Dear Dumb Guy: I’m a database analyst for a large insurance company. I’ve worked the graveyard shift for almost ten years and the most exciting thing that ever happened was when there was a blackout one night, me and Tom, my co-worker, pushed our cubicle walls together and pretended like we were in the trash compactor in Star Wars for the entire shift.

Anyway, Tom quit and was replaced, last month, by a girl! I think she’s like cute and all and I think she totally has the hots for me because I showed her a cool workaround for a bugfix she was dealing with. Here’s my question – I’m thinking of asking her out, and when she says yes, I’m wondering how long I should wait until I try for first base? – Clueless in Cubicleland

Dear Cubicleland: Dude, first of all, that Star Wars thing is TOTALLY BADASS. Next week, when my furlough is up and I’m back at the newspaper, we are totally gonna do that one day!

Anyways, to your point about how quick to move with the girl of your nerdcore dreams. Most of the women that I’ve encountered in, shall we say, “social situations,” were fast movers. That is to say, the distance between home plate and first base was about one full stride, and second and third bases were actually stacked on top of one another. And they were out in the grass, off to the right, over there by the foul line. Trust me, as a metaphor it makes perfect sense, and that’s what a meta is phor.

GAAAAAHAHAHAHA! I am so damn funny sometimes.

So, anyway, here’s all I’m saying: Go in with confidence, with swagger, with the attitude and determination that comes from taking a good solid shower and tucking your shirt in. Take her to dinner. Then it’s all about timing. I find that women are most susceptible to romantic wooing right after the potato skins are down the hatch. Look her in the eyes, crack just the tiniest bit of a winsome and rakish smile, and say something really really romantic and erotic, like “Hey, what do you say we go do some non-Facebook poking?”

There isn’t a woman alive who wouldn’t turn to jelly at such a moment.