Smart Women Tell Us Why They Date Crazy Men

Let’s be honest – no one thinks Charlie Sheen is sane at this point, right? Maybe 2% of the planet is saying “oh, yeah, he’s a rock star from Mars, that is a completely normal statement. Too bad he and I could not be friends because I’m a classical pianist from Venus.” The other 98% of us agree that he’s hopped a bus to Crazytown? Good.

But what about the goddesses? (Charlie’s two young girlfriends, international sensations?)

They appear to be standing by their man! But why would women stay with a man who seems so obviously less than stable? What’s the appeal to begin with? We checked in with various ladies (who I have made lady-flowers to protect their identities) to understand the allure of the madman.

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    • springchicken

      I dated a major crazy one time but the thing is if they’re really smart and charming, it can really mascarade as intense and complicated, at least for a while. We didn’t date for very long and I suspect I would have caught on if it had laster much longer As it was, a year after we broke it off he called me up for lunch and let me know that he’d joined a cult (my word not his, obvi) and that said they’d helped him realize that all of his problems in life could be traced back to an incident with a gerbil in his kindergarten classroom. That’s kind of when all the pieces came together.

    • Dan

      Maybe tey date them because they’re crazy too?

    • Kate

      In the Charlie Sheen case, anyway, maybe because he’s crazy-rich? And famous? And for some reason in this day and age American women are willing to do absolutely anything for their 15 minutes of infamy? Besides, I’m assuming you were taking a leap when CS’s two “goddesses” led you to think “smart women…..”

    • Ali

      Charlie sheen looks like such a huge douche in this picture!

    • Leah

      I really like the part about how smart women mistake bat-shit crazy men for emotionally complex. I’m going to use that as my excuse from now on, instead of “I have bad taste in men”. It sounds much better.

      And how interesting is it that it seems like everyone (or at least everyone who works at or reads The Gloss) has dated a crazy? Do you think that it’s a reality, or just that WE think they were crazy? And that we all identify as smart women?

      • Jennifer Wright

        I think that’s actually a really good point. Because honestly, whenever a man says “oh, I had to break up with her, she was CRAZY” what I hear is “I had to break up with her because she yelled at me when I didn’t return her calls for two weeks.” But we can agree that anyone who tries to blow up a church is actually crazy, right? (And, I guess I assume TheGloss readers/friends of staff are all smart women because I assume dumb women don’t see a picture of Yoda in a backpack and say “this is a site for me.” But the way we categorize smartness/dumbness is insanely subjective and based on things we personally value. There used to be this reality show called Beauty and the Geek wherein “smart guys” were paired with “dumb girls”. I love this one scene where the girls had to teach the guy about hair care products, one guy had no idea what conditioner was and the girl’s expression clearly read “geez, you’re an idiot.” But this is another topic altogether. Maybe one worth discssing! I don’t know!)

      • Leah

        I think you’re on to something there with the subjective part. We all perceive sanity differently. And what about someone who goes a little crazy because of specific triggers? What if they’re only crazy in certain situations? Sometimes it seems like both sexes play the “he/she was NUTS” card because it’s easier to just say that someone was crazy than it is to explain the complexities of why a relationship didn’t work out.

    • Inna

      I think smart women like crazy guys because they’re free in a way. They don’t follow social norms and they’re non-conformists, they are usually intelligent and unlike most “normal” guys, who sometimes seem to have no feelings at all, their craziness qualifies them instantly as emotionally intelligent and as people who listen to themselves and really follow their hearts (even if the way they’re going ends in no good, but you can always make them understand that, right?). Basically, smart, deep, daring (you have to be all three to dig into yourself enough to go nuts, right?) and most fun: Unpredictable. Yes, I get the appeal.

    • Emily

      Violet hit the nail on the head.

    • Reems

      I 100% agree with Rose. I dated a bipolar guy who at first completely swept me off my feet by leaving me trails of roses and being utterly romantic, attentive and sweet. But one day he bought a plane ticket to Israel and decided he was running away to “find out what Jesus was all about”. At this point I realized he was bat-shit insane and broke it off. He lasted in Israel for about 3 months then moved back in with his mother until I ran into him on the street one day and he publicly attacked me. True story.

      • Michael McLendon

        Hello, I am a dude who may have dated a bipolar woman. She revealed on the second date that wellibutrin was her prescribed drug while downing the third cocktail. The conversation was exhausting relative to her rambling about family and then of course a short crying episode. My instincts seemed to be telling me that something isn’t right.

        She wanted to be physical on the second date and was put off by my inclination to treat her like a lady. Too much too soon was a common theme for the date. After the date, I was relieved she was on her way home.

        Like you, I have dated someone who is batshit crazy. It is especially sad when you are attracted to the person.

      • LR

        Any woman who makes the first move and initiates sex is a slut to you. You want her to be aloof, mysterious, cold, indifferent, and quiet. @Inna-Normal women don’t have nor express feelings at all because it’s unfeminine.

      • theman123


        So him going to Israel to find Christ, made him crazy? So in other words, him having a religion, made him crazy? Jeez I guess 3 billion people are crazy then. Christianity is only the biggest religion in the world. In fact, the majority of people need to believe in an afterlife, its part of human awareness- knowing we are going to die is tough. In my opinion, you’d have to be a little insane to look at death and shrug without caring at all. Know what I mean?

        The part about him attacking you is crazy, yes. But part of me feels like you just made that up to make Christians look bad. Also, its rude to dump somebody just because they get religious. Its HIS religion, not YOURS. You dont have a right to tell him what he can believe in. Sheeessshhh

      • bigman123

        Somehow when you say “attack”, I feel like you mean he “verbally said some things you dont like”. When you are trying to have us believe that he physically assaulted you.

    • LR

      11 Reasons Why Chicks Love Crazy Dudes should be the title. Society thinks it’s okay for men to be crazy and that crazy men are masculine