harry Morton. From there she went on to date British TV personality Calum Best, snowboarder Riley Giles, and DJ Samantha Ronson. The last we’ve heard is that she’s engaged to Russian millionaire Egor Tarabasov. Thus far though, her entire career seems to have revolved around partying with celebrities, and less about finding love. But maybe it’s working for her!
Halle Berry
Halle has been through the ringer with her love life–she has married and divorced three husbands, and has had one mega-publicized split with partner Gabriel Aubry. Her first marriage was to David Justice, which lasted 4 years. Her second marriage was to singer Eric Benét, which lasted 5 years, and after which her ex-husband underwent treatment for sex addiction. Next up came a partnership with model Gabriel Aubry, with whom she had a daughter, and was soon neck-deep in official custody battles for the child. They separated 5 years after they began their relationship. Marriage number three was to Olivier Martinez, which gave Berry a son and two years of marriage before divorcing once again. At the moment, Halle is single once more, but reportedly hasn’t given up on love altogether just yet. Keep fighting, sister!
Charlie Sheen
Charlie’s story is probably the most unique one on this list! His engagement to Kelly Preston ended after she got shot in the arm by his gun (purely accidental, of course!). Charlie married his first wife, Donna Peele, and that same year he was named one of the clients of a Hollywood escort agency operated by Heidi Fleiss. In light of this discovery, Sheen and Peele soon divorced. Other romances of his ended with an attack by a fork and several different accusations of domestic violence. He’s been married three times, didn’t make it to the altar at least one other time, and didn’t disclose his HIV-positive status to a few of his sexual partners. Ladies, any takers?
Drew Barrymore
She may only be 41, but Drew Barrymore has already been divorced three times and broken off two engagements. Her first marriage was to a British bartender named Jeremy Thomas when she was 19. Hubby number two was comedian Tom Green–that marriage lasted a whole year. Her third marriage was sure to be different all around with Will Kopelman, until they divorced four years later, finalizing it in August of 2016. As of late, she has claimed that her main focus for now will be on being a mom. That doesn’t mean we can’t hope for her to find someone, though!
Mariah Carey
Pop diva Mariah Carey has a “Vision of Love,” but it’s certainly not what most people envision when they hear the word “love life.” She’s been divorced twice, and she’s had a recent nasty breakup with her billionaire fiancé James Packer. Supposedly her latest fling is with backup dancer Bryan Tanaka, but who knows? This woman hops from man to man so fast that it’s hard to keep up!
Johnny Depp
Dear ol’ Johnny knows his way around the ladies, it seems. Or maybe he doesn’t, depending on how you look at it. He’s been married and divorced twice, and unsuccessfully engaged to another two women. He dated actress Kate Moss for four years. His divorce from Amber Heard is one of the most drama-filled stories out there, with his ex-wife placing and retracting abuse allegations all over the place. Johnny Depp may have simply portrayed a pirate when he was Captain Jack Sparrow, but his love life is starting to look more and more like he’s adopted some of those personality traits in real life!
Cameron Diaz
The beautiful Cameron Diaz has been around the block a few times for sure! She has dated a long list of Hollywood A-listers, including Carlos de la Torre, Matt Dillon, Jared Leto, Justin Timberlake, and Alex Rodriguez. She married Benji Madden after being engaged for only 17 days, and she is still married to him today. Hopefully this marriage will stick–before Benji, she thought marriage was a “dying institution” that does not “suit our world any longer.” I guess she changed her mind on that front!
Ben Affleck
Although Ben’s list of exes isn’t especially long, the breakups have been exceptionally noteworthy. He started out with a three-year relationship with Gwyneth Paltrow, which at first ended nine months after they began dating, but then Gwyneth was able to persuade Affleck to co-star with her in Bounce. After they filmed, they once again resumed their relationship, but separated again not long afterwards. He dated Jennifer Lopez for eighteen months, and was even engaged to her, but the engagement was called off four days before the wedding, and they broke up soon afterwards. Ben and Jennifer Garner were husband and wife for 10 years before they announced their divorce. They have 3 children, and even though they are divorced, they still live together to keep the family together. That’s great for their kids, but how does that affect their love lives?
Kate Hudson
Kate Hudson’s garbage love life didn’t kick off until after her divorce from a 7-year marriage to Chris Robinson. She dated Muse singer Matt Bellamy, and was even engaged to him for around 3 years, during which they had a son. They ended their engagement without ever becoming married, however, and that’s when the real fun began. Kate’s discard pile grew to include Lance Armstrong, Owen Wilson, Justin Timberlake, Dax Shepard, Baron Davis, Shannon Leto, Heath Ledger, Adam Scott, and Alex Rodriguez. She certainly knows her way around Hollywood!
