Went to a Yelp event with a couple of my female friends. (Apparently Yelp has events!) It was at this new distillery/bar. Anyways we talked with the bartender a bit but I didn't really make any moves.

The upside here is I was hanging out with two attractive women so should have some good pre-selection. They're also really outgoing so we ended up chatting with her for a while, and a couple times she told us what days she worked and that Monday's she's there by herself. Not that this was addressed to me, it was more to the group... which, honestly there's a tiny chance she's a lesbian because my friends are and maybe they were hitting it off.

Anyway, I didn't really make any move that night but I'm toying with the idea of going back by myself on Monday.

If so what do I say? One option is to joke about her making the right drink, since she didn't have the ingredients for the first drink I ordered so she gave me something else.

Another option is, if she recognizes me and says something like "hey it's you again!" I could respond with "don't get too excited I'm not sleeping with you."

Although that might be out of character for me...

So other ideas? Or is this just an entirely bad plan and I should have tried for her number right away the first time?

There's a very good chance she won't remember the drink pouring incident, remember she pours hundreds of drinks every day.
No.

Why not just roll back in there with a friend or alone and banter with her, see if there is a good vibe, and then get her #.

Well, that's what I was trying for...

You're probably right about the drink, the only reason I'd think she might remember is that I playfully gave her a hard time about it.

Bartenders are my specialty. The hot ones are considered "celebrities" in under 100k towns, and they act like it.

They see a ton of game, and have way more opportunities to hook up than office workers. Attractive people are attracted to attractive people, etc.

Go back in alone a week later and tease her a bit. Look for good solid eye contact when she's *not* talking to you. Bartenders are very good at checking you out when you think they aren't (behind a stack of glasses, peering around the center bar, using mirrors, etc)/ If you see her doing this, you've got a good shot.

Be cocky and playful, and go right for what you want. Don't dither. Your playfullness a cockiness takes her out of manipulation mode.

Typically, hot bartenders are alpha bitches who play games. It's a job that requires solid manipulation skills. Keep your frame.

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Great advice not just for this situation, but every situation.

Ok first off thanks for the advice everyone!

Things didn't quite go as planned, in that the bar was "busy" rather than quiet due to a sportsball event nearby. Almost didn't find parking and then almost used that as an excuse to chicken out but I decided not to be stupid.

So she remembered me and chatted with me for a few minutes when I first got there, so that was nice. I thought I caught her looking at me a couple times but not really sure, and at least once it turned out she was looking outside at people coming in. Most of the time though she was doing "bar things."

She did come over and chat briefly a couple more times, which led to me telling her about the company I'm starting. Hopefully that played well.

Halfway through my second drink a couple came in and the girl looked kind of familiar, who it turned out was a bartender at another bar I used to frequent years ago. So we ended up talking, and of course the target ended up talking shop with them and I ended up with a free drink out of it. So... more social proof? Or does she just think I'm a lush now...?

Now maybe the best sign is that she asked me twice, as I was leaving, if she'd see me again. I just replied "Probably."

So, I don't really know if she's interested and I know you guys can't answer that... but should I go back again next week? Or wait a couple weeks? Or I'd say this week but I don't think I have time...

Good job man but remember you can only play it cool for so long. You could have played it playful with her when she said "will I see you again" and segued that in to a future meetup one on one. Don't sweat it. But she seems interested from what I can tell. Next time try to close for a future one on one meeting.

Yeah, I realized that last night when I got home from work. I hope some day to think of the right thing to say less than 24 hours later!
OK cool, guess I'm going back Monday. Thanks again!

The ongoing saga...

I maybe shouldn't have gone tonight, since I only got three hours sleep last night. Might not have mattered though.

Got there, ordered a drink, we talked a bit about her day, she was tired from getting up early, getting to work early and working on setting up her art gallery. So maybe she was just tired... but basically after that she only came over once or twice to check if I wanted food or another drink. For the first 10-15 minutes she spent her time cleaning glasses and such, then the bar started to get crowded (it's a small bar so it was really only like 10 people) so she was busy with customers at that point.

I mostly spent the time on my phone since the TV's weren't on and I didn't want to just accidentally be staring at her the whole time. Maybe that was a mistake?

I start getting my stuff ready to leave and she turns around to say goodbye, I tell her

Me: "If I don't see you again have a great Christmas and new year!"
Her: "Wait, why wouldn't I see you again?"
Me: "I'm starting an acting class next Monday and not sure I'll have time."
Her: "Oh, ok... well you know where to find me."
Me: "Do I really? "

I mean, if we'd been chatting the whole time I probably would have said we should meet up right then. Maybe I should have anyway?

As it is, I'm thinking maybe go back in a couple weeks. I'll be on vacation so I could go in early before my class... but basically I'm a little confused, she all but ignored me when I was there then acts like she's disappointed she might not see me for a while?

At this point I would stop by for a quick drink next time and just ask her to meet up. Learn from this one for future endeavors: Strike while the iron's hot.

Should I wait the two weeks then? Or try to stop by on a different night (difficulty: Monday is the only night I remember that she works and my schedule actually is crazy lately.)

Couple other things to remember: it's their job to make you feel wanted and to banter flirtatiously with the customer. If this is a bar you regularly attend be prepared for weirdness to ensue if you see this girl and things don't work out. I might pop in with a friend some night and if she's there, banter for a minute and invite her to meet.

It's not a place I'd go all that often, so no worries there. My current plan is to go Thursday between my company's holiday party and a meeting with my startup partners and just say something like: "I've only got a few minutes but I wanted to say hi. I was thinking I like talking to you, but my schedule's too crazy to keep coming here. We should make plans to meet up."

Or something to that effect anyway... worst case scenario I know to move on.

I get that you're trying not to be rejected and that's why you are holding off pushing it to the next level. Why not try bringing in a female companion with you one day? Bring in one that may be interested in you in order to create tension in the bartender. If she is really interested she's going to start acting busier, avoid eye contact when you look towards her, and probably be one wording you when you order a drink from her.

Then go in another day alone and see if she asks about who you were with. If she asks, that's your opening to reel her in by saying that you're just seeing where things go with the other girl.

If you can demonstrate that another woman wants you, it will open up other women's eyes. If the other woman was already attracted, she will likely become more open and proactive.

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Number Closed!

Thanks for all the help guys!


Basically just walked in and told her I'd been coming in hoping to get to know her better, but she's always busy so I thought I should just ask her out.