I always find the moment when the check comes to be awkward, even if I know he's paying. Does proper ettiquette require that I at least offer to pay, even if I know he will decline? I usually do, but now I am wondering, is that a bad move? Anybody have any suggestions?
I don't think it's a bad move. I actually think it's nice when a girl offers. If you did not offer, though, I would not think any less of you, especially if I asked you out, and not the other way around.
I agree with Mitchell but I'd also have to say, if you're going to offer, be prepared to actually do it. I offered once,on a first date, and had a guy actually take me up on it. Needless to say, I never went out with him again.
But that's where you women get confusing. Why would you offer to pay if you didn't want to? Maybe the guy thought you wanted to pay and it would be rude not to? Maybe he didn't want you to think he was a chauvanist or something!