Having been one of the cooks in the back with lots of big knives at my disposal, and having been a customer to some incredibly hawt waitresses, I still think open and honest is the way to go- but there are some things to keep in mind.


Just like most women know to flirt with the bartender, most waitresses know to be smiling, upbeat, and nice just short of flirting if they want a good tip from a guy. It's part of the job- doing this will *directly* affect your tips, which are usually 80% or more of your income. Keeping in mind that the ladies (or men) in question are being nice and friendly as a part of their job first and foremost, I am wary of asking a waitress out. I'll usually be upfront about it though (I have in the past anyway), and at least tell her how much I enjoy her company, and ask if she would like to get together sometime when she's not working. If she's being professionally nice, there will be excuses- take them gallantly and bother her about it no more! Enjoy the company and be gracious, she might already have a boyfriend- or husband- but not want that to interfere with her tips. This is not deceitful, it is logical.

Bottom line, I'd say, is be honest. I like the fact that the OP was upfront about it. The ball is in her court now. The fact that there may be a history of other men doing such things and becoming stalker-ish is a strike against you, but those people aren't you. Treat her the way you'd like to be treated- honestly, and with respect. Isn't that what we all want?