The first time I bought a girl a drink from across the bar was at Johnny G’s in Frisco, Colorado. She looked at the bartender, then at me, then grabbed her jacket and ran for the door. Done wrong, sending a total stranger a drink reeks of desperation. But done right, it’s pure class.
First, avoid looking like a perv. Don’t send a girl a drink when she’s with her boyfriend—even if he’s in the bathroom at the time. Don’t choose a girl more than 20 years your junior. Don’t send Jäger. Ever. Or whiskey. Or straight shots of vodka or tequila. Ideally, you should find out what she’s drinking. Barring that, leave it up to the bartender. Upon delivery, stare on casually, smile, raise your glass. Under no circumstances should you wave or wink.
Tip well before you try; you’ll need the bartender on your side. “If a customer is being friendly, I’ll want to mack him out,” says Virginia Smith, a bartender at MaxxFish in Whistler. Buy drinks for her girlfriends too: It says you’re not trying to separate her from the flock and implies that you’re rich. Try to have some contact with her beforehand—a well-timed bump on the dance floor, casual banter near the bar, a few playful glances, whatever works. There’s nothing more awkward than a bartender spending five minutes trying to point you out.
And be prepared for it to actually work. This is an icebreaker, after all, and you’ll need something to talk about besides powder days. “If a guy sends me a drink, I’ll usually go over and say thank you just out of courtesy,” says Ariana Snowdon, 22, of Jackson Hole. “I mean, unless he’s a total creeper.” So if you leave your My Little Pony T-shirt and thousand-yard stare at home, you might have a chance in a ski-town bar. —Pieter van Noordennen
Or Maybe You Should Just Go Talk to Her
Sending a drink is like wearing a “masculine” shade of pink—it works if you’re strikingly attractive, or it makes you look like a tool. Be aware that you’re putting yourself up for judgment based solely on one glance across the bar. If you look less like Jon Olsson and more like John Candy, stack the odds in your favor and actually talk to her. Smile, be witty, tell her you took time off from medical school to film with MSP—whatever keeps the conversation flowing. Then buy her a drink, and whatever you do, don’t mention having to clean your hot tub. —Hillary Procknow