Kitchen Posted March 19, 2014 Posted March 19, 2014 My friend and I frequent this tiny hole in the wall restaurant in my town like twice a month. The restaurant has 3 waiters, and two of them (male) are the the owners of the restaurant as well. The 3rd is a female waitress who seems to be my age (early-mid 20s). She is very nice and sweet, and smiles a lot, but then again all waitresses are like that because that is their job. A couple of years ago, when I didn't have much experience with women, I asked her out to dinner, and blew it. This was near the end of the night when my friends and I were the last customers. My friends walked out the door ahead of me, and while she was cleaning my table I asked her if she wants to go to dinner some time. She said "maybe" and since I wasn't expecting that (I was prepared for a yes or no), I just said "ok well I'll see you around here some time". I know, big mistake. I don't know if her maybe meant no or yes or really a maybe or a maybe just because she felt obligated to say since I was a guest. I should have just asked for her # or something. Anyway, I'm at least happy that it was never really awkward after that. We have continued to dine there since then and at some point I just decided on giving up on asking her out, because I was worried about the awkwardness, since we are frequent patrons. We have each others names, she knows what I order, and the condiments I like. She also happens to have a lot of friends of my ethnicity, so I know that she likes my people. I want to try to ask her again, but it's so damn difficult. For one, the restaurant is tiny so it would be hard to ask her while not having anyone else hear. It would also be hard to get her alone. Maybe I can just make conversation with her, but I never know what to say, since I am there always with my friend (so I feel more pressure). Any tips, solutions? I tried to lay out the scenario as best as possible. Thanks for reading.
Gaeta Posted March 19, 2014 Posted March 19, 2014 About you go to that restaurant on your own? Try to go at a very quiet time of the day so you can start a conversation with her without holding the service to other clients. I am thinking she works in a restaurant surrounded by food all day so about finding another kind of date, like a movie, skating, bowling, rock climbing, etc. This is my feeling but maybe she would like a dinner too. So you start up a conversation and make your invitation. Make it clear, a movie Saturday night at 8pm. if she says she is busy and does not offer to reschedule for the following day she is not interested.
Author Kitchen Posted March 19, 2014 Author Posted March 19, 2014 About you go to that restaurant on your own? Try to go at a very quiet time of the day so you can start a conversation with her without holding the service to other clients. I am thinking she works in a restaurant surrounded by food all day so about finding another kind of date, like a movie, skating, bowling, rock climbing, etc. This is my feeling but maybe she would like a dinner too. So you start up a conversation and make your invitation. Make it clear, a movie Saturday night at 8pm. if she says she is busy and does not offer to reschedule for the following day she is not interested. Isn't it weird though if I show up to this restaurant alone, and get a table by myself? And the other waiters might be there too so it's not like I'll totally be alone. I'm thinking that it might just be easier to ask her out at my table at the end of my meal even though it may be in front of my friend. Less creepy then being there alone? And another thing, do I ask her out in the first conversation I start up with her? Or do I have to build something up over several conversations?
germain Posted March 20, 2014 Posted March 20, 2014 I'd say ideally, you'd get a good conversation going (as much as you can in a busy restaurant), have her laughing a bit, flirting a bit, and then throw out a "you should come...with me". If she says yes or maybe, "well let me get your number, and I'll give you a call." If there's no resistance, you're good to give that a shot. If she doesn't return the call, then it's not likely to happen. But I'd only shoot out one call if you want to continue to frequent the restaurant without it getting awkward. She can always say she missed the one call and you just brush it off saying it's no big deal, and you guys drop it. That said I think it's hard to pick up a girl where she works. She's probably getting hit on a lot, and she's probably in business mode, thinking about paying her bills. Unless a waitress or bartender is especially flirty or giving me more attention than anyone else/touching me, basically really obvious signs, I don't bother. I'll flirt back and maybe jokingly ask her out, but I haven't really expected much from those encounters. 1
Trimmer Posted March 20, 2014 Posted March 20, 2014 Man, your last overture was a couple years ago? This is definitely a slow build up...
Ajax Posted March 20, 2014 Posted March 20, 2014 My friends walked out the door ahead of me, and while she was cleaning my table I asked her if she wants to go to dinner some time. She said "maybe" and since I wasn't expecting that (I was prepared for a yes or no), I just said "ok well I'll see you around here some time". I'm by no means an expert on asking women out, but I think I'm generally pretty astute at gauging social interactions, and I think you're barking up the wrong tree. It sounds like you really did catch her off guard, and if she fancied you I think she would have been a little more prepared with a positive response. I also think if she was interested in a date with you she would have made some sort of overture herself to follow up in the course of the past two years, like leaving her number for you on a check or receipt, or giving you a little more attention than other patrons. I think you'd be doing yourself a favor to let this one go before you have to find a new place to eat. 3
Author Kitchen Posted March 23, 2014 Author Posted March 23, 2014 Thanks for all of your replies. I'm by no means an expert on asking women out, but I think I'm generally pretty astute at gauging social interactions, and I think you're barking up the wrong tree. It sounds like you really did catch her off guard, and if she fancied you I think she would have been a little more prepared with a positive response. I also think if she was interested in a date with you she would have made some sort of overture herself to follow up in the course of the past two years, like leaving her number for you on a check or receipt, or giving you a little more attention than other patrons. I think you'd be doing yourself a favor to let this one go before you have to find a new place to eat. I see what you're saying. In general, I notice she is very friendly, always smiling/laughing with me. And she also knows some words in the language of my ethnic background, that she spits out sometimes (remember I said she has a lot of friends of my race). In fact she said "goodbye" to me in my language after I asked her out that day. But perhaps you're right and she was just trying to lessen the tension after I asked her out. Now I don't know if she's really nice/smiling with me because she is a waitress, and that's her job, but she def. smiles more than any other waitress at other restaurants. Another thing is that, you all probably assume she gets hit on all the time...since she is a waitress. But the thing is that this restaurant is mostly frequented by old people. I'm not kidding when I say this, but 9.5/10 times we go there, every other patron in the restaurant is in their 50s or 60s, or if they are young, they happen to be couples. I have never seen young single men there, ever. Besides us. So she definitely doesn't get hit on most of the time there. But sigh..this is such a tough situation. I guess I'll try to say what germain suggested and pretty much just get the ball rolling by conversation. No other easy way. Any other opinions? Thanks again.
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