Gabi Conti
October 06, 2014 3:36 pm

Why are bad boys so irresistible? Is it because they stand out? Or is it how they don’t follow the rules? Or maybe it’s simply the motorcycle?

Or perhaps it’s the thrill you get when they finally do treat you well. Or how your heart melts when they finally show their sensitive side. So you endure them ignoring you and treating you terribly, because you remember that one time when they held you close and told you they loved you.

To quote the great Gloria Estefan & The Miami Sound Machine, “Bad, bad, bad, bad, boys, you make me feel so good.”

As someone who has dated my fair share of bad boys, I can tell you, it does not get better. Not usually, anyway. Yes, they look great in leather, and sure, though the smell of their cigarettes makes you cough, there’s something romantic about watching them take a drag, staring aimlessly off into the world.

So to make it easier for you. . . here are some bad-boy types you should not date based on these fictional characters.

1. Holden Caulfield from The Catcher In The Rye: The Loner

Perhaps most teenage girls’ favorite book is The Catcher In The Rye, not just because J.D. Salinger is a phenomenal writer, but because of what a hunk Holden sounds like. He’s tall. He wears a hunting hat when he’s not hunting (so. . .he’s fashion forward), he’s intelligent, and he romanticizes over little things like where the ducks go in the wintertime. Sign. Me. Up.

But he’s also angry. So very angry. He also doesn’t seem to like people much, so good luck trying to get him to like your friends. And something else he romanticizes? Innocence. Homeboy does not want to grow up. You want a man, and the Holden/loner type is definitely a boy.

2. Chuck Bass from Gossip Girl: The Womanizer

Is it a red flag that your type is Chuck Bass? Very likely. But how can you resist his aura, his black cars and his suits for every occasion. He’s basically a mini Mr. Big/Don Draper. While towards the end of the classic CW series, Chuck ends up cleaning up his act to woo Blaire, throughout the show, he was a bad boy and bad news.

And why you don’t want to date him? Aside from him sleeping with almost all of Manhattan? Hate to ruin Gossip Girl’s happy ending, but something tells me if he broke Blaire’s heart once, he’ll do it again.

3. Jordan Belfort from Wolf of Wall Street: The Party Animal

I’m noticing now that most of my bad-boy picks are fairly affluent. I’ll blame my Connecticut upbringing on this. Come on, you found him hot. A self-made man, confident, fun, has a yacht AND a private jet, throws the best parties. . .also LEO.

But then you look inside and realize he’s a terrible father, husband, and person, not to mention he’s a drug addict/alcoholic. Some people are just rotten to the core, and he’s no exception. You don’t want to date a rotten person. To quote my dad, “you can change your socks but you can’t change people.”

4. Captain Hook from Peter Pan: The Villain

Seems fun. He has a sidekick and a ship. He’s a great dresser. Sure, he might have hair that’s nicer than yours (or is that wig? Unclear). And yeah, that hook could be problematic in the bedroom. But he has a sensitive side! He’s scared of crocodiles! Isn’t that adorable?

But, you don’t want to date this type, aside from the potential hook complications; he’s also a villain. I mean he tries to kill Peter Pan and the lost boys constantly. Yeah, don’t date murderers.

5. Bender from The Breakfast Club: The Convict

What do you think happened after he and Molly Ringwald’s character fell in love? Something tells me a lot of heartbreak. Yes, he’s fresh, he talks back to authority, and wears flannel like no one else. But the whole problem-with-authority factor could translate to unemployable. And you want to date someone with a job, or at least a drive for something.

6. Stanley from A Street Car Named Desire: The Animal

Played perfectly by Marlon Brando. This is passion, as he rips open his shirt revealing his perfectly chiseled chest howling for his love Stella into the night. Don’t you want that kind of romance?

There’s a fine line between passion and crazy. I’d stay away from crazy.

7. Patrick Batemen in American Psycho: The Psycho

He works on Wall Street, has a better beauty regimen than you, is a great dresser, he gets reservations at the best restaurants in town, and has a bone business card with Silian-Grail lettering. He really has it all. Except for the fact that he either killed a bunch of people or is just insane. Also, he’s not a nice person. He would make a terrible boyfriend. But maybe you can learn something from his morning routine.

7. Jim Stark in Rebel Without A Cause: The Rebel

He’s the classic bad boy; red leather jacket, a motorcycle, indeed a rebel without a cause. He’s become a role model for all rebels and bad-boy boys to follow. I really don’t see a downside for dating him aside from the fact that motorcycle helmets mess up your hair.

So there you have it. Bad-boy types you should avoid. Or go ahead and date them, but don’t say we didn’t warn you.

Images via , here, here, here, here, here here and here.

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