Dear Dategirl, I am a hopeless geek. I like comics, cosplay, video

Dear Dategirl,

I am a hopeless geek. I like comics, cosplay, video games, and even sometimes D&D. I am 37 years old, and haven’t had sex since I was 29. I’m a bit overweight, but I have a great-paying job in IT and I’m a nice guy. I went on a date last night with a pretty girl nerd graphic designer who stuck her hand out for a shake when I tried to kiss her goodnight. Not the first time, though I usually get the cheek.

When I asked the last girl I tried to date (before last night) what she thought was wrong with me, she said I was just too “nice.”

I may wear glasses and not dress up very often, but my nerd-ass friends like me and think I’m funny. I don’t drink, smoke, or do drugs, but when I see cute nerd girls at Comicon and gaming conventions, they’re always with their boyfriends who are just as nerdy as me! Where do these girls look for dates? I am an Internet whiz and I can’t fucking find them!

—Proud Nerd

Please don’t ever ask someone you want to fuck what’s wrong with you. Even if she was just having an off night and fully intended to blow you the next time she saw you, that question just negated any possibility of you ever getting laid. Just imagining how that scenario went down is excruciating. Let’s forget it ever happened, OK?

Even though we’ve never met, I’ll tell you right now the problem isn’t that you’re “too nice”; it’s that you’re the kind of guy who would ask a stranger such a question. Where’s your swagger? Where’s your sense of mystery? You showed her your ass (figuratively) before you ever saw hers. WRONG!

Take off the Watchman T-shirt and buy three oxfords: one white, another navy . . . the third, I’ll let you pick the color. Maybe a plaid. While you’re at the store—nothing more low-end than Gap, please—pick up a pair of pants that don’t fit like you’ve got a load in your diaper. Ditch those ratty sneaks and buy some non-fug footwear. Oh, and underwear. Boxer briefs. Anything in your drawers drawer with a hole or a smear gets pitched.

How do I know your wardrobe is a revolving collection of stained novelty T-shirts, ill-fitting jeans, and sneakers? Let’s just say I’ve dated your demographic. Oh, and if your skin is wonky, get to a dermatologist. Change your sheets and pillowcases no more infrequently than twice a month. Start working out once in a while—you don’t have to be super-fit, you just need to generate some confidence and endorphins.

Once you’ve ditched the schleprock persona, practice talking to girls. Seriously, we’re just like “people,” only we smell better and pee sitting down. Start with completely non-threatening women, like elderly drugstore clerks or the lady at the donut store. Work your way up to waitresses before you go into the lions’ den that is chatting up the bartender. (Seriously—not for amateurs.)

Once you’re able to talk to women who are paid to be nice to you, go online and ask someone on a date. Don’t hedge—tell her you want to take her to dinner, and go somewhere that doesn’t have a drive-thru component. Compliment something unusual, like a piece of jewelry or her socks. (Not her boobs.) Ask her questions and listen to the answers. Kiss her, and if she gives you the cheek, move on.

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