I thought I'd throw this one out to the sub to see what you guys would do in this situation.
I've been frequenting a new, tiny, close-knit bar. I've taken up pool and motorcycle riding and meeting some really cool people in the process. There are tons of regulars in this bar (a la Cheers) and I've developed a rapport with many people, including the staff; which was my main goal since I don't really have a home base to just hang out.
All the bartenders are 7's, 8's, and 9's in the looks department, but I haven't bothered trying to get with any of them because they aren't my type. Tonight a new 10 was working. I mean my dream girl, 100%. I now have a new goal: get with this girl.
So the night goes like this:
I ride up and park my bike. I walk in and I don't even make it though the door before dudes start asking me if I'm a motorcyclist and showing off pictures of their bikes in some sort of dick measuring contest; of course I'm the only one riding because it's cold outside. They're talking my ear off while I desperately try to break conversation and ease my way over to the bar. The 10 bartender makes long eye contact and sees I'm trying to break away, so she butts in and says "If I were a beer, what type would you want me to be?"
I excuse myself from the conversation and finally get my beer, and while she's still holding eye contact I say "If I was a cute bartender, what would my name be?". She smiles, we make introductions, she smiles again, and I go challenge some people to pool. Meanwhile I keep catching her looking my way every few minutes.
It becomes clear that most of these people hanging out are the 10's friends in real life. A whole bar full of alpha male types acting pretty drunk and beta. Eventually one of the other bartenders comes in (her night off), so I take a break from the games and flirt with her at the bar for a few minutes. The 10 sees this and begins vying for attention in various ways, so I focus 100% on her and flirt for about 5 minutes. A few minutes later she sets another beer down in front of me and I say "no, I'd better not" and I ask her to close my tab. The whole night lasted about an hour and fifteen minutes.
So here we are, surrounded by her friends and coworkers, and in front of everyone I announce "You're pretty cute. You want to go out sometime?" She looks around and for the first time all night gets really coy and shy and fidgety and says, "um, what?". I said again, loud and clear "Do you want to go out with me sometime?" I can barely hear what she's saying but she's not shaking her head or anything, so I confidently put my finger up to my ear and say "Sorry, I can't hear you." while holding eye contact and a little smirk. She says "something, something...my boyfriend probably wouldn't like that very much" and then she nervously mumbles a bunch of things that I couldn't decipher. So I look around and say "Yeah, he probably wouldn't like that very much, would he...Is your boyfriend here right now?". She smiles and says "no", and I just keep staring directly into her eyes, hinting that it's her move. I can tell she was caught off guard by the whole thing (with everyone watching and all), doesn't know what to do, and is clearly looking for an out. We don't break eye contact for a good while, so eventually I show pity and simply say "I'll see you next time then"; confidently smiling like it was nothing. I hug the other bartender (she was sad I left so early), shake a few hands, and head home with just a name and a solid declaration of my intent.
While I know most people would say that I should have insisted on getting a number, I kind of thought that the 100% flawless interaction would have been cheapened had I done that. Or course she has a boyfriend. Never in a million years would this girl not have a boyfriend. I know I'll see her again, so right now it's open, and I like the position I'm in.
So seddit, if this were you, what would your game plan be?
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