talking with someone as an aquaintence of friend is different from dating someone. People can really misrepresent themselves when they want to.
I used to serve tables at a fancy restaurant and I hate people. But my regulars thought I really liked them. NOPE!
Girls are even shallower than men in the "tipping" industries. I'd watch out if I were you. You can probably get a much better girl, like a dancer, just not an exotic one...
It really depends, I say go for it because the rewards are good, just be very very careful.