So, I want to open on a cute and shy waitress.

She works in a busy restaurant -- really great food which is why I go there so much -- but the waitress is extremely shy around me. She usually stands far back from me when she takes my order, tries to hide her smile and gives me longing looks. She doesn't act this way around others when taking their orders and i've been sure not to hit on her in any shape or form but given the interest she seems to have in me i'm thinking of going for it. How do I approach this situation? Should I go for it or follow the age old adage "Don't shit where you eat"?

I personally think it's fine to shit where you eat in this instance. It's not like you work with this person - even if you do see them once in a while, so you're not violating any professional boundaries...

If she's shy I'd stay away from negs or deprecating humor - even if you're decent with delivery.

Shy chicks need safe, slow going...

Maybe try and get personal or tell her you're in there all the time and that she always looks great and provides great service. Could take a couple visits to get her really used to you and chatty...

Talk her up and try some light kino if it's appropriate. Graduate into "you know I've been thinking of asking you this for weeks so I'm just going to do it: I think you're great and I'd really like to get to know you better over a drink"

My 2 cents... Good luck, buddy!

Thanks for the advice.

I was kind of hoping for something a bit more "immediate" as opposed to over a time period and progressively working towards it. Of course I would want to do something safe so I can go back there without making it awkward for either party.