If you’ve ever wanted to buy a drink for a stranger in a bar, you’re aware of how awkward the situation can be. You don’t want to offend this person with the wrong drink or, worse yet, come off as some kind of creep. Even if you get past the first step, the follow-up protocol is nerve-racking. Do you smile and wave when the person gets the drink or act like you don’t notice? Who should get off the barstool and talk to the other person first? No one knows these answers better than the omniscient bartender, so we asked some of our favorites how to buy a stranger a drink without coming off as creepy.
Get To Know Your Bartender
“A proper introduction inspires conversation, and to do that, it's best if you and I get to know each other. After we're on familiar terms, let me know when you see someone who sparks your interest. I can probably give you a hand with placing a well-timed, well thought out beverage in front of this person. After that, I feel it's proper for you to sit back and let him or her make the next move.” —Jack Zemke, Sauce & Barrel
“If a guy is eyeing a girl at the bar, first he needs to ask the bartender and make sure she is not with someone. Bartenders tend to get the best read on those situations. Then, if the coast is clear, it’s as simple as telling the bartender whatever the lady is drinking, he's buying the next one.” —Robby Rosello, Castile Restaurant
“I think buying a drink for someone across the bar is fine as long as you don’t stare at the person when he or she receives it. When the person eventually catches your eye, a casual nod works fine. When the person is done with the drink, make your way over to see if he or she would like a refill. This all, of course, depends on a person’s demeanor, so read the situation carefully.” —Michelle Farley, Strip House
Keep It Civilized
"The Up & Up is supposed to be a safe place to go for people looking for a calm, civilized space in which they can be with their friends—a sanctuary, so to speak. So our menu states that men are kindly asked not to introduce themselves to ladies. Bartenders can introduce them or ladies are free to start a conversation, or in this case, buy the first drink.” —Matthew Piacentini, The Up & Up