Dear Cary,
Here is the deal: I go to this diner on the way to work most mornings, where a really sweet and good-looking waitress works. We talk a little, and I think there might be chemistry between us. Here is the thing -- although I believe she probably is a genuinely sweet person, she is a waitress and makes tips by being nice to customers. So, is there any way to know if she may be interested? And if so, is it inappropriate to ask her out while she is on the job? And is there a discreet way of doing it without putting her on the spot (in front of other customers)? I know this seems a little immature, but I really want to ask her out but I am terrified for these reasons!
Diner Boy
Dear Diner Boy,
Well, you have to ask her out. My wife says you should just invite her out for coffee sometime. That's the universal non-date date. Even if she agrees to that, she's not agreeing to too much.
I mean, you might be tempted to leave her a note, or call her at work, but that might strike her as slightly fishy and annoying and complicated. I think she'll be much more impressed if you just ask her out directly, in person. Because asking a woman out demonstrates that you don't mind showing your attraction to her in public.
The alternatives, though well-intentioned, reek of self-consciousness and they imply certain things you don't want to imply. If you claim you don't want to embarrass her at work, for instance, it might show that you don't think she can handle a slightly awkward situation in public, which might be a little insulting, as waitresses handle awkward situations in public all day long. And if you let on that you think her kindness toward you might be only professional, that, too, could be insulting if she really does care for you. It's like saying that you suspect she's shallow or duplicitous. The best thing by far is to simply ask her out, but with some care and some confidence. Not when her boss is standing there. Not when all the customers can overhear you. If your regular seat is in too public a spot, find a spot that's less crowded. And wait for your chance.
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Want more advice from Cary? Read yesterday's column.
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