How Do I Buy a Stranger a Drink?

Strangers Drinking at a BarDid you ever see that scene in a movie where somebody buys a drink for someone they don’t know and they go on to become lovers, best friends, business partners, or a superhero duo that saves the world? How many times has that happened to you in real life? For that matter, how many times have you bought a stranger a drink in real life?

Buying a drink is kind of a big deal. It creates a minor sense of obligation in the person who receives it, assuming that they choose to accept it. There’s a potential for rejection, too—even a big theatrical rejection with the drink being thrown in your face. The buying of a drink expresses interest of some kind in a stranger, and that is often a big step to take.

How should a man buy a woman a drink?

Buying a woman a drink is probably the most tried-and-true, time-tested method of approaching a woman that there is. Too bad it’s still not easy. At least it’s a generous gesture that shows you’re willing to spend a little money on her.

One approach is to first scout the woman out a bit and see what she’s drinking, then just go ahead and order her one. This is slick when done well, but if you do it clumsily or with the wrong type of woman, you’ll come away looking like a presumptuous jerk or a stalker. Perhaps an easier way is to just walk up and ask “Can I buy you a drink?” It sounds crazy, but it just might work.

How should a woman buy a man a drink?

This is a pretty easy scenario to resolve—a woman can buy a drink for a man pretty much however she wants to. She can ask him what he’s drinking, ask him if she can buy him a drink, or pretty much order whatever the heck pops into her head and he will probably drink it, especially if he finds her reasonably attractive.

The harder part with ordering a man a drink is the aftermath. When a woman buys a man a drink, he will either assume that she is an aggressive, powerful woman who goes right out and takes what she wants, or that she’s desperate. Either way, he’s expecting to get laid tonight. In other words, don’t use this move unless you’re serious and have a great exit strategy planned in case the guy turns out to be a jerk.

How should you buy a friendly drink?

The friendly drink is probably the trickiest of the drinks purchased for strangers. Honestly, when you’re purchasing this kind of drink you almost have to get past the stranger phase first, otherwise they will assume your interest is romantic—unless they’re a wino, in which case they’ll pretty much take whatever you offer with a smile and a burp.

In most cases, you’ll want to buy a friendly drink after you get to know the stranger at least a little bit. Whether you see this person as a potential friend, kindred spirit, business associate, or someone you hope to knock over a bank with, you’re probably best off sitting next to them for a little while and making small talk. Hopefully, at some point you find a topic or two of mutual interest and have a real conversation. When the stranger’s drink goes empty, it would be natural to ask if you can buy them another.

How should you buy a celebratory drink?

The celebratory drink is one that is best done en masse, but it doesn’t have to be. If you can afford it, there’s no quicker way to make friends out of strangers than to walk into a bar in Wrigleyville and say “The Cubs just won; the first round is on me!” Unfortunately, in that particular example you might have to wait a few months for the chance to do it, and you would never be able to do it during the playoffs, but you get the point.

Not all of us can afford to buy a round for a full bar, so there will still be times when we celebrate with one or two select strangers. Maybe you just got a promotion at work, or maybe your divorce was just finalized and you need to celebrate with somebody. One of the best ways to do this is to just tell the person next to you what you’re celebrating and ask if you can buy them a drink so you can toast your good fortune. Most people would be fine with this.

Buying a drink for a stranger may not sound like rocket science, but it can be tricky and it can be intimidating. Knowing how to do it under different circumstances can help to give you the confidence you need to do it without looking like a creep, a geek, or an alcoholic. At any rate, have you seen the price of alcohol lately? Realistically, who’s going to turn down a free drink, anyway?