The biggest myth to picking up waitresses is that they are “hard to pick up.” I believe the only guys who say that are ones who have never tried, because waitresses are the most receptive to game. To be a waitress means you have to be outgoing and friendly, qualities that go well with pick up artists so they need a receptive girl in order to deliver their game.
One thing that doesn’t work on waitresses is showing off with money. Chances are she gets it a dozen times a day and eventually it becomes hard for her to distinguish all the guys that are hinting at how much money they make. If you want to pick up a waitress the best angle to take is “poor service” angle. Let me explain…
You want to tease her that the service is not that great. For example she’ll bring you a drink and you joke, “This drink doesn’t have enough ice… the service here is really bad.” You say this with a smile on your face. That’s the key! She knows you’re just fucking around.
Later say that you and your friend want to change waitresses with one who is more “warm and affectionate.” The idea is to bust her balls that she isn’t trying hard enough. Waitresses are very receptive to this type of game. Try it.
You should get to the point where you are having longer and longer conversation each time she comes to your table. If the restaurant is busy then this is going to be hard to accomplish because she simply won’t have the time to chat, but otherwise she may stick around the table for a minute or longer. Your goal is to ask her out for a drink before you get the check, so that she writes her number on the bill.
Approaching is the hardest part of the game. There is nothing natural or easy about walking up to a girl you don't know and talking to her in a way that makes her laugh, builds attraction, and ends with her giving you her phone number.