15 Celebs Who Have Made Terrible Dating Decisions

Celebrities are as known for their dating lives as they are for any other work that made them famous, to begin with. It's simply interesting to the general public to watch beautiful people date each other...and then break up and date other people and/or get back together. Who could look away? There are of course the celebrities who seem to get into well adjusted and happy long-term relationships. But then there are the celebrities who seem to crash and burn in the dating sphere over and over again. Those ones tend to get more attention paid to their dating lives for various reasons. On some level we can all relate, since most of us have plenty of our own dating challenges. But for some reason it always seems even more dramatic and tumultuous when you throw in a bunch of fame and money. Here are 15 celebrities who have made some pretty terrible dating decisions. Try to learn from their mistakes instead of emulating them.

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15 Halle Berry

Daily Mail

Halle Berry was once in a very abusive relationship. The man punched her so hard in the ear one time that she ended up puncturing an ear drum and losing 80 percent of her hearing in the ear. Halle's marriage with Olivier Martinez lasted just two years, and she reportedly had a fight with Gabriel Aubry that got physical at one point. After the incident, both of them were treated for injuries. When Halle and Gabriel split, she was ordered to pay him $16,000 a month in child support. It's hard to imagine that Halle would end up with so many men where drama was the name of the game, but we all have our types. It seems that sometimes people have to replay their same relationship mistakes over and over again before they are finally ready to move on and accept that they deserve a different type of love in their life. Halle happened to have children with a couple of these people so she will be linked to them forever, but hopefully she finds the love that she deserves.

14 Britney Spears


Let's not forget that Britney Spears once married Kevin Federline. That's not even just a bad dating decision, that seems to be a bad marriage decision. Many people tried to warn Britney against marrying Kevin since she has had a history of moving quickly in her relationships, but she didn't seem to listen. Britney has since admitted that she married Kevin for the wrong reasons. She liked the idea of having the marriage but maybe didn't think long enough about who she was choosing to do it with. It was right after Britney's rocky split with Kevin that she started partying a lot and then ultimately had her famous head shaving breakdown moment before heading to rehab. Whatever happened there it seemed to be stressful enough that Britney was sent into a bit of a tailspin. While Britney was in rehab she had to leave their two young sons behind, but today she calls them her "masterpieces."

13 Rob Kardashian


Rob Kardashian might not have seen the drama coming when he started dating Blac Chyna, but perhaps he should have. That doesn't seem like it was the best idea ever. They did have an adorable kid together, but of course, that also links them for life pretty significantly. Some people suggest that Blac was just after the Kardashian name, especially since she was trying hard to get her name changed to Kardashian. Her request was actually denied even while she and Rob were still together. The timeline of Rob and Blac's relationship is actually a bit confusing, but it included moving quickly at the beginning of the relationship and then lots of drama at the end. There were cheating allegations, restraining orders, social media cleanses, social media revenge attempts, reconciliations, and more drama. They are reportedly split but coparenting their daughter Dream.

12 Sandra Bullock

Closer Weekly

Sandra Bullock was undoubtedly attracted to bad boy Jesse James. But then like many bad boys, he actually turned out to be a bad man who cheated on her. Their breakup ended up being pretty dramatic because Jesse was caught cheating on Sandra with not one, but many different women. Those things have a way of coming up eventually. Jesse probably felt pretty bad about it but he gave himself a healthy dose of credit for owning up after he got caught instead of denying the truth in the situation. “The relationship part I was able to put [aside]. I had to stand up in front of the media and take full account for what I did. And I took it all. I took 100 percent of it right on the chin. Nobody does that. Everybody denies it.” When they split Sandra kept the son that they had adopted together and Jesse has said that losing Louis was one of the hardest parts about the whole thing. Maybe he should have thought about his family before he started cheating.

