The act of sitting at a restaurant or bar table (particlularly a Hooters type establishment) and seeing if your waitress is the best one there or not. Winning the waitress lottery often involves getting the prettiest waitress, but it can also mean getting the friendliest one or simply the one who is most efficient.
Guyl 1: Dang it! All these hot chicks in here and we got the waitress who's built like a linebacker. That stinks.
Guy 2: Yeah, we definitely lost the Waitress Lottery, but at least we've got cold beer and eye candy all around us to enjoy.
When she came over I thought we'd won the waitress lottery, cause she's a hottie. We've been waiting forever for our beer, so I guess we didn't.