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Advice Needed on Asking Out A Waitress...


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Coffee Anyone?
Posted

Long time lurker here and wanting some much needed advice. I frequent a neighbourhood restaurant for lunch at least once or twice a week and over the past six months, I've made the acquaintance of a waitress there. Let's call her "Sue".

 

Over the course of frequent visits and conversations, I've discovered that Sue is here on a student visa from Mexico. She speaks very limited english (we usually have trouble communicating beyond hello and how are you today?). But at the same time, we've always made a point of smiling and maintaining eye contact. And we always engage in conversation and she never has less than a big grin for me. I also slide her plenty of winks and grins and try to let her know that I find her appealing.

 

The complication aside from her being a waitress (and yes, I know that waitresses are paid to be friendly and flirt), is that she is a waitress at one of my favourite restaurants! And if she declined me on a simple coffee, I'd probably be too embarassed to return.

 

So, bottom line is, I find her quite attractive and appealing but I'm not sure she's friendly just b/c it's her job and I also am not sure I want to gamble my favourite restaurant against a coffee date.

 

Advice? Suggestions? I might add there is a language barrier as mentioned. She speaks little english and I speak no spanish.

Check Please
Posted

The good news is that you don't have to worry about whether she really likes you or is just working for tips. Because the bad news is that, IMHO, it is *always* bad manners to hit on someone who is professionally obliged to be polite to you - the power differential is just too great. I've had starry eyes for food servers in my time as well, so I feel for you. But hunting this species just isn't sporting. Sorry.

Posted
Originally posted by Coffee Anyone?

So, bottom line is, I find her quite attractive and appealing but I'm not sure she's friendly just b/c it's her job and I also am not sure I want to gamble my favourite restaurant against a coffee date.

 

Advice? Suggestions? I might add there is a language barrier as mentioned. She speaks little english and I speak no spanish.

 

Why do you wish to have coffe with a woman with whom you don't share a language? My instinct is that you simply think she's hot and want to nail her, which is cool, although not discussed too often on this forum (which, after all, isn't "laidshack").

 

My advice - ask her to a party as a friend/group thing and make your move. Do bear in mind two things: if she rejects you at the party, it'll be worse than her rejecting your for coffee in terms of seeing her at the cafe after. Second, if you hit it and forget it, you'll really be embarassed to go back to the cafe.

Posted
Originally posted by Coffee Anyone?

The complication aside from her being a waitress (and yes, I know that waitresses are paid to be friendly and flirt),

 

Advice? Suggestions?

She is being friendly with you to get big tips. Which I am almost sure you are giving her already. You are already in friends/regular customer/big tipper category.

Posted

Never assume anything with people who are paid to be nice to you, unless she gives you stuff for free.

Posted

Scratch raises a good question. I was wondering the same: "Why do you want to go out with someone whom you barely understand?" If you're seriously interested in her, learn some Spanish and then try to ask her out for a coffee anything else is just a waste of time, if you're looking for a serious relationship of course.

 

My guess is though, if you're the kind of guy who worries ahead about going back the the same restaurants if he gets rejected than I can tell you in advance you look like the kind of guy who tend to fall for a smile and a wink from a pretty woman who is only nice to you but nothing else. In this case she even belongs to a group of people who get paid to be nice.

 

I tend to believe that guys who simply fall for pretty women because their pretty don't really get that far. Usually they are trapped in the friends category and sometimes when she needs a shoulder to cry on she will remember you. Those guys never really have enough self-confidence to attract her, not for a relationship, but also not for fast sex (they're simply not assertive enough).

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