In general, I think that like waitresses, the bartender is a sucker play. Both groups will string you along to get you tipping better and buying more, but something will almost always come up that prevents sealing the deal.
That said, one of my SC wingmen who tends to have a penchant for waitresses and bartenders (insert eye roll here), came THIS CLOSE to scoring a bartender for OTC. She had agreed to it, as long as they did a "double date" with me and my ATF, although the bartender understood that we'd be adjourning to separate hotel rooms after dinner. However, my buddy is a bit self-destructive, and did the dumbest thing ever: started talking politics with her. This may be a shocker, but it turns out, a middle-aged law-and-order conservative has a diametrically opposite view of the police from a 20-something tatted-and-pierced this-job-is-the-pinnacle-of-her-life-achievement-so-far strip club bartender. He basically told her to fuck off and canceled. I told him to stop fucking talking politics with the girls, he robbed himself of what could have been an amazing experience with a smoking hot chick.