I’ve known this girl I like for a while, and I want to tell her I’m crazy about her. We’re really close, and one thing I know about her (because she’s admitted to it) is that she loves what she can’t have. As soon as she’s got it, she doesn’t want it anymore. If she knows a guy likes her, most of his appeal to her vanished and when she goes out with a guy she’s wanted, she loses interest quickly. What do I do?
–Curious Guy

There are a lot of girls that will say that, but it’s really not true. They just don’t know what they want. They think they like Billy because he’s so awesome, but once they date Billy and the novelty wears off, they find that the substance isn’t enough to keep them entertained. It’s hard to date a woman who doesn’t know what she wants, because inevitably, what she wants isn’t you. Unless she’s the kind of woman that’s constantly looking for something new and different. In which case, she probably has committment issues or “the grass is greener” issues. She thinks she deserves more than what she has. That’s harder. Here’s a simple way of solving this. Ask her, “would you ever date a guy like me?” See what she says. See what she thinks. She may not be ready to date someone that’s really into her, or she may be getting to a point in her life where she’s willing to re-examine what her value system is. I find that value systems are a sign of maturity.

I once shagged this guy who was really into me because I was Mexican/Colombian. He thought that was the hottest thing ever. I was very aware that that was the value he was using, and that once the novelty wore off, I’d be Adri, filled with insecurites and a whole lot of fun. And maybe that’s not what he wanted. But maybe in five years, his value system will have altered, and he’ll be more interested in smart, sexy, Mexican/Colombians. Or something. I’m not sure that tangent really fit the situation. So let’s start over: I’ve dated dudes for stupid reasons. Dudes have dated me for stupid reasons. At some point, we all get to a point where we decide to cut the bullshit and be honest and vulnerable to another. She may not be ready to do that in her life. If you really want her, take a chance now or wait till you know she’s ready. But be careful, she may be gone or with someone else by the time you get around to it. On that note… fuck it. Bobby Kittleman, wherever you are, you should know I had a crush on you in high school. I never told you because I thought you would laugh in my face. I thought you were swell. I’m so over it now. So, my advice, Curious Guy, is to follow your gut. Take your head out of the equation, get ready for total heartache and humiliation, and do it. Tell her she’s great. Because who the fuck knows, maybe she’s just waiting for you to grow the balls to ask her out. Or maybe she’ll laugh in your face. Either way, let me know how it goes.