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15 Celebs Who Always Date People Under Their League

Looking for love as a normal person is hard. So, one has to imagine that looking for love as a high-profile celebrity is next to impossible. Not only are people afraid to ask celebrities out, they are also notoriously hard to get anywhere near (for good reason). This could be the reason why the celebrities on this list have fallen into the habit of picking crappy partners. They could probably just be a result of going after the people who are in their inner circle because it’s too hard to find love outside of that. Or, they could genuinely believe that the partner they choose to be in their life is their perfect match. Why wouldn’t they believe that? Everyone wants to believe that they are surrounded by good people. However, there are a number of celebrities out there that we need to take to task. For some reason, they continuously get screwed over in relationships. They always end up picking a partner that is just not for them. Fans and haters alike can see the breakup coming from a mile away and most of the time we want to grab them, shake them, and say, “open your eyes." Other times, we want to sympathize with them because they are doing what everyone else in this world is doing— looking for love. Being single can really suck it’s coupled with loneliness, boredom and sometimes being jealous of those who are coupled up. That being said, it’s still better than wasting years with someone who wasn’t right from the beginning.

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15 Mariah Carey And Her Backup Dancer, Bryan Tanaka

via Entertainment Tonight

Where do we even begin with Mariah Carey? She has struggled her entire career with finding a man and KEEPING him. Carey has picked crappy partner after crappy partner; it’s as if she is just picking the same person continuously and they just have different host bodies. Beginning with Tommy Mottola, she felt trapped and almost controlled. She didn’t get married again for a really long time, but she dated here and there. Then, she decided to get married again and she chose Nick Cannon, uh okay. Cannon was younger and for a while, many people believe that they would not work out, but they attempted to prove us all wrong by getting married and having kids. Now, she has moved on with her backup dancer, Bryan Tanaka, and to be honest, we don’t see a lot of hope here. He doesn’t seem to be on her level and their relationship comes off as very awkward and staged.

14 Jennifer Lopez And Alex Rodriguez

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Jennifer Lopez has always had very public relationships and none of them have worked out. It’s as though she chooses men based on what she wants her personality to be for that time. When she dated P. Diddy, she was bandana-wearing "Jenny From The Block," when she dated Ben Affleck, she was a glammed-up Hollywood queen, and when she married Mark Anthony, she was super into her Latina roots. It’s like come on, stop being so predictable and maybe you will be able to find someone who is genuine and a relationship that is lasting. She always seems to be going through a breakup. No one would suspect that someone like Jennifer Lopez would struggle with love but seriously, she always picks the guys that end up screwing her over or moving on to someone "better."

13 Mel Gibson And 27-year-old Rosalind Ross

via UPI.com

Mel Gibson is a complete mess, and this could be the reason why he constantly struggles to find a balance in life. Ever since his divorce from his wife, Robin, after 26 years of marriage, he has not made good decisions about women. He married Oksana Grigorieva and had one child with her before realizing that they were just not right for each other. They had a public, awkward, crazy, and horrible divorce that is still burnt into the minds of those who listened to the voicemails. Now, he is with Rosalind Ross who is 27 years-old (he is 62). They also have a child together, which makes a total of nine kids for him. In fact, his current partner is younger than some of his kids. For some reason, we don’t see this relationship lasting too long either.

12 Kim Kardashian And...Everyone

via The Daily Beast

Kim Kardashian may have finally met her match with her husband, Kanye West, but before him, she made the rounds with some real duds. Many people forget that Kim was married at 19 to a music producer. The relationship lasted four years and afterward, as her popularity grew, she dated Ray J, Reggie Bush, married Kris Humphries and had a few dates here and there with random celebrities like Nick Lachey. All of them ended in awkward heart-breaking ways like with cheating, the release of an adult film, and a supposed publicity stunt. Now that she has West and three beautiful kids, she seems to be settled and happy. Let’s be honest, the couple compliment one another, which is a rare find with celebrities. I guess it’s true what they say about having to kiss a lot of frogs...

11 Madonna Dated Tupac, Sean Penn, Guy Richie and etc...

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Madonna truly struggles with relationships and she always ends up being single. She has been married a few times and dated a whole lot of high-profile celebrities like Sean Penn, Tupac, and Guy Richie. For one reason or another, no one seems to stick around. This could very well be her own doing but it’s not like all the guys she has been with have been class acts. Take Penn for instance; apparently, they had an extremely toxic relationship and Tupac was literally a gang member first and a rapper second. Madonna even dips her foot in the lady pond every once in a while but she couldn’t even make that work. She had an ongoing hook up with Jenny Shimizu, have you seen this woman? She’s gorgeous. Then, there was her fling with Sandra Bernhard. It’s just weird that nothing seems to last with her.

10 Taylor Swift Is A Notorious Serial Dater

via Capital FM

Normally, we are calling out Taylor Swift for being a user but here's the deal, no matter how annoying she is, we have to admit that she has dated a few losers. Let’s start with John Mayer. He is the ultimate womanizer and he will admit it himself. If you take a look at his track record and some of the comments that other celebs have made after dating him, we are inclined to believe it’s true. She also dated Joe Jonas, who was rumored to have cheated on her. She and Jake Gyllenhaal also had an awkward relationship, where she accused him of never being around. And last but not least, her relationship with Calvin Harris, the guy who supposedly didn’t give her writing credits on a very famous Rihanna song. Need we say more?

