Backstory on some of this, if anyone is curious and wants to read:
how-to-leverage-the-other-girl-vt153265.html
Basically, I am a regular at a local bar and have become friends with pretty much everyone who works there. The weekend DJ is my roommate, which is why I frequent there. I am also in an in-house dart league that plays there weekly.
So this bartender, who just turned 23 (I am 24), has been giving me plenty of IOIs but I am not sure if she is working the bartender/client angle or is genuinely interested. We have our little inside jokes, such as rubbing hands on each other's faces or throwing ice at each other. Last weekend she was in the bar for her birthday, not working. She asks me to dance because it is her birthday, so we dance for a second. Then she tells me to dip her, leans back, and then says I am not strong enough. I know she is joking, so I give her shit back and she tries to say I didn't let her finish and she meant for her fat ass. So she keeps trying to grab me and prevent me from leaving, and basically pushes me up against the wall with her ass in my crotch. I probably should have done something here but I failed to.
Fast forward to this week, on V-day. A buddy and I go in there for female desperation day, its pretty dead. This bartender comes in to work while we are eating, and comes over, leans over the bar and gives me a kiss on the cheek. I was taken back a bit, since I had never seen her do that to anyone else. She talks with us for a bit, trying to qualify herself by telling me how she is going for her Master's degree and how she has supported herself since she was 18. Eventually the other bartender comes in, a guy. He tells me about a party he is having the next night for another regular I know. He tells me to take down his number, and the girl bartender comes over and asks me if I want her number too. She walks away before I can get it, but I hand her my phone later and tell her to put her number in. She does, and puts it as "*name* Loverrr".
Go in the next night after the party, sit down at the bar with the other guy bartender and some girls from the party. Its busy, but she catches me laughing at her every now and then when she fumbles around behind the bar and throws ice at me while laughing. She shows me her new shoes and blames the fumbling on them. One of my buddies got really drunk that night and I had to take him home a little after close, so we didn't chat much that night. Next day I text her asking if she is working, she says yes and to come see her. I go in with my buddy and his girlfriend, don't sit at her end of the bar. Shooting the shit with the other bartender (the one who had the party) and she comes running over and again leans over the bar and kisses me on the cheek. We talk for a bit, she complains that I am not sitting at her end of the bar. I told her I'd come over in a bit, but never did. She comes over at randoms times and starts talking with us, tries to get me to buy her a shot. I tell her to give me a free shot, but she says she can't. She then tells my friend and his gf about the time she came in (not working) and I was sitting with some girls and was being short with her so she asked if she was cockblocking me and I said yes... Then she said she was hotter than them anyways. I guess they were mean to her on NYE when I went in with them, and I just told her not to worry about it (jealousy FTW).
So this is where I am. My buddy thinks I have a shot, as do I, but I'm not sure how to proceed. I have heard she doesn't want to date anyone right now, and neither do I, so I'm not sure if comfort building will work. Another bartender is having a going away get together at a different bar, I'm going to see if she is going. Might see if she wants to ride together, and if I can crash at her house that night. Her roommate has also been giving me IOIs, even though I have never actually been introduced to her. I'm not sure why this bartender flirts with me, as she is pretty standoffish to most other people when she is working.
Any input on this, how I should continue? I'm thinking I need to show a little more interest than I already do, but I don't want to scare her away or make it awkward if I push it too far... Basically I am afraid to fail.
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The hottest ginger you'll ever meet.
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