Originally Posted by
TheEvilJester
I will start off by saying this.... she's a waitress. So it is part of her job to be nice to the customer. So, based just on the interaction you had with her while you were there, I would not jump to the conclusion that there was any mutual interest. Don't get me wrong. I'm not saying there definitely wasn't. There could have been. It's not like you cease to be a human being while you are at work. Even though she is a waitress, she would still find some people attractive, and might sometimes find customers attractive.
So, it could be entirely possible there was mutual interest, it's just that, if I were you, I'd just assume it was just her doing her job. That said, that doesn't mean you can't chat her up and even ask her out if you are interested. Honestly, I don't think there is anything wrong with the direct approach, with just asking her out.....
However, it doesn't sound like you feel comfortable with that approach. Believe me, I am the same way. I am NOT at all the type to just go up to a woman I find attractive and ask her out. It just feels too icky to me like it makes me look like one of "those guys" who just hits on anything that moves. Nothing could be further from the truth for me. So, like you, I prefer to at least talk a little first to at least get a feel for if this particular woman seems to enjoy my company. ....Unfortunately I am too ridiculously shy even for that... but that's my burden.
In your case, if you feel comfortable with it, just chat with her a little. Honestly, WHAT you talk about really doesn't matter. (You know... within reason. LOL!) Just chat. Maybe ask her a little about her. Remember, also, that she is at work. You can't necessarily gab her ear off for long, but you can ask her a few questions about her. Then, maybe right before you leave just grab her and say something like "Hey, it was really nice talking to you. I'd actually enjoy getting together outside of the restaurant if you'd like that." Then either ask for her number or give her yours (I'm not really sure which you are supposed to do these days.)
Though, if you do have friends who are servers, they can probably offer you more advice as to how to approach it. Good luck to you!