I can’t even remember whose girl that was - was it Demon’s?

It’s always awkward when you run into a friend’s daughter on your OKCupid quivermatches. Especially when you knew her when she was 14, and never much cared for her.

So I need some advice (or, more likely, ridicule).

It’s not exactly internet dating related, but it seems like the thread has already moved outside that realm.

Anyways, there’s this girl at school I’ve gotten to know somewhat over the past few months and I’d really like to ask out. We sometimes sat next to each other in class in the spring. It turns ot we’re in the same major (GIS). This semester I work as the GIS Lab technician, so I see her at least twice a week. We make small talk, I help her with some schoolwork, etc. I’m 99% sure there’s no boyfriend, and I’ve made it clear I’m not attached. She looks like a slightly more Hispanic Lea Michele - which is to say, she’s stunning.

So lately I’ve gotten some good signals. She’s written a few “Hi” message on the white-board in the lab, we have some (short) non-school related conversations, and she even pinged me via our in-house e-mail system a few days ago (it’s G-Mail, actually). We chatted for a few minutes, then she ended it rather abruptly.

This weekend is the only I’ll have free for, basically, the rest of 2010. So I was going to make my move. But there’s a problem - I totally wussed out. I kind of had a chance, but there were others in the lab, and I felt awkward. I guess I could have done the delayed “follow her into hall” thing - but I’m horrible at this and so I didn’t.

My recovery attempt was to e-mail her with a follow-up to something I was helping her with today . . . I then gave my number and told her to call if she had questions, just wanted to talk, or was bored this weekend and wanted to hang-out. It hit me how lame that sounded about 5 minutes after I hit Send. I should have just sacked-up eariler today and asked her.

So tell me QT3 - Did I fuck this up?

Nah, nothing’s fucked up. It’s not even that lame; I can’t imagine any woman running for the hills from something as tame as that. When will you see her in person again? Ask her out then. When you say you have no time free, do you actually mean it? I would make the time for a hot date.

No, you did fine. Fucking up would have been sending another e-mail in some sort of sociopathic bashful tone clarifying what you meant.

You should have sacked up. “Want to hang out this weekend? Grab something to eat?” and throw a smile out.

You didn’t “fuck it up” in the sense of blowing your chance, but I don’t think you did much to advance things either. I’d say that you should come up with something you want to do with her and then either the next time you see her, when she responds to your email, or sometime tomorrow afternoon if neither of those have happened yet, just tell her, “I’d like to do X with you on Sat.” Clear invitation, something more concrete than an open-ended “let’s hang out” and no pressure on her to come up with a plan/date/time.

I must be missing something. Weren’t you married earlier this year? Not to pry or anything, but…

There’s gotta be a better way to ask that.

I apologize for dredging anything up that I shouldn’t be.

It ended in January, but was headed downhill long before that.

Sorry to hear that, man.

You should give her homemade cards with your picture glued on them telling her that she’s the one.

Angie makes the best ones.

GET OUT. GET OUT NOW.

The way to do this is to have something going on, ski trip, barbeque, hiking, whatever. Bring it up in conversation, very likely she’ll say something like “Oh, I’ve never done that.” or “I like to do that.” Then you say “Hey, you want to go with me this weekend to do X?”

Best possible thing is something where you have to drive 45 minutes or so to get there. Long enough to chat, not too long you’ll gnaw your arm off if it doesn’t work out.

H.

That’s a pretty contrived scenario! If you already had something planned I guess it could work, but I prefer my first dates to not involve 45 minutes of driving.

It’s not the worst thing. What you want to do on a first date is talk as much as possible to find things out about the other person - being in a car for 45 minutes seems like a good time to do that. On the way back you can talk about the stuff you just did. Seems reasonable to me!

Or, you know, you could get coffee or something.

You mean there are other options besides the 45 minute car ride one? I’m shocked.

My point was that if you’re not certain if she’s interested, then a neutral activity is a good way to get a better grasp of her position and to get to know her better. Going and getting coffee certainly works, but since it’s only about two people and conversation, is more of a “date” setting and some folks aren’t as comfortable with that.

H.

And if you like her, you could “run out of gas.”

You could take her on a 45 minute boat ride. You almost always get lucky in this scenario, because of the implications.