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Q: Every once in a while, I stop at a particular restaurant on my lunch break. A couple months ago, I met a very attractive waiter there, who served me as much conversation as he did food. We flirted, and every time I return, he continues to flirt even if he's not the one serving me. The problem is that he's never made a move to ask me out, and I think it's because his boss is always keeping a close eye on the employees. I'd like to see him outside the restaurant sometime, but I'm unsure how to go about suggesting this. Can I give him my phone number in front of the boss? Or do I just keep returning in hopes he'll slip me his number eventually? --Katie

Dr. Susan: Waitpersons, like actors, play whatever roles pay better. Waiters and waitresses I've spoken with assure me that when they put on a happy face, they get bigger tips. I'm not claiming that this flirty waiter you have your eye on isn't attracted to you, but if you've seen him quite a few times already and he hasn't made a move to get to know you better, then he's either extraordinarily shy (which isn't likely if he flirts so openly) or he simply wants to keep things at the same level. You might be able to get a conversation going ("Hey, does your girlfriend get discounts here?" ) in order to learn more about his status. There's nothing to keep you from very quietly slipping him your phone number, but don't be surprised if he doesn't act on it. If he's as attractive as you say, he probably gets plenty of attention from customers. The alternative you suggest -- raiding your future retirement funds to eat at that restaurant constantly -- sounds a little desperate. Just don't mistake professional friendliness for genuine romantic interest.