15 Hollywood Boyfriends That Are Giant Douchebags

If there are famous ladies out there, we urge you to stay away from these men!

If you think that you have been in a horrible romantic relationship, then just know that you are not alone. Even celebrities sometimes find themselves in a hot mess, and the results are not pretty. It never ceases to amaze us how many women (famous and not) will get with a man who is such an utter and complete jerk. The guys on this list are total losers and do not deserve to have a girlfriend - now or ever. While they range and vary in their levels of douchery, they all have in common the fact that they have completely disrespected women. Some men seem to think that girls exist solely for their entertainment and possession. Sound like anyone you know?

We encourage you to take a lesson from this list, whether you are a guy or a girl. It will teach you a thing or two about relationships and how love is about being unconditional, faithful, and of course, compromising for your mate. That doesn’t mean you don’t have a backbone, though. It is crucial that you hold your own and stand up for what you believe in. If the guys on this list ever met someone who was a total pushover, can you just imagine what the end results would be? We shudder to even think about it! Before we go off on a tangent about crappy men, let’s just get started with our list here. These 15 men will blow you away with how awful they are.

15 Amar’e Stoudemire

Via The305

This guy. He was dating hip-hop singer Ciara for a time, and this was after he had knocked up some girl named Alex Welch. Ciara just seems to have a really bad time with men, and the pattern continued with her relationship to Amar’e. After finding out that he had cheated on her, Ciara broke ties with Amar’e, and then later found out that he had gotten back together with Alex - the girl he had previously gotten pregnant. To make the wound fester even more for poor Ciara, Amar’e took to his social media account and proclaimed his love for Alex right there. He also uploaded a snap of himself proposing to Alex atop the Eiffel Tower in Paris, France. Then he made some long rant about how he loved her so much...which doesn’t even make sense, considering that he is a lying cheat! Ciara is definitely better off without him.

14 Eddie Cibrian

Via Celebuzz

Before he was galavanting around with singer LeAnn Rimes, Eddie Cibrian was dating Brandi Glanville, also known as the loudest and most dramatic cast member of The Real Housewives of Beverly Hills. In fact, Eddie and Brandi got so close at one point, that they decided to tie the knot in 2001. The couple had two children together, Mason and Jake. However, around 2009, it Brandi found out about Eddie’s cohorts with LeAnn, and that’s when all hell broke loose. Eddie ditched Brandi for LeAnn, and a divorce between Eddie and Brandi was finalized in the fall of 2010. Even once he got with LeAnn (they married in the spring of 2011), he was still a big douchebag to both women. He let LeAnn take care of Mason and Jake, while Eddie had little to no communication with Brandi about anything. Most of the time he is barely present at home with LeAnn.

13 Bow Wow

ViaThe Gazette Review

Lil’ Bow Wow is not so lil’ anymore, and he has gotten himself into big trouble with the ladies. The 29-year-old rapper’s personal life is so skewed and severed that we don’t think any girl would want to get with him. And yet, he does have a dating history that would make you cringe. Some of his more high-profile romantic escapades included dating Keyshia Cole, Erica Mena, and Joie Chavis, whom he got pregnant. In fact, Bow Wow may have been dating all three of these ladies at the same time...who knows? What we do know is that his ex-girlfriend, Erica Mena, has stated that Joie tore her relationship with the rapper apart, all thanks to her jealousy. Then Erica turned the tables and got angry at Bow Wow for posting an Instagram snap of himself getting cuddly with singer Keyshia Cole. This guy just can’t keep himself out of the drama.

12 Ben Affleck

We all know the story of Ben Affleck, and no list of douchebag Hollywood boyfriends would be complete with this guy. He dated actress Gwyneth Paltrow back in the day, but his demeanor was bringing her down, and she is quoted as saying that he wasn’t ready for a girlfriend at that point in his life. Basically, he just makes things complicated! Ask Jennifer Lopez, who was engaged to Ben and had to deal with him calling off the wedding four days before the ceremony was set to take place! Major douche move right there. Finally, we can all still feel Jennifer Garner’s wounds when she found out that Ben had been cheating on her with their children’s nanny. That is just about as low as you can go, and now Ben has a spotty relationship history that would ward off anyone. We guess some dudes are just meant to be single.

