how much should a guy spend on a woman?

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I think at this point my attitude for courtesies is: if I'd do it for one person I'd do it for anyone. If I hold the door open for a guy and we're part of a group its not particularly weird or 'fruity', neither is it if I don't know the person behind me but I pass the edge of the door off to them. If I get a scowl or an odd reaction from a woman though - I write it off at that point, and admittedly it hasn't happened often, not even sure if its really happened anywhere in memory. I've had times too where when I was out with friends and owed a round of drinks they met up with maybe several girls, I'd buy a round, one of them might even ask "Wait, are you buying this for us because we're girls?", my answer: no, I owed a round, pleased to meet you, if you get me back later great, if not perhaps some other time. At least with that attitude I know that I'm doing right by myself and, if it's unproductive and its logical and self-centered enough to keep me single for a good while - great. I suppose my biggest concern is being true to myself though, IMO if I have to go out on a limb, disobey my own intuition, and then have to deal with both the positive and negative consequences of those decisions as if they were of my own heart - I have more of a problem with being successful that way than unsuccessful being who I really am.

The bartender likes the guy who always buys the drinks. He sometimes acts as your wingman.

And man, approaching a gaggle of women at a bar, it's hard to single one out of the group sometimes.

Lol, you're a better man than I. I wouldn't even try frying my brain like on a perfectly good night of drinking, hate that whole paradigm as well of having to make a blatantly concocted approach but have to also worry about making sure it doesn't look creeperish, or at least not *too* creeperish, etc.. For whatever reason the tradeoff's just never been there for me.