On goal-oriented dating

I’m in my last year at a good university, enjoying life and getting excited about heading out into the professional world. My biggest insecurity is that I’ve never had a relationship that’s lasted longer than a month. In high school, I was a late bloomer in the dating scene and never even hooked up with someone until the summer before Senior year. Most of my “relationships” (if you want to call them that) have been with girls whose company I enjoy but the chemistry just never seems right. I just can’t seem to find the right girl that I’m both attracted to and has a personality that matches mine. I’m an attractive, social guy, and I don’t put out the desperate vibe – I feel like it’s just circumstance that I haven’t found anyone. But it’s gotten to the point that it really bothers me. I feel like college is a time when I am surrounded by people my own age and of similar intelligence – if I graduate without having had a single meaningful relationship, I’m going to be pretty unhappy. Am I being overly analytical? Should I be less picky?

You don’t need to be less picky. You need to be in less of a hurry. Your problem isn’t that you’re being overly analytical. It’s that you’ve got a ridiculous master plan for your life that includes charts and graphs and a timetable.

I know your type. There’s a voice in the back of your head constantly reminding you that you’re supposed to be married with 2.5 kids and a golden retriever by the time you’re in your mid-thirties. This voice says you’re supposed to date around for a few years before you find the perfect girl and settle down. It says you’re supposed to be in a stable, long-term relationship for a couple years before you get married, and it says you’re supposed to be married for a little while before you start having kids.

This voice in the back of your head (which sounds suspiciously like your mother) has already done the math, and quite frankly, it’s a little disappointed that you didn’t find your future wife during college. Well, guess what, skipper? You need to tell that voice to shut the fuck up, or you’re gonna end up leading a miserable life.

You’re wrong about what will make you unhappy. It isn’t the fact that you might graduate without having had a single meaningful relationship. It’s that you’re blind to the fact that regardless how long they’ve lasted, all of your relationships have been meaningful.

Every random hookup, every super cool chick you weren’t really attracted to, every potential girlfriend that fizzled after the third date — all of them count as meaningful relationships, especially during your college years.

Your single biggest mistake is that you think you have to find the right girl and spend a predetermined amount of time in a relationship before it counts as meaningful. (I’m guessing with you, it’s probably three months.)

Do yourself a huge favor and throw the timetable and your “right girl” checklist out the window. Stop being so damned goal-oriented with your dating. Come on, man. You’re in your early twenties. Smell some fucking roses already.

(Check out my latest column over at Playboy, and fellas, feel free to send me your questions at


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