11 Kim Kardashian

Radar Online

It's easy to forget that Kim Kardashian was first married at the age of 19. She eloped with Damon Thomas who was 29 at the time. The marriage obviously didn't work out, and it's supposedly because he was physically abusive and tried to pressure her into looking perfect. Luckily she got away from the relationship eventually, but that wasn't the end of her dating troubles. Kim also quickly regretted her marriage with Kris Humphries, but that seemed more like just a really failed match and less so because anything terrible was going on. Although it sounds like Kris made things complicated during the divorce process and she was actually still going through the divorce when she and Kanye got together. Side note, doesn't it seem a little weird to marry who guy who not only has the same name as your mom but also spells it the same way? That's a unique dating history that Kim has there. You could also say that dating Ray J wasn't the best idea based on the fact that Kim ended up with a tape leak, but others would say that's exactly what she wanted to happen.

10 Rihanna


Rihanna and Chris Brown seemed incredibly close and they undoubtedly had a real connection when they were together. But things ended after Chris punched her in the face so that makes it sound like a pretty bad relationship. Chris recently opened up about that relationship in a documentary and he did say that they were both physically abusive with each other. It just happened to be that one time that things went a little too far and ended up blowing up in his face. It's not to know without being there, but no one should be punching or getting punched for any reason. And then we have Drake who seems like the nicest guy in the world who's been in love with Rihanna for years. And yet she never seems to stick around with him long even though she dips in and out here and there. Perhaps she has a bit of the bad boy complex thing going thing. Time will tell whether Rihanna ends up setting on a good guy or not.

9 Sofia Vergara


Sofia Vergara has had quite an eventful life, and not always in the good ways. Sofia first got married at the age of 18 and had a child by the age of 20, but that relationship did not work out. Then her brother was murdered, then she had thyroid cancer, and then she dated Tom Cruise, then her boyfriend Nick Loeb was critically injured in a car accident. Apparently, when Nick and Sofia were together she had some of her fertilized eggs frozen in case they decided to have children at some point. Well after the two split up, Nick tried to sue her for the eggs saying that he had the right to have their children with or without her. Talk about chaos. Luckily Sofia seems to have moved beyond the craziness that her life held before, and today she is happily married to Joe Manganiello. The two tied the knot in 2015. She's also one of the highest paid women in TV, so looks like things turned around.

8 Jennifer Lopez


What's with all these incredibly gorgeous and talented women dating men who aren't good to them? Jennifer Lopez once dated the much younger Casper Smart who ended up cheating on her. It's hard to imagine that someone would do such a thing, but it just goes to show you that everyone has the same ups and downs in relationships no matter what. However Jennifer didn't seem to even skip a beat after the Casper drama, she just moved on and jumped right into the arms of now boyfriend Alex Rodriguez. Jennifer has also had failed romances with Ben Affleck, Puff Daddy, Marc Anthony, etc. She once famously said that "men come and go" which is not how some people look at relationships when they have very strong connections. But she seems to know what she's doing because she's never let anything in her life slow down her career path at all. Has Jennifer ever had a moment where she seemed to lose a step in line? Not really.

7 Drew Barrymore

Daily Mail

Drew Barrymore has certainly had her fair share of dating and marriage dramas. So Drew was famous from a young age and you could say that she got involved in the Hollywood stuff a bit too young for her own good. Some of the men that Drew has dated include Justin Long, Luke Wilson, Spike Jonze, Fabrizio Moretti, Eric Erlandson, Corey Feldman, Balthazar Getty, Leland Hayward III, David Arquette, Corin Nemec, Jamie Walters, Jeremy Thomas, Eric Erlandson, Edward Norton, Henry Thomas (who played her brother in E.T.), Tom Green, Sam Rockwell, Will Kopelman. She's also been married three different times and engaged even more. The first time that Drew got engaged was at the age of 16, which obviously did not work for probably a wide variety of reasons. Drew's most recent marriage didn't work either, but she has shared that she's thrilled to have the daughter's from it that she does.

6 Kelly Rowland


Former Destiny's Child member Kelly Rowland has opened up about the fact that she was once in an abusive relationship. Kelly has kept the identity of the man private and admitted that it happened when she was too young to know any better. “A piece of me would just go away every time he would say something. I’ll never forget those things. I’ll forgive him … he’s a different person now but it was things to tear me down as a person, as a woman. I was just so young and allowed him to do those things to me.” Kelly also sang about the relationship in her song “Dirty Laundry.” But luckily for Kelly, it seems like she has been able to move on from the situation and is clear about the fact that she does not want to be in abusive relationships anymore. Kelly said that her current husband knew that she was the one by their first date, while Kelly knew by the third date. When you know, you know. So they say.

