1. Bartenders are paid to be nice to you.
This is the inherent conflict in most bartender-patron relationships. Not only is it my general job description to be nice, but you, the patron, determine how much I get paid — via tips (hourly wages for bartending are literally next to nothing). Of course a bartender should be tipped for a job well-done, but I want to be rated on the basis of “she promptly and pleasantly got me my drinks,” not “she laughed at my annoying jokes and smiled coyly.” When I'm nice to you, I'm doing it because that’s my job, not because I want to sleep with you.
Yes, a bartender should always be pleasant, remembering regular customers and chatting when it’s not busy — this is the mark of a great bar atmosphere. I used to work a pretty boring day shift at my bar, so I often made casual conversation with anyone spending their Wednesday afternoon drinking. This got me in trouble in terms of guys asking me out, because the additional attention made them think we had a special connection.
In case you’re not sure how desperate you look, the note above was left for me by a firefighter at least twice my age.
2. Remember the drunkenness graph:
Yes, bartenders occasionally drink while we're on the clock. But nowhere near as much as the people we're serving. I probably didn’t rip shots before arriving, like you did. And unless I own the bar or am one of the dancing girls in knee socks at McFadden’s, my bosses likely don’t encourage blatant drunkenness on the job (I mean, come on, does yours?).
So pause for a second and consider how you sound to a sober person. Answer: drunk. Check yourself.
Seriously, being asked out when you’re behind the bar can be described as nothing but The Worst.
Scenario A: I like you. Great. I still have to serve you drinks or the bill, the tip has suddenly become way more awkward, and in general, I've violated the “don’t date customers” rule.
Scenario B: I don't like you. I'm left stuttering about how I have a boyfriend (if I don't, I'll lie) or I'm not allowed to date customers. Then I'm stuck awkwardly giving you beers while avoiding eye contact and trying to appear casual while reading AM New York in the corner of the bar or hand-drying dishes for the rest of my shift. Note to the world: I never actually want to be reading AM New York, and dishes dry themselves. I’m avoiding you by trying to appear busy at a job where the only task that can keep me busy is human interaction.
If you're ever a bystander in a bar and see this happening, the best thing you can do is what one wonderful woman did for me: Loudly comment on how tactless it is to ask someone out when they’re stuck at their job. Use the phrase “CAGED ANIMAL” to make the offender feel extra pathetic.
4. It's just not going to work.
Unless we magically fall in love and get married (not likely), the best that could happen is we're going to go on a few dates, maybe hook up, and realize it doesn’t work. Then I lose a customer and you lose your favorite bar. It's just not a good road to go down.
5. If you MUST make a move, get the timing right.
If you truly think a bartender is the only person in the world you will ever be happy with, at least wait until she’s off her shift and ask to buy her a drink. See how the conversation goes when you’re both safely on the same side of the bar.
But hey, we can still be friends! Here's a little free advice for how to get on a bartender's good side:
Don’t order annoying drinks.
Yes, I know how to make normal, non-vile drinks like a Manhattan or a cosmopolitan. But if you're ordering a drink that includes flavored liquor, or has more than one kind of juice plus grenadine, first, don’t, because you’re asking for a hangover. If you must, be prepared to tell me what’s in it.
Also, it's not cute to ask a bartender to “invent” a drink for you unless it's a really slow night or you actually know her.
This is a real thing. A lot of bars are instructed to make between 10–25% of the drinks free (so yes, we do know they’re overpriced), so it can pay off to stick with one bar in a night rather than hop around. I gave buybacks to loyal customers for every fourth drink they ordered, and for every fifth to someone I didn’t know.