Haha, it wasn't that big of a deal, for whatever reason or motive she just decided to pay for my order. Afterwards, though, I ended up buying someone else's drink, so it was a "pay it forward" deal regardless. I guess I hope it was cause she dug me:D couldnt be more than a two or three years older than me, I'm certainly not complaining. That's pretty awesome, props to you for not factoring that into the equation of something so much more simple as just being attracted to her. I'll be there next Sunday, we'll see if she is! I certainly have a talking point to open on.My wife is 7 years older than me. That perceived problem will solve itself; you aren't getting any younger :)
Do it. I know there is some conventional wisdom out there about not trying to date bartenders/waitresses/servicestaff because they're sick of getting hit on all day and they probably aren't interested anway, etc. But I've dated multiple baristas and bartenders in my day. Sometimes they really do like you and you like them. Don't have to be the guy hitting on the staff, but she did buy you a drink...I don't think you could be faulted for floating the possibility of catching a show or something :P