How do I proceed? Simp take over/ service industry/ do I shit where I eat?
Alright yall, here's the situation, I work at this bar one or two nights a week as a fun side gig. Have never worked in a bar/ service industry so I'm not 100% on rules of engagement. The bar is attached to my apartment that's in an "affluent" area in Dallas, TX (Plano specifically for any of my NTX folks). I have been there now for about 4 months- I'm 28 years old and the rest of the staff ranges from 21-30 with there being only few 28+. I already have extremely high value due to the fact everyone knows I live in these very nice/expensive apts, I work in the Tech/ IT space in sales making great money during the day, I'm in great shape, and overall am just looked at as a "head male figure". Not to mention being known for being the bartender that gets the most tips, glowing reviews, and phone numbers while I'm on shift (no shortage thanks to PWF). I do not say all of this to toot my own horn- but more so to set the stage for this question- There is another bartender I work with that is insanely attractive. 23 years old and absolutely beautiful- 12/10. She is next level, unlike anything I have found on any app or really out in public since I've been here. She is super part time at this bar as well, 1 maybe 2 nights per week. There has been a lot of sexual tension built up for the last couple of months anytime we have worked together- which only happens maybe a few times per month due to schedules. She broke up with a guy that she had been dating for 4 months a little over a week ago. The first time I saw her after the breakup she was quick to tell me they had broke things off, that it was toxic, and that she wasn't going back. I had one single interaction with this guy and had seen him come into the bar while I was working- complete tool- I went on to roast the living fuck out of him after she broke the news (rightfully so) and then continued to dissect/ tell her exactly what went wrong- he was a young boy that didn't take any responsibility for his actions, couldn't look people in the eye which meant he was weak/ immature, shook hands like a little bitch, etc. She was surprised by how receptive I was after a single time meeting him. It matched what her friends had said and what she experienced and it turned into a running joke between us. It positioned me in a way that made her confident in my judgement Tonight was the first time we have worked together again since she told me she was single. We were flirting as usual when one of her friends came into the bar for a drink, I was taking her order when the hot bartender came up to greet her friend, the friend asked how her date went with other guy hot bartender's eyes got really big as though this was supposed to be a secret and awkwardly responded that "it was great". I jokingly called her out about not telling me about her "new guy"- she laughed and said that they were still just friends but hadn't hooked up/ gotten serious. Later, she went on to seemingly try to explain herself and sell me on this guy that was super nice and that she met a few months ago as friends and he treats her like a princess. Almost seeming to position me as her dating coach now. So I probe- how old is he, what does he do, etc? He's 22, works at a wine bar full time, and his mom/dad are loaded. All things that I roast the fuck out of and tell her that it sounds awfully similar to homeboy she just kicked to the curb- I position it in a way that is "Maybe he's not all that bad, though" so as not to come off too obvious that I just want her for myself. So towards the end of the night, this dude actually ends up coming into the bar for a couple of drinks. About half my size in stature, whole fucking tub of hair gel slicking his hair back, and sub par style. I see hot bartender greet him and she tells me that's the dude. I give him the head nod expecting him to be a man and introduce himself- he doesn't, makes weird dodgy eye contact and looks down at the bar top. I laugh and tell her "Wow, you definitely have a type, this guy doesn't have enough social awareness to even introduce himself or look anyone in the eye either." To which she gets embarrassed and asks if I was sure- of course, I was and I jokingly explained that he'll have to use his big boy words but I won't be going out of my way to introduce myself after that. Seems evident at this point that my opinion is extremely important to her. She actually tells this guy that he was acting weird and that he needs to introduce himself. About an hour goes by and we start to close the bar- he is hanging out after waiting for her while we are cleaning up. I'm joking with the rest of the staff, laughing it up with the other guests that are still present, when she finally gets the opportunity to take over for him, and forcibly introduce us. I start to ask him questions being as friendly as possible and treating him just like I treat everyone else- he's giving short answers, talking really quietly to the point that I have to ask him what he said, and really getting cucked out conversationally. After a few questions, I feel as though my point has been solidified and go on about my night ignoring him. All that to ask: Do I just go in for the kill and try to get this girl out solo "as friends" to tip toe around the coworker dynamic? Do I take a direct/ sarcastic approach and ask her to try going out with a grown ass man one time before settling for another child? The concept of trying to plow a co-worker is so foreign to me with all of my experience being in the professional world lol. Thank you in advance for any and all advice!