Ask her what she’s doing for lunch that day. If she tells you what their lunch specials are and goes farther back into the establishment, follow her, and say “I was asking what you were doing for lunch. Would you like to have lunch with me?”
I don’t agree with the people saying you shouldn’t do it because it might make them uncomfortable and they have “no escape”. I’ve experienced flirting that made me mildly uncomfortable (from men as well as women… I am a straight man) in a work environment, and also in a social environment. In either case I didn’t want to be rude and was able to blow them off gently. So in other words there is a certain amount of social pressure to be polite to people whether you’re being paid to be polite or not (assuming they aren’t being outright rude themselves, that’s where it really differs IMO) and unwanted advances can make anyone uncomfortable regardless of the setting. But being at work doesn’t make them any more compelled to say yes than if they weren’t. It’s not like their manager is going to chastise them for not going on a date with a customer.
So if you really want to do it do it how you’d ask anyone out - be confident and straightforward but if you get rejected then suck it up and move on. Although if you are asking out your server at a restaurant then wait until you are getting ready to leave because otherwise things could get awkward. 
First, let me add to the chorus of “don’t touch him/her.” Maybe especially her. It might seem mild and friendly to you, but it’s way too easy to cross the boundary between friendly and creepy. Really.
Second, understand that some companies have strenuous rules about fraternizing with clients. The first hotel where I ever worked had a very, very strict rule against that. As an employee, I couldn’t date a hotel client. Period. That was grounds for immediate firing. Mind you, not all companies have rules that strict, but some do, so even asking out a customer service person might be awkward, or s/he might tell you that it’s against the rules, and that s/he can’t afford to risk a job over a potential date with you. It’s nothing personal.
Third, please remember that many CS personnel really are only friendly toward you in a job context. IRL, when s/he’s not on the time clock, she might not be so friendly toward you. Don’t mistake professionalism for friendship or attraction.
If you’ve heard all of these caveats, and still want to ask someone out, something brief and immediate might be in order: “If you’re free for your lunch break, would you join me for a sandwich at XYZ (nearby) location?” Or “You look like you’re having a tough day. Can I buy you a drink/cup of coffee after work? Name the time and place, and I’ll meet you there.”
What does she need to do, make a sign?
You could find out from her co-workers where she shops, hangs out, goes to eat, goes to bowl/golf/whatever, where she lives, and then plot and connive to run into her in a non-work setting where she’s not so unfortunately burdened by societal dictums of having to deal with customers as possible suitors. You’d just be a guy on the street.
However if you actually do all of that freaky stuff in order to run into her, well, then, I don’t want to know about it.
I would say there are a few general rules:
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Don’t bother them while they are busy or otherwise interfere with their job.
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Don’t corner them. Physically or otherwise.
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Strike up a short, harmless converation with them to build some comfort. I would say you want to get to a point where she recognizes you and are on a first name “hi” basis, but not as someone she personally deals with as a customer.
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You might not want to ask out someone at the place you frequent every week.
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Very important - avoid engaging in any sort of financial transaction with them. Whether they are a bartender, waitress, counter girl, or even a stripper, as soon as you start entering into a financial transaction with them you create a conflict of interest that will potentially violate the customer/vendor relationship they have been trying to establish.
So IOW, you want to engage with her outside of customer/vendor relationship. If she’s a bartender, you are there to eat at the restaurant. A waitress, you are there for a drink at the bar. etc.
- Don’t take her out to eat at the restaurant where she works. This should seem obvious.
Really it’s like anyone else. You strike up a conversation, flirt a bit, develop a rapport and then ask her if she wants to meet up at a later time.
Do you realize how creepy your comment is? You seem to be saying that it’s okay to corner someone and harass them because they did not answer repeated calls. If someone isn’t answering your calls, they’re either busy or do not want to talk to you. The person ignoring the calls isn’t the one committing a “faux pas” in this situation, it’s the clueless person who thinks it’s okay to invade someone else’s workplace and personal space to get answers they feel entitled to, but are not.
What the fuck.
Thanks for the input. Although I wonder, what if you don’t really have a reason to be there except for engaging in a transaction or asking them out? To be specific, I’m thinking of an optometrist’s saleswoman.
I don’t see how I could be on a first name basis or engage with her outside the customer/vendor relationship.
In your examples, how would you ask out a waitress? If you’re in the bar/restaurant, it’s likely to be as a patron.
There must be some obvious way I’m missing.
Is asking tem out after the financial transaction is over ok or still off limits?
Well on the flip side it can be very frustrating that almost all women feel avoiding someone or standing them up is the best course of action when they decide they don’t want to date someone instead of doing the respectful thing and simply saying so.
I’m a guy, so I sympathize with you, however it’s bullshit behavior like what **SeaDragonTattoo **had to endure that causes so many women to do just that.
I think it’s also important to do the asking-out at the very end of the transaction, when you’re about to head out the door. This saves a lot of discomfort for both people, especially if the offer is rejected.
At the moment the transaction is coming to an end (you’re getting your change, or receipt, or your item is being put in a bag) just say “You seem really nice, could I call you sometime?”
If she says “yes,” don’t immediately whip out your cell phone or grab for a pen—maybe she doesn’t want the manager, co-workers or other customers to see. Give her a second to make the first move—she might discreetly write it on your receipt. If she starts to verbally tell you the number or just stands there, then it’s time to get your phone out.
