Generic rules if you're going to try to ask a cute waitress out:

  • Remember that she's getting paid to be nice to customers. Remember also that she might be unusually nice, or even flirtatious, with customers in an effort to increase her gratuity. Watch what she does with other customers (both male and female), and compare. If she's the same or almost the same with everyone, then it's either her normal personality, or she's playing the part.
  • If she does seem to like you, at least try to get on good enough terms that if and when you do ask her out she is comfortable with you. You probably don't want to walk in, see the waitress, and immediately ask her out.
  • If you ask her out, do it in a public place (the resturaunt is fine), and try to schedule the date for a public place. You wouldn't believe the freaks that these girls run into, mainly those people who don't understand the first rule. Even if she hasn't run into that kind of person, the perception might exist anyway, which would cause her to be overly paranoid.
  • Try to vamp her just a little bit before asking her out. For example, you might want to bring her boyfriend up in casual, random conversation one day. If it turns out that she doesn't have one, wait a few days then ask her out. If you did it right, she took the original question/whatever as random meaningless conversation and might not even remember.
  • I'd suggest against giving her obscenely large gratuities/tips. Give her a normal one, maybe slightly over. You don't want her to think that you were trying to buy her, or that you think that by giving her large tips she owes you something. (A recent real life reference is a British doctor(?) who went to some strip club in New England, ran into a waitress who was working her way through college, and cut her a check for $10,000 to pay for the remainder of her schooling...then asked her out. She declined.)
  • Unless you're God's gift to women, you probably don't want to ask her out in a situation where she feels compelled to answer one way or the other, such as in front of a horde of coworkers.
  • Respect the cute waitress. From what I've seen, they don't get a lot of it from most people. (This is a regional thing, I'm sure.)
  • And finally, remember that, particularly if said waitress is in her late teens or early twenties, she's probably trying to work her way through school. This goes back to the point above.
  • If it's at a place like Hooters, you might not want to bother. From speaking with a couple female friends I know who work in that chain of sex-oriented resturaunts, I can tell you that most of the girls there hate their jobs, can't hold a whole lot of respect for the people who go there, but love the money. The money is why they're there. ($150 for a 6 hour shift, for example.)
  • Speaking from experience I can tell you the following things about dating waitresses.

    1) Never be in awe. Especially of young waitresses. They don't usually consider their job to be glamorous and they laugh at anyone who thinks they are a higher form of life. Tip well, and don't count percentages. Don't make a big deal of it. If the bill is $10 and you have a twenty, say "keep it." Rounding up is the rule of thumb. Cheap is when you do a credit card order and there are cents in the final tally. Never tip below 20%. And tip her co-workers as well as you tip her. Don't be preferential.

    2) Never ask a waitress out. Instead, establish rapport and become a known quantity. This means becoming a regular at the establishment. This only works in bar & grill or coffee houses. Never try this at Hooters or anyplace similar. They consider regulars to be morons unless you can pull off being the intelligent normal member of a group (degree of difficulty very high). Never try this at Dennys or a family restaurant. What kind of person hangs out alone frequently at Dennys? Most waitresses have small bank accounts and live on tip money which means they live a cash based lifestyle. If they are lucky, their salary is enough to pay the rent. A large percentage of single waitresses that don't work until a late close go out somewhere to drink after they get off work. Become a known quantity through gradual stages until you get the invite to go out with her and her friends after work. Don't ask, wait until they bring it up.

    3) You are first just another customer. Then you are a regular customer. Then you are a well liked regular customer. Then you are someone that she and others are happy to see when you arrive. Then you are a friend, like one of her co-workers. That is when the invitation gets extended.

    4) Be normal yet interesting. Waitresses hate geeks, loudmouths and demanding jerks. Be entertaining and above all be interested. Following this code requires you be interested in what she has to say when she starts talking to you. Until she starts talking to you, keep your conversational attempts to "hi" and "how's your night going?" and "place sure is busy tonight." If she responds well to your polite greetings, throw in something with a twist. If she is really busy ask "have you been in the weeds all night?" That means something to waitresses, or at least it does in my experience. It is a question of relating to her job stress as a way of reaching a level of understanding. If you notice she is very busy, become her most patient customer, and therefore a sigh of relief when she comes your way.

    5) If you pay attention and listen to conversations between the waitress and her co-workers (try sitting at the end of the bar by the waitress stand for best input) you will learn her dating status. If you are real attentive you'll pick up tidbits about her likes and dislikes in a guy. You'll also learn more than you think while sitting quietly watching the television and sipping your beer.

    6) This is an investment of time. It goes against waitress code to date customers. You need to spend time becoming more than just a customer to get her attention. Most cute waitresses believe, usually as a result of experience, guys come in and look at them and want to fuck them. They don't have to take the risk of an unknown quantity in the form of a customer at their workplace for that. They regularly encounter groups of guys that make comments that are way over the line as far as sexual innuendo and usually try to shake it off with a smile. Any waitress that appears very willing to go home with a customer... look out, because she's probably carrying more than a just that tray of beer.

    7) Let things take a natural course. "Would you like to go out to dinner sometime?" is bad. It puts her on the spot and becomes a "yes" or "no" dating question. "Hey, there is this new place over on Undertaker Avenue that opened up. Want to go some time?" is the more advantageous avenue. If she isn't interested, there are always other events. It is best to bring it up while out with her and her friends at the end of the evening, or maybe after you offer to walk her out to her car. Someone needs to protect the wad of cash in her pocket.

    8) Don't call her a waitress. Don't call her cute. Political correctness has made this a faux pas and she may take it the wrong way. She is a server and she has a name. In the end you'll see she is just another human being, even if her job fulfills some kind of fetish of yours.

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