Long story short, one of my long-time friends has been working with this HB8 for the last few months and every time I hang out with him, he constantly tells me how well me and her would get along. Tonight I finally got a chance to meet her with my friend and a large number of both of their coworkers for happy hour. Given that we were all at the same table, I didn't want to try anything too aggressive or obvious in my approach but she and I definitely hit it off extremely well despite it being a semi-work environment (she ended up being 30 mins late to dinner with a friend cause we were talking so much). I ended up securing a follow-up meeting via making a dinner bet which she lost and now has to buy me dinner.

We already picked out the restaurant, but my only question is should I actually let her go through with paying for the whole thing? My thought was to do something like "you got this one since you lost the bet, I'll get the next one" because I actually am interested in pursuing a LTR with her, but is there any sense in me paying half? I just feel a little awkward with her paying for the whole thing, even though she did lose the bet

^I agree, I guess what I'm worried about is the reverse of the stigma where you take a girl out and she automatically expects you to pay for everything and you think of her as a golddigger and never call her again. Well in this case, am worried she's just going to think I'm cheap and may hold that against me in the future (which I can combat by setting up a future date where I agree to pay, but still).

Even though I have as good of an excuse as you can get to not pay by winning the bet, I just feel like there's going to be that awkward moment when she's signing for the check where she thinks to herself "wow I can't believe he actually made me pay for this, I thought he was kidding around". At the same time, if I do pay for any of it, it could potentially show little backbone and sets a bad precedent for the future, so either way it's potentially bad

More thoughts?

I would say that since she lost the bet, she should pay. You may want to pay the tip though. You can always arrange for a day 3 as well and hint that you will treat her to that date. Good luck!

Hey man,

She lost the bet fair and square. Don't feel guilty what so ever. If you give her value in return for her buying you dinner, I promise this won't be the only the time she'll buy you stuff.

What I mean by that is, if she enjoys your company(which she already has), and benefits from being around you, than you are giving her value, which is priceless.

This, I believe, is the most fundamental thing that AFC's will never understand. VALUE.

Even if you don't believe this whole VALUE thing, at least frame the situation into thinking about why SHOULDN'T she pay for you. Let's be honest, if some ugly girl invited you out to dinner and she said she would pay, i'm pretty sure you would't be having this dilemma.

Man up and get used to girls paying for your shit...

LAST NOTE: Jennifer Lopez gives her boyfriend 10,000$ a week, just for the heck of it.

Let that sink in for a bit, and than ask yourself again if you feel guilty about letting her pay.