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"Hitting" on the Waitress (server) Is it OK?

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Last weekend, I had a wonderful experience with a lovely little waitress!! She was not overly flirty (like the hot bartender in short shorts), but rather extremely knowledgable about food ( major turn on) Durring the couple hours at this place, came to find out we had ALOT of stuff in common.

Now everyone at the table immediately said, too bad she was our waitress you could of asked her out. They all proclaimed , there is nothign worse than a cusomter hitting on you or trying to ask you out. Needless to say I was really bummed out, but plan on going there next and really want to get some others opinions.

  1. Please, just please, do not ask her out while she is working. While you both may have hit it off and while she may have been interested in you, the fact is, she works in customer service. It is her job to keep customers happy. You were her customer. I would strongly suggest you follow her lead. Plus, there is nothing worse or more awkward than being asked out by a customer, especially when you don't feel the same way. Remember, when she is at work,(and to some extent, even when she is not), she are representing the restaurant, and therefore is not fully able to respond as she might want to. I really think your best bet is to hope to run into her someplace else, and see how she acts towards you, but please, try to be very mindful of creepy stalkerish behavior.

    I know it may sound like I am going overboard, but there is nothing worse than being stuck on the floor with unwanted attention. Even wanted attention is tough. There's no place to hide, and to a large extent, a waiter is acting while working, if that makes any sense. It is very hard and somewhat disconcerting to try and mix business with pleasure.

    1 Reply
    1. re: hilltowner

      Great points, and things that MUST be considered.

      I will follow this thread, as I might learn something about single society, now vs what I once knew.

      Hunt

    2. but there is nothing worse than being stuck on the floor with unwanted attention. Even wanted attention is tough. There's no place to hide, and to a large extent, a waiter is acting while working, if that makes any sense.

      --------------------------------------------------------------------------------------------------------------
      As a former waitress, I agree with the above. The females would get hit on and asked out on dates ALL THE TIME. I wore a wedding ring to work and I wasn't the only female that "lied" to the customers about being married.

      But then again, I married one of my customers nearly 20 years ago :) so sometimes asking out the server pays off. (He was a friend of a friend that I never met before that night and he knew I wasn't married.)

      1. If you run into her outside of work, then by all means ask her out. If not, no. Odds are you will just create an uncomfortable situation for her.

        1. The best thing you can do in the situation:
          Casually probe questions w/o ever being to blunt, just to see her reactions.
          "what do you like to do when you're not working"
          "are you allowed to have a drink"
          "whats your favorite food"
          Take notice to her reactions, body language, how she responds, tone of voice....and go from there.
          But yes, tread lightly, over a period of time...

          1 Reply
          1. re: Glutton4Grub

            No,no, no,no. Don't ask her those "casually probing" questions, you stand a large chance of just appearing creepy. I don't know you, but it really doesn't come across well, at least not in print. At the very least it's obvious what you're trying to do and there you are, possibly creating an awkward place for her while she's stuck at work.

          2. I have had many long and short "flings" with many a waitress. Usually, this happens at places where I am a regular, and we usually only get together after many hours talking and hanging out at their place of establishment and/or their post-work hangout.

            That said, flirting is often the name of the game for workers in the service industry. And customers that shadow the servers and give too much attention are absolutely seen as a nuisance. So never do that. You have to establish a good, honest rapport, or else it ain't going down, and it's extremely difficult to do so when the server is working.

            Asking a server out when they are working is poor form, and unlikely to succeed in any case. You are in a client relationship, and her job is to make you happy. Perception in such situations often doesn't match reality. Unless you are able to run into her on an even playing field, off hours, to truly establish a rapport, then I don't think you should ask her out. You'll probably only end up embarassing her and yourself.

            First problem is, even if you do end up talking with her off hours, you are still a prospective client, and reading intentions will remain difficult. Second problem is, unless you are a regular, you aren't going to have a chance to hang out with her off hours, unless she accepts an ill-advised advance while she is working. It's a paradox.

            Long story short: don't be a creep and ask out a server while they are working.

            All of that said, I love servers. Had one over last night, in fact. Laughed when I came to the ch boards today and this popped up.