5 Pamela Anderson

Us Magazine

Pamela Anderson has been known for having a bit of a rocky dating history. Pamela and rocker Tommy Lee have an on and off again relationship. They actually first got married after knowing each other for only a few days, and it was considered a tumultuous relationship. Pamela has had multiple relationships with Rick Salomon, one time which resulted in a marriage. (Rick also dated Paris Hilton and Shannen Doherty.) She also dated Criss Angel, David Spade, magician Hans Klok, football player David Binn, Ray J, Usher, Mark McGrath, Stephen Dorff, Fred Durst, Kid Rock, Michael Bolton, Arsenio Hall, Dean Cain, model Marcus Schenkenberg, Kelly Slater, Brett Michaels, Antonio Sabato Jr, Vince Neil, David Charvet,Scott Baio, and many other equally seemingly random other people. Obviously, most of those relationships did not last the test of time.

4 Kate Moss


Kate Moss was in a long-term on and off again relationship with Pete Doherty. They were reportedly in an abusive relationship and also did a lot of drugs together. Any way you try to look at that it couldn't have been a healthy relationship. After they broke up Pete compared their relationship to the Vietnam War. Sounds nice. Kate also dated Johnny Depp for a few years and after their breakup, she explained that their relationship involved "years and years of crying." Sounds like we have a pattern here. Later Kate Moss married Jamie Hince, but that too only lasted a few years. Jamie was allegedly citing "adultery" as the issue there and was not happy that Kate moved on to a new relationship as quickly as she did. As her marriage was dissolving she started dating Count Nikolai von Bismarck, who she is reportedly still with now. Hopefully, that relationship is a little less dramatic than the others.

3 Lindsay Lohan


Lindsay Lohan has had a variety of high profile relationships, a few of which haven't seem great. She dated DJ Samantha Ronson for a while but they were fighting publicly the entire time. Lindsay said that the relationship was toxic and Samantha said that she had panic attacks throughout it. Samantha's mom even called Lindsey "psychotic" after the women broke up.“Two toxic people cannot be together. End of story. We’re friends now. That’s how it started so I think that’s how it was meant to be.” One of Lindsay's more recent dramatic relationships was that with fiance Egor Tarabasov. They also had some public fights such as Lindsay throwing his phone into the ocean after finding a suspicious text and then posting to social media that he was "cheating on her with a certain type of woman" She also at one point had to call the police after claiming that Egor tried to strangle her. It's easy to assume at this point that Lindsay actually likes the drama.

2 Kourtney Kardashian

Kourtney Kardashian has had a very long on and off again relationship with Scott Disick. Some might say a little too long. The two are currently off but it seems like Kourtney spent many many years dealing with Scott's drama when she could have been moving on to a supportive and healthy relationship where she didn't have to mother the father of her children...in addition to their children. The two first met in 2007, so it's been quite a long time. Kourtney dealt with Scott's constant drinking and complicated issues for years. That is until he was snapped partying with and getting close to some other women when they were supposed to be together. Eventually, they broke up for good and now Kourtney is dating the much younger Younes Bendjima. Kourtney has reportedly not yet introduced her and Scott's children to Younes since she does not know whether the two are the real deal. Makes sense.

1 John Mayer


John Mayer makes the list for giving up Katy Perry. Overall John seems to have had a very normal (or great) list of girlfriends over the years. Jennifer Aniston, Minka Kelly, Jessica Simpson, Jennifer Love Hewitt, Taylor Swift, Rashida Jones, Cameron Diaz, Rhona Mitra, Vanessa Carlton. But it's Katy Perry where the head scratching comes in. John and Katy had an on and off thing for a while and then after they broke up and she moved on he talked about how much he missed her. He said that he wrote the song “Still Feel Like Your Man” about the relationship with Katy. When asked about it he said: “Who else would I be thinking about? And by the way, it’s a testament to the fact that I have not dated a lot of people in the last five, six years. That was my only relationship. So it’s like, give me this, people.” John has also said that they actually feels like settling down now. Time will tell if there's still a chance to work things out with Katy.

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