I've always been of the mind that as a guy, you don't ask out waitresses. No matter how hot they are, no matter how much your convinced they're into you, don't ask them out. For two reasons: 1) Part of being a waitress (at least at swanky places where the waitresses are hired because they're attractive), being a little flirty and sending smiles is all part of the job. It increases their tips. And as a guy, I can say yes, it does work. 2) Even if they are into you, you'd still be just another guy at the bar who asks them out. How tacky... But lately I've had a few really cute waitresses who actually seem into me (I've accepted the fact I'm attractive, because of attention and straight up comments I get, but I'm generally shy and reserved). Should I stick by my previous philosophy, or should I go out on a limb and ask one out? Comments from waitresses and your experiences with this sort of thing would be appreciated.