Jeffrey Morgenthaler Bartending and Cocktail Advice Since 2004

Hey Bartender

I want to ask out a bartender at the bar I go to sometimes with my friends, but I don’t know how I should ask her out. Can you give me some advice?

G

Hey G

Asking out a bartender, especially a female bartender, can be tricky. On one hand, she’s probably getting asked out by every other guy that bellies up to her bar, and is more than likely getting tired of it. On the other hand, she’s just a normal person with a normal job, and you should ask her out just as you’d ask out any other woman. Just be yourself.

That said, there are definitely ways to your bartender’s heart. Here’s a few pointers:

1. Tip. Yes, she looks like she’s having a great time entertaining you, and everyone else in the bar. But the reality is that she’s here because she’s got bills to pay. A great way of separating yourself from the rest of the crowd is to tip respectfully yet extravagantly. Think of a tip that seems like too much money. Now double it. That’s what you need to tip, per drink, every time you go into her bar. And be respectful: never, ever talk about the tip. Just order your drink, tip well, and leave. She’ll notice you, believe me.

2. Don’t get too drunk. I know you think you’re really, really funny and interesting when you’ve had eight shots, but believe me, she doesn’t. She may be laughing right along with you and letting you think she’s interested in hearing what you have to say, but if you’re slurring and looking like a drunken fool, it’s all an act. And if you do get too intoxicated at her bar, don’t try to sober up there over the course of the next three hours. Call a cab and go home.

3. Show her that you’re respectful of other women in the bar. If you’re in her bar every night trying to take home every drunk girl you encounter, chances are she’ll think you’re a scumbag rather than the suave Cassanova you think you are. Be nice, be respectful, and chances are she’ll notice.

There you go, G, and good luck.