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Once it was a matter of course for a gentleman to buy a woman a cocktail. We know this is true: we saw it on Mad Men. Nowadays, the practice has been nearly lost to a tangle of ambiguous gender politics and the specter of roofies. Well, it’s high time we resuscitated this genteel art. Here’s how.

Be bold. Want a phone number? Start with a drink. Just don’t make this your first point of contact; catch her eye, strike up a conversation, or approach on the dance floor (and by “approach” we do not mean “grind”). Then suck it up and simply ask, “May I buy you a drink?”

Or not. If you’re enjoying the banter with the man sitting to your left but can’t quite muster the courage to make your move, be a mysterious benefactor instead. On your way out, cover his tab, or buy the next round, and leave your number. Just remember that buying a drink for a stranger is a kindness, not a contract—so don’t get upset if your cell stays silent.

Use a go-between. When bartenders aren’t overloaded, they’re often willing to play Cyrano (reason no. 407 to tip well). Send over a drink to that someone you’re admiring. If she accepts, be cool about it: raise a glass together, but don’t go bounding over to her bar stool like an overeager golden retriever unless you’re invited.

Use your savvy. If the barkeep is swamped, ask the charming fella beside you what he wants. Then work your well-honed bar skills to flag down the barkeep and buy the next round.

Do not be creepy. Even a little bit. You know what we mean.

This article appeared in the December 2010 issue of Portland Monthly.
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