Centerstage - Chicago's Original City Guide

I've got a unique situation. I'm 35, and never had much dating experience or any sex. Most of my 20's, I spent in bed, barely able to do much of anything. I worked until I couldn't. I just had experimental brain surgery to help me. It's like 10 or 15 years of my life is missing; I even look very young, having not lived much. To everyone on the street, I'm just some random 20-something now. I have no close friends or acquaintances to ask questions, so my question is, how do I go about dating? Should I be upfront and scare everyone off or try the impossible and somehow cover for a while without lying? Would women even be interested in me? Do I admit that I don't know anything?

~Joe

Is this another one of those experimental brain surgery dating questions? Shee-eesh. Who do I look like, Tyra Banks?

I don’t know where all this "honesty" crap comes from. (I'm looking at you, Billy Joel!) It's a date, not the SAT. Imagine if someone you just met said to you: "Hi, I'm Tammy. I'm an Insurance Adjuster who makes $30K a year. I've slept with 9 people and cheated on at least one boyfriend while wasted. I also collect Thundercats figurines. Pass me a Swedish fish?"

You've got a better chance of not freaking someone out if you divulge information about yourself slowly, at a natural pace, otherwise you'll come off like a leper. (I hope you aren't actually a leper, though you were kind of vague about the whole "brain surgery" thing. If so, consider this my apology.) Plus, confessing to strangers amounts to conversational masturbation. And that's just bad form.

Take this to heart, Joe. You don't have to tell anyone anything you're not comfortable with, especially lack of experience, which isn't a flaw. David Hasselhoff tattoo? Flaw. Using the term "feminazi"? Flaw. Listening to Dave Matthews Band post-2002? Flaw. Not dating half the girls in Wrigleyville? Not a flaw. Make sense? This isn't to say you should lie about your life or past experiences, because it's all going to come out eventually, but as you are getting to know someone, play up all your best physical and personality traits, and do your best to minimize your less attractive ones. If you present your situation as not that big of a deal, then it won't be a big deal.

I know plenty of guys who've had tons of dating experience. And you know what? They are still assholes. It's your job to not be like them. Here's how. Show up, be attentive, respectful, confident. Be interested in what they are saying.

Remember, this isn't brain surgery; it's drinks. Or bowling. Or Wrigleyville orgies. What?