How can I ask a waitress on a date?
It is important to know what you are dealing with in trying to ask a waitress out. There are two main ways to go about it, and your choice will depend largely on whether you are making a one-off visit to the bistro in question or plan to make it your local.
But first, a little bit about the general attitudes and working conditions of your waitress.
Most restaurants hire young, unmarried, attractive waitresses because they tend to be the kinds of girls that go in for waitressing jobs. It is not an easy job. Shifts can run from 8 to 12 hours, and the girls spend that time entirely on their feet. Waitresses are not paid a full wage. They are expected to make up for this shortage with tips. They are friendly, helpful, courteous, and outgoing because they want a big tip. Your waitress may even flirt with you if she thinks you’re hot. But you should not misread the situation: she is not sending you the signal to ask her out; she is merely working for a tip.
The cold approach to asking a waitress out is the one that is most fraught with peril. Think about it. From her point of view, you are a complete stranger trying to get into her panties while she is busy trying to make a buck. Things may turn out in your favor. She may be single, on the rebound, and looking for some action; it may be a slow night, which gives her plenty of time to chat and be chatted up; you may be able to stay at the table long enough to develop a nice rapport with her and speak to her when her colleagues are nowhere in sight. Such a succession of events is possible, but highly unlikely. In any case, going for a cold pickup leaves too much to chance. Even if she does like you, is not busy, and is not under the gaze of her fellow servers she will probably still rebuff your advances.
Waitresses, especially the attractive ones, get hit on all the time. On any given shift, your waitress probably gets a dozen or more guys, just like you, who try to make moves on her. Most waitresses maintain a strict policy of not getting personal or too intimate with customers. Why does she flirt? Partly to get a tip; partly to entertain herself. Serving people food and drink all day is not among the most exciting activities in the world. If a waitress has a hot guy as a customer, she will of course take the opportunity to get some pleasure out of her interaction with him. This doesn’t mean she wants to take things any further.
If you want to ask a waitress out, the safest route is to make yourself a regular customer. The restaurant may be out of your way. There is nothing to be done about this. If you must have her, then you must do what is necessary to get her.
But let’s pause for a moment. This is an unwise and wasteful course to take if you have received not a single sign, indication, or vibe that she is interested. A long stare, the breaking of the touch barrier, an unguarded moment in which she tells you something personal—these are indications that she’s into you or has the potential to be.
So let’s say that everything seems right for the longer, more gradual strategy of asking a waitress out. How and when is it to be done?
You should start plotting the big moment after you have been identified by her and her colleagues as a regular. You need to get your waitress to see you as a person, as being more than part of her job. The usual small talk about your work and interests applies, but you should also steer the conversation towards relationships and dating; doing so will lead you to the facts about her relationship status.
The actual act of asking her out can be tricky. She will want to protect her reputation among her colleagues. Allowing herself to be picked up by a customer can make things awkward for her at work. But your waitress is not a machine; she can’t switch off her feelings and her emotions and her pussy when she clocks into work. If she likes you, then she will respond to your wooing. Your main aim should be to make it easy for her to say yes, which is best done by being discrete.
If you have become a regular customer, you have gotten a sense of her routine. Catch her at a moment when she is not particularly busy or when she has stepped out for a break or when she has made the time to linger at your table longer than usual. Propose something simple. Asking her for coffee at a bookstore is a good one, especially if she is a student.
Another way of going about it is asking her if it’s okay to Friend her on Facebook, and mentioning your desire to send her a message about meeting up some place in the future. This last bit must be added, as friending someone on Facebook means nothing. You must state your specific intent to use it as a means of communicating with her about personal matters outside of her work.
The bottom line is if you’ve seen a hot waitress, go for it. With the right strategy you will avoid rejection, embarrassment, and time wastage.
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About Christopher Reid Chris was born in Washington, D.C. and lives in Britain. He works as a blogger, essayist, and novelist. His first book, Tea with Maureen, has just been published.