9 Melanie “Mel B” Brown And Stephen Belafonte

via Hindustan Times

Mel B is going through a very rough divorce currently, but all her problems started years ago when she had a horrible custody battle with her first husband, Jimmy Gulzar. He trashed talked her and their relationship, saying that being with her made him want to kill himself (ouch). Another high-profile relationship was with Eddie Murphy but according to him, he doesn’t even know her and he denied the baby she had for years until he was forced into a paternity test. Surprise! He is the father if her second child. Fast forward to Stephen Belafonte, who she spent 10 years with and who is currently slandering her in the media and threatening to leak private tapes that they made together. She sure knows how to pick 'em.

8 Chris Brown And Rihanna And Everyone After Her

via nydailynews.com

We can safely say that the only somewhat sane relationship that Chris Brown had was with Rihanna. Ever since then, it has been a plethora of dancers, video girls, and social media models. When the relationships end, all of these women seem to have something crazy to reveal about Brown and his private life. In addition, he even fathered a child with one of them that he didn’t even know about until she was a toddler (or so he says). Brown is known for making some very questionable decisions but at some point, he is going to have to grow up. We know he is capable of being a grown man because of how we see him interact with his daughter. He really needs someone to vet these women before they have access to him.

7 Tori Spelling And Dean McDermott

via UPI.com

Tori Spelling only has one person that we can truly fault her for and that is Dean McDermott. However, what he has done is worth her being on this list. Spelling left her first husband and ended up with McDermott, who was actually married to another woman with a kid on the way. Of course, once a cheater always a cheater and he eventually cheated on Spelling so publicly and obnoxiously that she will never be able to live it down. Of course, when she was younger she had questionable partners as well like Brian Austin Green, but people expect that at a young age. To be a full-grown woman choosing to be with a married man, only to turn around and get cheated on, is embarrassing. Come on girl, do better. Some books should be judged by their covers.

6 Jennifer Aniston And Justin Theroux

via Metro

Jennifer Aniston has made this list for the simple fact that she always seems to pick partners that already have one foot out the door. She is a sought-after woman in Hollywood and let’s be honest, she could probably have any man that she wants but she ends up choosing the guys who always want more than she can give. Some of the biggest fails in her love life are her ex-husband, Brad Pitt, and soon to be ex-husband, Justin Theroux. She and Pitt had a very public break up and it made the world feel sorry for her but on top of that, a lot of news reports emerged that she was the cause of the breakup. Headlines accused her of not wanting kids and being more into her career than her husband. Now, these rumors are swirling again with her impending divorce from Theroux— she can’t catch a break.

5 Pamela Anderson And Tommy Lee

via Entertainment Tonight

Pamela Anderson has had her fair share or crappy partners and it’s as if she hasn’t learned from her mistakes at all. Her biggest mistake was Tommy Lee because she has two kids with him and will forever be bound to him. They recently made headlines because Lee pressed charges against his son for a physical altercation that the two got into. Anderson has had to defend her son's honor before with other men like when one of her kids got into a fight with now ex-husband, Rick Solomon (the same guy who co-starred in Paris Hilton’s adult tape). She married Solomon twice, believing him to be a changed man the second time around. She was also married to Kid Rock, who has his own questionable things going on. Her list of horrible relationships is endless.

4 Blac Chyna And 18-Year-Old YBN Almighty Jay

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Blac Chyna really needs to get a grip. Let’s start off by saying that she is no prize herself but the people she has chosen to date are also… let’s call them ridiculous. Besides the high-profile relationship with Rob Kardashian that ended horribly, she also had a high profile relationship with Tyga (we all know about his Kardashian connection). She continues to choose men essentially based off of how popular they are and how much money they have. This is why she will never find true love. Currently, she is dating an 18-year-old (she is 29) named YBN Almighty Jay and yes, he’s a rapper. Where she found time to find a new man amongst the lawsuit she has against the rapper, Mechie, for an adult tape released without her permission is beyond us.

3 Katy Perry And Russel Brand And Then All The Men After That

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Katy Perry is another one who just struggles with the men in her life. She was married to Russell Brand, who just couldn’t wait to divorce her. Since the divorce, he has said some crazy stuff about her in regards to their love life and her personality. Essentially, he accused her of being pretty dry in the bedroom and having a lackluster personality. She has dated John Mayer a few times as well. To us, it seems like he only dates her when he needs help with music. For instance, they were dating when they wrote the song "Who You Love." When that process was done, he dumped her. She also dated Travie McCoy for several years but that didn’t last because he has some personal demons to deal with. She also dated Johnny Lewis, the actor who killed his landlady and then fell to his death off the roof of her house.

2 Drake And Jennifer Lopez...Yeah That Happened

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Drake has professed his love for Rihanna time and time again, but she just can’t take him seriously and you know what, neither can we. Drake has dated so many people that shouldn’t even have access to him that we have to wonder what is going on up there in his head. He always seems to be connected to a club dancer (former or current) or a video vixen and when he does date high-profile women, it’s a date or two here and there and he’s right back in the club popping bottles with thirsty groupies. He has been linked to Nicki Minaj and Jennifer Lopez, who are both good candidates, but like we said, he always ends up back in the club with women like Jhonni Blaze, a dancer-turned-rapper.

1 Britney Spears And Kevin Federline And...Apparently Criss Angel?

via YouTube

We feel bad for Britney Spears because she has had an embarrassing few years in Hollywood and also always manages to find the worst partners. Starting with Kevin Federline, who she married and had two children with. He came out of the relationship looking like the good guy and living off of her hard-earned dollar. Then, during her downward spiral, she hooked up with Adnan Ghalib and Sam Lufti, who was a straight-up con artist. In her earlier days, she was linked to Fred Durst and Wade Robson, who both left their relationships with her with negative things to say. She just can’t catch a break. Currently, she is dating Sam Asghari, an aspiring actor, which just sounds like it’s going in a horrible direction.

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