Dating A Mean Boy

Mean boys will try to destroy you. You won’t know it at first. They’ll just seem like they’re cocky (SEXY), assertive (SO SEXY), and a “real man” (Oh my god, I’m pregnant just thinking about it!). But once they have you and know you’re exclusive, they will transform into something ugly. It will be false advertising and maybe you’ll wonder if you can get your money back because this is not what you ordered at the relationship buffet! But it’s too late. You’re in it. You’re dating a mean boy whose sole purpose is to make you feel the opposite of loved, to break you down and have you need them to get back up. You’ll know it the second they make a passing comment about your weight, your clothing choices or get mad at you for something completely trivial. You’ll know it the second their body winces when you go in for a kiss. “Uh oh, I’ve got a mean one again.”

No one is truly invincible to the mean boy. Sure, certain types of people are more prone to get into relationships with them. I’m talking about the girls with low self-esteem who want to have someone reinforce the awful things they already feel about themselves. I’m talking about the girls who mistake possessiveness for love. But anyone can end up with an asshole, at least for a little while. Anyone can find themselves dating someone beneath them. The strongest smartest women can end up with a mean boy. Why? Because people never make sense in love. They make sense in their work, with their friends and family, but when it comes to relationships, they can gravitate towards absolute trainwrecks. They can take everything they stand for, everything they represent, and cut it up into a million pieces.

Cold men are viewed as challenges. We think we can just warm them up in the oven, bring some color back into their cheeks and feed them chicken noodle soup, and everything will be so much better. We think that by offering them a certain kind of love, their coldness will begin to thaw and prove to be no match for your kindness. It never really works that way though. In the back of our minds, we know this. We know the endings before we even see the beginnings but it doesn’t really matter. You’re going to pursue the people you’re attracted to, regardless of any previous lessons you may have learned. If you’re more comfortable with meanness, that’s the type of man you’re going to end up with until it becomes uncomfortable and you realize you deserve better.

Mean boys will try to make you unfit for any other kind of man. They’re going to want to break you in a way that will make you undesirable to the good men. This is the part where you’re supposed to put your foot down and be like, “NEVER.” Perhaps the only good part about dating a mean boy is letting them know that they’re not who they thought you once were. “Sorry. You picked the wrong girl! Try someone else who will actually put up with your bullshit.” There is a breaking point you’ll reach. It’ll be like regaining consciousness after being in a coma for x amount of months, and years later when you look back at the relationship, it will be hard to understand how it could’ve actually happened. That wasn’t you, it was some low-rent stand-in version of yourself. No, seriously. THAT WAS NOT YOU.

You’ll hate the mean boy. You’ll hate yourself more for awhile afterwards but eventually, you’ll always blame them. You’ll never blame yourself. That’s the goal anyway. That’s the dream. Some people never figure it out and it’s a sad terrible thing. But you won’t be one of those, right? You’ll be one of the people who just got lost for a bit on the relationship path and ended up in Douchebag USA. I”t’s okay”, people will tell you, “everyone takes a detour there at some point. I’m just glad you found your way back.” TC mark

image – American Psycho

Ryan O'Connell

I'm a brat.


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  • Guest

    Someone’s gotta tell this kid to stop.

    • NoSexCity

      Seeing how it’s his website (I think), you’re probably SOL buddy.

  • Greg Petliski

    You’re such a chick Ryan.

  • Greg

    It seems most women can stand douchebags if they dress well/ look  beautiful

    • internetstranger

      whoa! Sexism AND a sort of sidelong nod at the “nice guys don’t get none” fallacy in one line. You are very efficient!

      • Greg

        He’s not incorrect though. I know tons of girls in my own life who fall in this category

      • Guest

        So sorry Greg, you forgot to log out before responding to your own comment.

      • Pirate


        The same goes for guys though. How many guys date ridiculously difficult and selfish hot bitches?

  • Grace Ruttenberg

    100% true

  • Guest

    what is the distinction between mean boy and nice boy? Everyone is mean sometimes, unless you’re like Mr. Rogers, and NO ONE wanted to fuck Mr. Rogers..

  • hunter ray

    I like how you wrote from the lady perspective, but I think that there are shit ton of mean gay boyzzzzzzzz

  • Rainbow Couch

    Love it.

  • Tabitha

    But what if you’re the mean girl? D;

  • Leighannaworkman

    I’m in one right now. I live with him. Agh!

  • Naiomi5

    Playing the blame game is wrong. If one doesn’t accept and acknowledge their contributions to the relationship, they’ll just end up in the same situation again.

  • the sexiest guest

    rude boy boy is you big enough? TAKE IT TAKE IT TAKE IT LOVE ME LOVE ME!!

  • Jordan

    I like this.  As long as we’re using mean, bad, douche as adjectives, this is it.  Bottom line.

  • Sexybitch


  • guesty

    I’m really mean sometimes and I hate it about myself.  

    • the sexiest guest

      don’t worry my dear guesty, *pats on back*.. I’m sure there are worse things than realizing that you’ve been treating people like garbage and destroying everything your whole life. there, there..

      • Guesty


  • the sexiest guest

    mean boys are fun in bed..i love getting spanked so hard my ass throbs and being called a hot fucking bitch while giving a blowjob

    • Vix

      yeah, but there’s a difference between playing in bed, and actually being a manipulative asshole. some of the nicest dude i’ve dated have been kinky bastards in the sheets ;)

      • the sexiest guest

        ha. my previous comment was completely sarcastic..

  • Anonymous

    Hell yeah! This is spot-on, Ryan.

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