Most of us have been there: sitting alone at the bar, nursing a drink and quite possibly some heartache, when you happen to spy someone across the counter who immediately grabs your attention. After a quick reconnaissance to figure out if she or he’s alone, you get the brilliant idea to buy the person a drink to signal your interest. It’s a risky play, but one that can definitely be worth making. With a bit of guidance, it might even work out for you!
We bartenders have seen it all: spectacular failure, glorious success, and everything in between. So while we’re generally happy to help, here’s some advice to make sure you don’t end up with that drink thrown in your face.
First and foremost, think about what kind of drink you’re going to offer. Your safest bet is whatever they were drinking before. If you’re enlisting the bartender’s aid, then definitely make sure to be polite. Be up-front: “I’d like to buy that person a drink—what have they been having?” Of course in a super-busy bar, there’s no guarantee the bartender will remember, but it’s a good place to start.
I also strongly discourage making assumptions based on the (apparent) gender of the target of your affection. Buying a man a whiskey drink or a woman a sweet, fruity one can be a really good way to offend someone before you have the chance to actually talk to them. It’s a bad idea to make any assumptions about what a given individual might want to drink based only on their gender or appearance, as personal tastes vary much more than you might think.
Beyond avoiding gender stereotypes, be aware of the message you’ll send by your choice of drink. Shots are risky, because they carry the not-very-subtle subtext of “I’d like to get you drunk enough that you’ll make a possibly poor choice later this evening.” Especially shots of tequila. A beer is safe, but also boring. My suggestion is a glass of Champagne or similar sparkling wine: It’s classy, nearly everyone likes it, and you look sophisticated. Unless you’re in the kind of bar where no sane person would drink wine, in which case you’re on your own.
Lastly, it really helps to have the bartender on your side. They’re the one who’ll deliver the drink, and you want them to sell you. As always, being considerate helps, as does recognizing when the bar is packed and the moment might not be ideal. Also, ask the bartender’s opinion. They might prevent an awkward situation, like asking to send a drink to the person he or she happens to be sleeping with. Now that was an interesting conversation.