Posts Tagged ‘date with a waitress


a date with a waitress

Reader N.A. writes:

Is it possible to score a date with a waitress? They seem impenetrable, since they’re constantly flirted with (especially a cocktail waitress) all day long.

Dear N.A.:

While I think it’s possible to score a date with a waitress, I don’t necessarily think it’s a good idea to try to score one. Especially cocktail waitresses. And bartenders.

Coffee and dessert

"Yes, I'd love coffee, and dessert, and a date with you." Image: Daniel St.Pierre /

By now you all know how I feel about dating people at work (i.e. DON’T DO IT). The same goes for trying to date people who are working, particularly in the service industry. What I mean is, don’t try and pick someone up while they’re at work, even if you’re not working with them. It’s not fair. It’s a waitress’s job to be nice to you, and to give you stuff you want. Asking her out on a date while she’s working is awkward and could, from some perspectives, be considered sexual harassment, depending on how far you go with it. It’s not like shooting fish in a barrel, although there are several people who seem to think it is.

This is especially true at strip clubs, where sex appears to be on the menu. You have to remember that this is not the case. Strippers are paid to act like they are sexually interested in you. About 98% of the time, they’re not. Do not assume you are a lucky member of the 2%. Your best bet is to let the women do their jobs without harassing them. Would you harass a secretary, or a nurse, or a librarian? (Please tell me no.)

I’m not saying that it’s impossible to pick a girl up when she’s waiting tables or tending bar (or putting away books or answering phones or drawing blood). You’re just setting yourself up for getting into a lot of trouble or making things really terrible for her if you try too hard.

If you do see the girl of your dreams holding the tray before you or standing behind the bar and you can’t stop yourself, here are my tips for your best chance:

Wait until after she’s done being your server. Write your name, number, and a “I think we could hit it off” on a piece of paper (or on your business card) and leave it with the check. Or put up a post on Craigslist missed connections or in your local newspaper’s “I Saw You” section. If you’re feeling very brave, you could try and find her on Facebook and send her a message, but make sure you don’t just send her a random friend request. You don’t want to be a stalker. And do not, for any reason, say something while she’s putting your drinks on the table or taking your order or interacting with you as a server. That’s what makes it awkward.

Don’t over-tip and hope it’ll make her like you. That just screams “I use money to get what I want and I expect it’ll always work”, and no (or at least very few) girls want to feel that they’re the object of your moneyed affections.

Don’t go back to the restaurant or bar over and over, especially if she doesn’t respond. Sure, it’s nice to have regulars. But having a stalker is not cool. If you’ve asked her on a date in her off-time, be very tactful about going back to the restaurant when she’s working. Try not to sit in her section. Be casual about it, and take rejection well, but do not harry her about it or make her feel more uncomfortable than she probably already does.

Remember that if this is your regular joint, you are going to make things extra awkward for everyone if a) she says no, or b) you do date but it doesn’t end well. It’s a thin line to tread. Just be aware that you may have to quit going to your bar for a while if the relationship goes sour, or if she’s really offended that you hit on her. If it’s at a strip club, you could be kicked out or barred from coming back. Choose your battles, amigo.

I will admit fully that it is far easier for a girl to pick up a male bartender or server than it is for a guy to do so with a working woman. It’s not fair, maybe, but it’s just how sexual politics works out. Still, I think women should take this advice to heart just as much as men should, because men can be made uncomfortable by unwanted advances, too.

Finally: You’re right – we girls tend to get hit on all the time, especially when we’re working a casual job like waitress, barista, or bartender where we have to be friendly, sweet, charming, and cute. You are wise to be aware that you’re probably not going to be the first man to proposition her while on the job. And that can totally wreck any chance you could possibly have. But you can be classy about it, and not put her on the spot. Or you can look elsewhere for your romantic endeavors.

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