11 Kevin Federline


When Kevin Federline reminisces about his romantic relationship with Britney Spears, he calls it “crazy.” That sounds about right! K-Fed was working as one of Brit’s backup dancers when the two began to date. They were both young at the time; just in their early twenties, but still. Kevin was not the coolest boyfriend ever to Britney. He was feeding off of her fame and fortune, and the couple got a crappy reality TV series that is embarrassing to watch. Eventually, Britney woke up to the madness and realized that Kevin was a bad dad, totally absent-minded, and was only seeking to mooch off of her world-renown success. She dumped him and then Kevin adopted a “woe is me” attitude. Pitiful. This guy is better off on his own because we don’t want him ruining another woman’s life. The good news in the story is that Britney has rebounded and is doing well for herself.

10 Columbus Short

Via Pictures Of Celebrities

No one had really heard of Columbus Short until it was too late and his reputation was scarred for life. He was dating Karrine Steffans, and the two actually got serious with each other. Yet even marriage was not enough to make Columbus a faithful man. He was caught red-handed with another woman by Karrine herself! Really though, she should have known better. This is the man who had been arrested twice and was slammed with charges of domestic abuse. His ex-wife, Tanee McCall stated that he had threatened to kill her. He is not a dude you would want to go and marry. Anyway, Karrine got her revenge when she posted a video of Columbus in the act of his extramarital affair and she aired it on social media. This was just months after their marriage! She even tagged the post with all of the women that she suspected Columbus of cheating with.

9 Future

ViaCelebrity - Yahoo

Another one of Ciara’s ex-boyfriends was the rapper Future. Yet there is no future for this guy and Ciara. Even though the two were engaged to be married, things quickly took a turn for the worst, when Ciara found out about Future’s cheating and lying ways. The engagement was called off and Ciara moved on from him. However, once she began dating Russell Wilson, it seemed that her ex had some things to say. You see, Ciara and Future had a son (Future Jr.) together, and the senior Future was giving Ciara a hard time for allowing their son to be around Russell. It was some baby mama drama, all right, and it appeared that Future was criticizing Ciara and essentially telling her how to live her life. No way is that okay! If Future feels bad about losing Ciara, that is his own fault, not hers. Think before you cheat!

8 John Mayer

Congrats, John Mayer. You have been named the worst boyfriend in the world. Back in 2010, John had an interview with Playboy magazine, and the result was a public decree that he was the suckiest ex ever. The way he talked about his previous girlfriends was despicable, and he seemed to lack remorse for those failed relationships. He is known for referring to his ex-girlfriends as “choices,” and he constantly has horrible things to say about them behind their backs. He will bash them for their looks, their sexual activities, their hobbies...anything. He manipulates women and then tears them apart, calling them names and likening them to immature middle-school boys. By the way, that’s just creepy. Katy Perry, Taylor Swift, Jessica Simpson, Jennifer Aniston...they are all women who have been affected by a romantic relationship with John Mayer. It turns out his music and sappy lyrics are totally misleading!

7 Justin Bieber

Well, is this really a surprise? When Selena Gomez split from the Biebs, we couldn’t have been happier. She deserves someone so much better than that guy. Justin has a tendency to play the victim when it suits his own selfish needs. While he can hang out with his boxer friends like Floyd Mayweather (who is also on this list), Justin can also put on those sad puppy dog eyes and pretend that he is the one who got hurt, not the other way around. When he breaks up with a girl, he will stalk her social media and try to make amends, all in the name of (supposed) love. It’s quite disgusting, really. To be fair, he is trying to repair his public image. Whether that is genuine or just for more gain, time will hopefully tell. Is song “Sorry” an actual apology, or is it just a way for him to snag millions of more dollars?

6 Tiger Woods

Via Atlanta Black Star

Clearly Tiger Woods is on this list. Everything about this guy has crumbled. His professional golfing career is totally drained, and the guy has destroyed the lives of enough women to last two lifetimes. The stories of his extramarital affairs began to pile up, starting in the fall of 2009. Rachel Uchitel was the first woman to step forward about how she and Tiger were engaged in an affair. Shortly after that, more and more women began talking about their relations with Tiger. This guy was married and had two beautiful children with Elin Nordegren. The flack he received for his connections to multiple mistresses was totally valid, and Tiger ended up publicly apologizing and admitting that he had a problem (we believe he called it a sex addiction), and then he checked himself into rehab for 45 days. This guy used to be a role model to both children and adults. It’s a crying shame.