Katy Perry
Following her 14-month failed marriage to Russell Brand, Katy Perry was a mess of hot and cold. She’s been running back and forth to singer John Mayer for some time now. She says that John cheated on her, for which she left him once, then began this to-and-fro game of taking him back, then dumping him again, over and over. At one point she took a break from John and got involved with the DJ Diplo, but when that relationship didn’t work out, she went right back to John for another here-and-gone-again routine. Perhaps this is the inspiration for her song, “Hot n Cold?”
George Clooney
Even though this Hollywood hottie is currently settled down with second wife Amal Alamuddin, George Clooney had quite the dating record before finding her. It was almost as though after his marriage to Talia Balsam ended, the dating scene became his own form of therapy. His little black book included Kelly Preston, Krista Allen, Teri Hatcher, Lucy Liu, Elisabetta Canalis, Lisa Snowdon, and Renée Zellweger. We hope he found the one, now that his wild yesteryears have passed!
Alyssa Milano
Actress Alyssa Milano may be settled in (hopefully for the long haul) with hubby David Bugliari now, but she has quite the impressive collection of ex-boyfriends under her belt. Her list includes Mark Wahlberg, Justin Timberlake, Kirk Cameron, Fred Durst, Jason Jondon, Eric Dane, Corey Haim, Scott Wolf, Corey Feldman, Jonathan Silverman, David Arquette, Barry Zito, and Brad Penny, to name just a few. This girl had a wild hair back in her younger days, but we hope she found her Prince Charming in her current husband.
Kim Kardashian
Kim Kardashian will always be remembered for her famous 72-day marriage to NBA player Kris Humphries. She made sure that it was widely televised and publicized, and then filed for divorce soon thereafter. She began dating Kanye West while she was still married to Humphries. Even before her marriage to Kris, she had a three-year marriage to Damon Thomas. The strikes on her part in the marriage department seem to have a common theme of widespread media attention, which makes it difficult to have real conversations. Word on the street is that Kimye has been having some problems lately as well. Will it last, or are they in trouble?
John Mayer
Singer John Mayer has been at the top of notable serial dater lists for a long time. This heartbreaker has dated Jennifer Love Hewitt, Jennifer Aniston, Cameron Diaz, Jessica Simpson, Minka Kelly, Vanessa Carlton, Rhona Mitra, Taylor Swift, Milana Vayntrub, Scheana Marie, Katy Perry, and Reena Hammer. Notice anything about this list? John seems to be the one they all go to when they’re not sure what they want. Coincidence? Or maybe just charisma?
Ed Sheeran
The ginger singer Ed Sheeran might be young, but his love life is less than impressive–in fact, it’s rather disappointing indeed. He’s said that he was betrayed by two different ex-girlfriends, who cheated on him. Poor Ed! We still believe the right girl is out there for him. He just needs to give it a bit more time!
Leonardo DiCaprio
Leo is another of our serial daters who just can’t seem to settle down with the right lady love. He’s dated actresses and models galore, including Naomi Campbell, Gisele Bundchen, Bar Refaeli, Blake Lively, Trishelle Cannatella, Bridget Hall, Natasha Henstridge, Kristen Zang, Vanessa Trump, Demi Moore, Paris Hilton, Miranda Kerr, Rihanna, Toni Garrn, and several others. He is currently single, although judging by his record, it won’t be long before this loverboy sights his next target.
Kirsten Dunst
Although she seems to be an acquired taste for movie fans, Kirsten Dunst has supposedly made her way through a long list of celebrity hotties over the years. Her list includes Ryan Gosling, Jay Hernandez, Zach Braff, Adam Levine, Justin Long, Jake Gyllenhaal, and Garrett Hedlund, to name a few. At the moment she is engaged to her Fargo co-star, Jesse Plemons. Good luck, Dunst!
Jenny McCarthy
Playboy model Jenny McCarthy ended her first marriage to John Mallory Asher after six years of marriage back in 2005. She dated Jim Carrey for five full years, and then publicly Tweeted their split to make the announcement. Since then, she’s added Jason Toohey, Paul Krepelka, Brian Urlacher, and her second husband, Donnie Wahlberg to her named pile of accomplishments.
Justin Timberlake
Justin Timberlake might be all settled down with his beautiful boo Jessica Biel, but he wasn’t always the doting dad he is now. We all remember his first famous relationship with pop diva Britney Spears. Since then he’s added names like Lindsay Lohan, Beyonce, Fergie, Alicia Keys, Alyssa Milano, Jenna Dewan Tatum, Cameron Diaz, Scarlett Johansson, Rihanna, Olivia Wilde, Olivia Munn, and Kate Hudson to his list of conquests. He’s been there, done that when it comes to the Hollywood dating game. We’re just glad he’s still in the business at all!
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