1) What is the cold, hard probability that this woman finds you attractive? Assess your hotness now. I was a very friendly bartender, but you cannot mistake "professional jawing" for flirting. Female bartenders flirt. It's how we pay rent. Don't mistake it for liking you just because there's no pole and we're fully clothed.2) Are you fully prepared to step in a giant pile of awkward if she says no? We flirt, but there is an unwritten rule that we can flirt, because you're not supposed to call us on it. If this is your regular bar, you are committing a social offense so egregious I almost want to smack you myself. Of course (deadpan), there's always the chance that you're meant for each other. Please see question #1.3) What's your plan? You have to have a plan. "We should go out sometime" is not a plan. Do the two of you share an interest? Maybe an author or certain music? Bring an appropriate but small gift. How does she react? Positively or politely? (Take a friend for an honest assessment.) Take another baby step from there if you dare.4) Only ask her out if it's to do something. Dinner's no good. (She works nights, duh.) A bike ride? Kayaking? She has days off; chances are she's got a daytime hobby, so latch on to that. Something that has a clear end time works best, but nothing that could lead to a nightcap. Remember, she witnesses 1:30 a.m. hookups all the time. Put her in that situation at your peril. Whatever you do, don't be eager. She sees through you like glass. It will be like putting the moves on Bruce Lee. So don't try, just be.The female bartender is perhaps the most jaded, cold, walled-off, and unapproachable member of the female species. Remember, she spends her evenings listening to men bullshit women. She gets hit on by the douche with the popped collar while his girlfriend's in the bathroom. She mentally counts the number of sentences it takes a guy to work sex into the conversation, because they always do. In her mind, men are predictable, ridiculous animals who can rarely be trusted, or worth her time. You still wanna date a female bartender? Well, you better be a pretty exceptional guy.Good luck, and duck, you sucker.