5 Scott Disick

Yes, we need to have a guy on this list who is connected to the Kardashian family in some way. The winner (or loser?) in this case is Scott Disick. Most people who watch TV know that Scott was with Kourtney Kardashian for quite some time; they even got married and had kids and everything. This man who likes his alcohol more than his lady would often talk down to Kourtney, leave her all alone with family responsibilities, and just act in a rude manner towards her most of the time. Besides that, he is highly suspected of being with Kourtney only because she is famous and linked to the ever-popular Kim Kardashian. If you’ve ever seen their show(s), Scott gets to rub elbows with the rich and famous and basically mooch off of Kourtney. Sure, he gave her beautiful kids, but he never really took care of them!

4 Chris Brown

There are plenty of names you can think of for Chris Brown, we just know it. Chris was famously pulled into the negative spotlight over his romantic relationship with singer Rihanna, who suffered from Chris’ violent and tumultuous ways. He was the poster child for domestic abuse and violence; someone from the Hollywood elite who was thrown into the public sphere for his lashing out and hurtful ways. Even after all of that negative press and attention, Chris ended up violating his probation, which got him into even more trouble. Somehow, he managed to get another girlfriend, but old, dirty habits die hard. Let’s just say that Rihanna was not the only girlfriend of Chris’ who was feeling the hurt. Moreover, Chris is obviously one of those males who sees women solely as objects to be possessed. He was in hot water for posting and sharing a picture of his ex-girlfriend’s bare butt on Instagram.

3 Sean Penn

He has been called pretty much every name in the book, and now Sean Penn finds himself on another list of terrible celebrity boyfriends. Sean may not be as active in Hollywood as he once was, but he is still gaining notoriety with his awful shenanigans (and that is putting it lightly!). Think back to when Sean was with superstar performer Madonna. There are various accounts of how abusive and violent he was with her. She even had to go to the emergency room after Sean reportedly hit her over the head with a baseball bat. Not only is Sean mean to the women he supposedly loves, but he is totally abusive to other people as well. Take for instance the time when he served two months behind bars for punching a fan of his in the face. A fan! We really don’t know what Charlize Theron was thinking when she decided to get wrapped up with him.

2 Wilmer Valderrama

Don’t know the name Wilmer Valderrama? Good, you don’t want to. Wilmer is one of the biggest douchebags in celebrity history, and Demi Lovato knows that firsthand. First of all, her romance with Wilmer is so on-again, off-again, that it is difficult to keep track of it all. Secondly, we all know that Demi has dealt with some pretty intense inner demons (mental health, substance abuse), and she was so brave and inspiring in publicly facing those problems head-on. Yet when she was staying away from drugs and alcohol and trying to keep herself on the straight and narrow, her boyfriend Wilmer ditched her to go party with some other girls who were okay with booze and drugs. He even took photos of himself posing with the waitresses at a sports club, all dressed in tight-fitting, skin-baring outfits. What a complete jerk. It looks as though he is the one who needs to get his act together.

1 Floyd Mayweather

Professional boxer Floyd Mayweather ended up bashing his ex-fiancee in public and yelling at her for miscarrying their baby. What kind of guy does something like that? Mayweather put his entire romantic relationship on full blast for the whole world to see, with zero regard for how his ex, Shantel Jackson, would feel about it. Oh, and Mayweather was canoodling with his massage therapist, Doralie Medina while he was arguing with his then-fiancee. And then he gets mad at her for seeing other people?! Clearly Mayweather has a whole lot of issues in the relationships department. He has no idea how to care for a lady, nor how to just be a decent human being. He blows all of his money, gets drunk and violent, and takes all of his insecurities out on whoever he is dating at the time. He may be the biggest douche of all.

Sources: Huffington Post, Daily Mail, US Magazine, Jezebel

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15 Hollywood Boyfriends That Are Giant Douchebags