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There's a barmaid that works in my local bar- I get subtle but definite IOI's from her. The thing is (as with most situations like this) it's a busy bar and getting any time to game her would is limited.
So, how do I approach the situation?
Bartenders or "hired guns" are extremely socially savvy and see many pickup attempts daily. Most are above average in attractiveness, and abhor beta behavior. Bartenders are my specialty, lol. As a 40 year old man, I do really well with snotty 20-something bartenders.
Here is what I can tell you, from my own experience and from listening to bartenders complain about their work in bed after I fuck them:
1. They hate guys who just stare at the TV, or who stare at girls and who don't take action. They call these guys "the starers".
2. They cannot stand shakiness in your voice, lack of confidence or guys, who beat around the bush. Name dropping and bragging also doesn't work.
3. They hear compliments ALL DAY from all kinds of men. It means nothing to them.
4. They like muscles. A lot. Most of the guys who come into their bar are 20-50 year old men, all about 30-40 pounds overweight, wearing sports team sweatshirts and looking and dressing like slobs (even a pair of nice jeans and a fitted T-shirt is better than this, trust me). They crave a man who can stand out physically from their sad clientele. If you looked at slobs all day, you would be pleasantly relieved to see a fit, decently dressed person.
So my 'right now" advice to you is this:
Don't dither. Don't hem and haw. As soon as you get a chance (hopefully when the bar isn't slammed, try to go during non-peak hours), talk to the bartender you like, make firm, DIRECT eye contact, and simply ask her to hang out after her shift in a confident tone.
That's it.
No "DIV's", or all the other weak ass scaredy-cat shit that hot bartenders don't respect. If she likes you, at the very least she will sit next to you after her shift and sip a beer.
Remember, going up to her bar by nature is submissive. She's in charge. She controls clientele, manipulates them, is the "boss of the arena". you must appear more confident and more emotionally-centered. This, combined with strong physical presence will have you hooking up with hired guns on a consistent basis.