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Flirting with a waitress/bartender?


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Posted

I've been frequenting this restaurant/bar recently (from a month ago) where there is a cute waitress. I never thought about asking a waitress out until I met her. Now I need some advice whether it's a good idea or not since they are, after all, paid to chat/flirt with customers.

 

I'm 24, she's around 22. She just finished school. My messed up schedule has me up until the wee hours of the morning. I usually visit around 12-2am (they close around 4am)

 

The first couple of times we had short conversations and that was that. Since this is the one of the only places open and serves decent food, I roughly come by 2-3 times a week.

 

As I became a regular, we had actual conversations lasting more than just a few minutes. We're both Asian (she's Japanese) and we'd talk about where we were from, etc. I got her to talk about her interests and had her tell me about her life/dreams. There are times when she'd come by and continue the conversation but it doesn't happen all the time. The conversations were good and length as I didn't bother making small talk every time she walked by.

 

I did my best not to seem like a creep by only talking to her when I had something to say and not taking up all her time. I'd flirt and she'd flirt back. Sometimes we'd be talking and I'd notice her playing with her necklace. I took it as a good sign and figured I there's at least some bit of interest level.

 

Earlier this week she told me she liked art and visiting museums. I suggested an exhibit that caught her interest and told her she should go. When I told her this, she just look down/away and said "yeah, maybe sometime". Looking back, I couldn't help feel that she was waiting for me to ask her to go. The modest part of me thinks I'm overthinking it.

 

We exchanged names that night and when she couldn't pronounce my name, she grabbed a piece of paper and told me to write it for her. When the check came, I noticed that she put my name there in the middle of two <3 hearts. I thought it was really cute and commented on it. When I got up to leave, she came over and said "What? You're leaving now?" I nodded and she said "see you soon?". I smiled and told her I'd be back later this week.

 

Up until now I've seen her about 6-7 times. There are times when we would look at each other from across the room and maintain eye contact but not strike up a conversation. I don't know if this is good or not but I try my best not to show too much interest. Basically seem really chill and non nonchalant about her. But when we talk I'm fairly nice and sweet to her. No idea if she knows I'm interested but I only talk to her over the other waitresses.

 

What bothers me more is that I can't tell if it's genuine interest or just flirting to get tips... although I pay the same 20% every time. So... is it a good idea or is she just "working"?

 

I thought about asking her next time if she'd like to visit the exhibit I mentioned when she had time. Someone told me to just leave my number when I leave...

Posted
Someone told me to just leave my number when I leave...

 

Do not do that! It is the biggest cop out and waitresses and bartenders get that all the time. Besides there is the possibility that she won't even see it and you will be left to think that she just wasn't interested.

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Posted

What if I call her over before I leave and give her my number then?

 

Should I ask when I'm dining or after I get the check? :confused:

Posted

Instead of just asking for her number first, ask her if she would like to go to that art exhibit you talked to her about.

  • Author
Posted

I thought about that at first... but I feel like it would put her on the spot.

Posted

Whenever there is money involved you can never be sure that something is of genuine interest...it's in her best interest to be nice to you, it's also part of her job.

 

However it's definitely not impossible and IMO mostly based on your own ability to charm or build a rapport with a person to gain/gauge their interest. For a guy who knows what he is doing, he can adapt to any situation, even the awkward and unexpected ones. There are no limits/barriers, but for your average joe...a lot of interest is misread and misunderstood, which can lead to some awkwardness because they get nervous and over-think it instead of just react with confidence and keep it light with easy-transitions.

 

You build it up in your head and create this bubble, with these hints and subtle probes of flirtation and interest while trying to appear casual/relaxed and semi-interested...that's all fine and good for the mysterious trick, but engaging women is about "flow" and opportunity, that doesn't usually happen on your watch..the window so to speak opens and that's when you need the confidence to react at that time and go with it, without being apprehensive or second guessing yourself...that's when you mess up and cost yourself points, then start to slide backwards down the hill trying to regain a footing (this might sound vague to a lot of women but it will make sense for many/most men).

 

Based on your demeanor and hers it is possible that she is interested...but that has to be more carefully pursued at this point because you kind of missed your bus...I personally don't recommend putting your number on a thing or just straight up asking her out on a date...mention the museum again or some other activity she might be interested in, then you could get her number and plan a "date" without being so direct...and if you two get along well enough and there's a spark/chemistry, the rest will take care of itself.

 

Don't build it up in your head as a date or asking her out, just be casual about it and leave her guessing at this point what your interest level is...If there's no other men around in her life or she's feeling a bit lonely and going out on a date with a "friend" from the cafe or "potential date" which she'd surely ask her all-unknowing friends...then she'll go out with you if she's feeling you at all. Otherwise just let it go, because meeting someone 6-7 times and just having it be this casual interaction is not a great sign for me to pursue...maybe for you and some other guys but If I'm interested I don't let things linger, IMO that's a bad way to do things with women for many reasons but also not my personal style...I don't friendzone myself.

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Posted

Great response. Will quite wasting time and attempt to get her number next time.

Posted
I thought about asking her next time if she'd like to visit the exhibit I mentioned when she had time.

 

This, be proactive. Don't leave her your number because she may be the type of girl who's shy about taking the first step of calling/texting or it seems kinda "lazy". I've had attractive guys leaving me numbers and I wouldn't call them because it feels like they're expecting me to do "the work". Just ask her out, all you have to lose if she says no is never going to this restaurant again to avoid the awkwardness.

Posted

Don't do it.

Posted

Go there like any other night you go there. Do the small talk you always do with her. The only difference is, your going to ask her number at the end of the night before you leave.

 

Just ask for her number, and dont utter a single word. Pay attention to how she gives it to you. Once you get it or not, get out. I suggest to not take her to the art exhibition on your first outing. Take her there on the second or third outing (if you get there).

Posted

I bartend. We do that so you'll tip us more.

Posted

The only way your going to find out if she has any interest is by asking. What's the worse that could happen? She say's no? Most guys have been told no a lot of times, it goes with the territory. Who knows, she might say yes. Better hurry though because you might cool your way out of a date with a nice girl. Times A wastin.

Posted
I bartend. We do that so you'll tip us more.

 

For the most part. I had a friend over the weekend tell me a bartender asked him out and she gave him his number.

 

I don't care where you work or what you do, if you really like someone, and there is mutual interest, it will happen if someone steps up and makes the initial move.

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