Long time lurker, first time poster.

I've been flirting with an HB10 at work for some time now. I made a bet with her that if I could get something done, she would buy me dinner. If I didn't get it done, I would buy her dinner. I lost.

Anyway, she asked me if she could take me to dinner anyway and suggested Friday night. I told her I'd pick her up. Then she got real cold. I'm guessing it's because she wants to meet me somehwere because she lives with her BF (she doesn't know I know she has a BF. She is actively avoiding telling me about him).

What's my next move? Logic says I should not press the issue so I don't seem needy. It's Wednesday now. Wait until next Friday then casually mention it? Or do you think I can bring it up as soon as this Friday morning and just casually ask again?

Thanks for the help!

Relax. She's probably thinking of a sensible solution to the problem she's facing.

Your best bet is to never bring it up again and wait for her to get back to you. If she never gets back to you before the date was supposed to take place, then so be it. At least after that, in say 3 weeks time, you'll be able to say something like "hey, weren't you supposed to get me dinner a while back or something?"

If the date ends up taking place as I suspect it may, you should insist on paying for the dinner... And no, it wouldn't be beta. Why? Because you, in a sense, are bound by the terms of the deal you made with her. You are being loyal and respecting the rules of the deal you made. So you pay. Follow the waiter to the cash with your credit card if she insists on paying. This will put a few points in your bank.

Thanks for the input. I was thinking along the same lines. Anyone else have suggestions?

Well, shit. She just texted me ":-)" at 10:45 PM.

Still not exactly sure how to proceed. Should I txt back tonight or wait to talk to her tomorrow?

I've been really good about over analyzing up until right now. Go figure.

Do what you would usually do if you were to receive a smiley face.

But personally, I would simply ignore it because let's face it... What the fuck are you supposed to do with that? Although everyone has his own game...

I asked 'did you figure out if Friday worked for you?'. Probably not the best move, but too late now. I won't push any more though. If I get no response then I'll just ignore it for a few weeks.