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The answer to this question is pretty universally “no,” if we’re being quite honest. Bartenders (and other service workers) are already dealing with an imbalanced power dynamic where it is literally their job to make you feel like they like you, and there is a very real risk that rebuffing your advances may lose them their job. Their income, and often even their employment, is almost entirely dependent on how convincingly they act like they like you, and on how much you like them.
That said, if you’re certain there are sparks between you and your bartender, there ARE ways you can go about making the connection without making it weird. Whether or not you should, however…
Now that you’ve made it through the chart, listen up:
DO NOT directly ask your bartender (or server, or cashier, or barista, or whomever) out. They literally cannot walk away and have no choice but to stand there awkwardly smiling at you. Putting them on the spot is 110% completely inappropriate.
So what do you do? Write them a note. Some variation on the following:
“I think you’re really cute, and I’d love it if you wanted to meet up some time when you’re not working. Here’s my number. There’s no pressure, and I promise I won’t make things weird if you don’t use it.”
That last bit is EXTREMELY IMPORTANT. If you absolutely must hit on someone who is literally being forced to serve you, it is imperative that you let them know that you won’t hold it against them (or make their lives hell) if you’ve completely misread the situation and they’re not actually into you.
ADDITIONALLY, your phone number is not a tip. Trust me. If you want even the slightest chance of that bartender calling you, you had better tip extra-well. And remember, they don’t owe you anything but the drinks that you’ve ordered.