Today, I went out with my brother to a bar. Sunday night, so it was dead. Maybe 6 people in the whole place including us. Enter bartender. HB9, huge tits. My brother's eyes are about to plop out of their sockets. He starts ordering drinks and trying to chat up the bartender. She's receptive to him, because the place is dead and she's pretty bored. I ask for a water (I don't drink at all) and she questions me with a, "Not drinking tonight?" my brother answers for me and says that I'm the designated driver. So my brother and I are talking in Russian between each other, with the bartender coming up every now and then and cherping in her two cents about this or that. My brother begins to spit game (he's a "natural" who takes the high risk-high reward approach) and as he's getting drunker, the bartender sees that he's blatantly attracted to her. For my brother, the game was over before he finished his first drink.

While my brother was knocking down drinks and chatting up the bartender, I was working on my acting career, getting ready for the oscars. I consider myself to be cordial, respectful, polite and someone who has empathy. When I saw how hot the bartender was, I (very reluctantly) put my proper disposition aside. Game on. I interrupted the bartender to speak Russian to my brother. I did not smile at her, like every other guy at the bar. I watched the big screen television and did my best to ignore her when she wasn't around talking to my brother. (Every other guy was eyeing her as she moved from one side of the bar to the other). I didn't speak to her much, but everything I said was a full on neg. I asked her if she went to bartending school. As she was explaining how you don't really need it to work at some places, I broke eye contact with her as if I'm so bored and started to watch the big television behind her as if I'm not even listening to her. In order to "save face" from this awkward slap in the face to her, she turns to my brother and starts telling him the rest of her answer. I pretend she's a no one and start playing with my phone. Then, I told her to keep her hands off of my brother (my brother is engaged) and that I'll be watching her. At some points, I was just plain rude. I noticed that she would re initiate conversation with my brother, just to hang around an area where I was sitting. I noticed with my peripheral vision, that as she was talking to my brother, she made micro eye movements to see if I was looking at her as she was talking to my brother.

I continued throughout the night to be condescending to her and be very dismissive. After she answered a question, I simply said, "Thank you.". With a tone that signals, "okay you can please leave now". She would often stick around despite the tone being severely dismissive to re initiate chat with my brother, who was at this point pretty drunk and eating her shit up. At one point, my brother asked her when she was getting off work so they could have a shot of alcohol together, she carried herself well and said, "Oh I would, but my personal trainer is going to kill me". I then told her in a firm/ slightly pissed off tone to stop serving my brother drinks. She looks at him, then looks back at me. My brother interjects and says, "Hey, who's the paying customer, he or I?" (since I'm only drinking water, it was his open tab). She then looks at me and my brother says, "Okay, just one more". She says to me, your brother wants one more. I look at her and say, "Close the tab". My brother then starts to whine with the bartender saying, "Hey! I'm the older brother here, you can't listen to him." The bartender is reluctant to close the tab because of my brother's whiny attitude and "one more please" cries. She once more looks at me and says, "He just wants one more". I calmly but firmly, with a voice coming from my diaphragm say, "Close the tab". Now she looks a bit friengtened of me and does what she's told. My brother starts saying, "Omg, I can't believe you listened to him" to which she replies, "I don't want your brother to get mad at me".

After the tab is closed we sit a bit and this time, I talk to the bartender a little bit. She tells me that she used to work as a bartender at a strip club, that she used to model, that she used to be a centerfold. To that I reply, "You used to be a model?? Really?" but in a really, "You're to ugly to be telling the truth" tone. She says, "What you don't think I have what it takes?" to which I reply, "Hey, sorry I don't want to offend you". We end up leaving at my request, and I'm adamant that getting triangle cake is the most important thing in the world to me right now. I give her a tip of 3 dollars on a 60 dollar tab and say, "Hey thanks for putting up with my brother" and she says, "Oh sure haha, it was a pleasure meeting you guys". My brother asked her name, and she readily said it, however, she never asked either of our names, which tells me she's still just an attention whore. She doesn't care what our names were. And we never bothered to tell her. I should also mention that throughout our conversation, I mentioned that I fucked an asian girl on top of my grand piano (which was a total lie), in passing like it was no big deal, but I knew that this was necessary for the whole idea of preselection. Anyway, we end up leaving on a good note, with the bartender visibly slightly butthurt that I didn't drool over her like the rest of the venue.

My question is this, how many times do I have to go back and repeat this whole, ignoring, being a dick thing with the bartender before I can try and pull her? I feel like even if I gain some rapport with her, as soon as I ask for her number or to hang out, she'll be like, "Haha, another one bites the dust" and feel like she won me and that she can just reject me because she now has the validation of knowing that I do in fact want her? With hired guns, I almost feel like she is the one who has to break and ask for my contact information. Otherwise, when you become "vulnerable" and ask her out, they stop on that vulnerability. Any help with how to transition from attracting a hired gun, to actually number closing a hired gun would be greatly appreciated.