If she says “no” (which may or may not be followed up with a reason as to why not) just be graceful about it. Don’t make a big ceremony. Just accept her refusal, wish her a good day, and leave. If you do it this way, you shouldn’t have to be uncomfortable or embarrassed (and neither will she) when you go back for future purchases.
Also, if the rejection comes with a reason (it’s against the rules, I have a boyfriend/girlfriend, I’m moving out of town, et cetera) it’s probably best to not question it. It’s likely to be a white lie and if you try to find out the real reason you got rejected you’ll make the other person very uncomfortable and yourself very sad.
And again, I do stress, make all your purchasing decisions without regard to this person’s attractiveness, and proposition them at the end. If you do so at the beginning, they’ll feel a lot of pressure to treat you the way you want to make the sale, or avoid a scene. Not cool to do that to people.
Also, the reason I suggest just asking for the person’s phone number is because you want to make the whole thing quick and inconspicuous— this person is working after all. You have no idea what kind of relationship they have with their co-workers, management, or anything. If a few gossipy colleagues start hearing stuff like “Well, which movie would you like to see with me tonight?” that won’t be good.
Hmm, interesting. Is it a standalone optometrist or in a mall or shopping plaza?
Regardless, you need some type of pretense to be in there in the first place. If you go in there with “I was walking around the food court with my baseball cap and reversible jacket taking advantage of the free samples, and then I went back out to the car for my other jacket and I saw you on your cigarette break and damn you’re hot! So I checked out your name tag and followed you in here.” Well, that wouldn’t go over very well.
Anyway, do you wear glasses or contacts? Did you buy glasses there? If your glasses don’t fit well, most optometrists adjust them for free, even if you purchased elsewhere.
If it’s in the mall, maybe you could go during a slow period and just sort of wander in and act as if you’re bored and killing time so you’re looking around in pretty much any store that looks interesting. “They’re replacing my car tires in Sears and it’s taking forever!”
Any children or elderly people in your family who need help getting glasses? Bring them there! A curious and cute (but well-behaved) kid could put everyone in a good mood and be a conversation starter.
Is there anything at all about this woman’s appearance or dress that you can use as a conversation starter? “Oh, I saw your name tag, you’re not related to the Joneses from Milwaukee, are you?”
Anyway, just find some kind of pretense to get yourself in there long enough to chat with her and charm her with your wonderful personality and make her laugh. When it’s time to leave, tell her you liked chatting with her and ask her if you can call her sometime.
Wow. When I was working as a bank teller, I had a customer who was convinced I looked just like his ex-girlfriend. He kept telling me how beautiful I am, etc. He asked me out on a date, but I was engaged at the time. I politely told him that I was flattered, but engaged to a great guy. He seemed to shrug it off, but next week when he came in with his paycheck, he insisted on waiting for me to help him. I did, as was expected of me as a service professional. He told me I should leave my fiance for him, that he could take care of me better than my fiance could (he didn’t know my fiance, what he does for a living, nothing) and pointed at his paycheck (which wasn’t that much, to be honest). I politely said that I’m very in love with my fiance, but flattered. He nodded, I finished, and he left.
But he kept coming to my window, week after week. Each week, getting a little closer to scary. Touching me, asking when I’m done, etc. But since I was paid to be nice, I kept being nice, deflecting, reminding him I’m engaged.
After 5 or 6 weeks, it was really getting creepy. He was said something like, “I’ll take care of you. Get you a nicer house than that old blue one you’re living in.” I was shocked. In the silence, he admitted he knew which street I lived on and that “we’re practically neighbors” (he lived about a mile from me, from the address in the account).
I spoke to my boss, told her what was going on. She said I should suck it up because I “must have been leading him on.” I was like, WHAT?!!?
I wet to HR because that didn’t seem kosher. They consulted the legal team and they said I didn’t have the case for a restraining order because he never threatened me (and some more reasons). But HR did say that I should get other tellers to help him. They told my boss to vary my schedule on Fridays, so it’s harder for him to stalk me. They said that the other tellers should insist on helping him immediately instead of having him wait. And so on and so on.
Moral of the story: just because someone is paid to be nice doesn’t mean you can touch them, insist upon them, force yourself upon them. Don’t. As someone who has been on the other side of that equation, it’s beyond “uncomfortable;” it’s frustrating, difficult and very frightening.
It’s in a mall. I walked in there yesterday to give out my resume. I was told the process is centralised and to send it through a website.
I am indeed four eyed and I used to have glasses from a nearby shop of the same chain.
I took this as an example although I realise optometry is not the way I’ll meet most of my dates.
Waiting until the end of the transaction, quietly asking for lunch and exiting without fuss is what I did the last time I asked a saleswoman out (also an optometrist, for some reason).
I actually follow Vinyl Turnip’s suggestion, even though he doesn’t mean it.
All I can think is how much I wouldn’t want this to happen in front of my co-workers. Make sure you’re discreet enough that any other employee in the store doesn’t know what’s going on.
She didn’t describe the date – perhaps there was a reason she wasn’t returning his calls.
Well, he spent most of dinner trying to sell life insurance to the waitress.
Does that help?
It sounds like he should have started a thread named “How do you perform customer service duties when you are out on a date?”
**BigT **has some… *unique *ideas on social interaction. They basically amount to “never say or do anything that could ever cause anyone else to ever feel that they’ve done anything bad, even if they are doing something bad, because then you’re just as bad as they are.”