To completely mess up a golden opportunity to secks a wimmen.
This guy completely Wozzed it:
"So I've known this girl for several months, but I'm not necessarily close with her by any means. She's flying into town and needs a ride afterward, so I offer to help. In exchange she offers to buy me dinner and pay for gas.
Now, a little background. When we first met, she was flirty with me when we saw each other at parties (what girl isn't, right?) but I wasn't particularly interested at the time because I had another girl in mind. We still talked on occasion etc, but she eventually started seeing this other guy "unofficially." I vaguely knew of this, but the matter was never discussed between us.
Back on target, we get to the restaurant (a fairly fancy place that she had picked out) and we're just making small talk (talking about her trip, etc) when about halfway through she casually drops "Oh, ______ and I broke up. I mean, I guess we weren't ever really dating but..." to which I think I said "Oh, I'm sorry to hear that." or something. Small talk continued and dinner went well.
We get back to her apartment early in the evening and I help her move her bags up. After we're inside she says "Oh, I've got these great pictures of us from _____ (a party we were both at)" which we look at. I notice that she skips by the pictures with "former boyfriend" pretty quickly.
I hear about a party nearby and invite her along, and we head out. Mild drinking ensues, but she's obviously tired from her plane flight and isn't having the greatest time, so I offer to drive her back home. As she gets out of the car she says "Call me about lunch tomorrow" and we exchange good nights.
Now that you've all been bored to death with my life, what's your opinion on this? I think I'm reading too much into the situation and she was just making small-talk. Then again, we have never before discussed anything about relationships, so I wouldn't have considered us friends on that level.
Normally I'd just ask her out for real and get it over with, but we've got lots of mutual friends, and I'd rather not make encounters awkward in the future if I'm misreading this now."