I'VE NEVER KNOWN how to talk to bartenders. Sure, I can say, "Another tall whiskey ginger!" and "Check, please!"—but beyond the basic language of commerce, I'm usually at a loss. If I try to riff, a part of my brain always wants to say, "A thousand thanks for the libation, my good sir," and it takes effort to shut down that destructive impulse. But I've also watched around a million episodes of Cheers, and I choose to believe that a good relationship with one's bartender is a true and noble thing.
To get to the bottom of this social conundrum, I decided to do some day drinking at my local, the Bonfire Lounge (2821 SE Stark), where I'm mostly known as "Another tall whiskey ginger?" and "The guy with the book."
I described my mission to Rachel, one of the Bonfire's regular bartenders. Rachel hails from Spokane, a town she described, in bartender terms, as "the land of blue drinks and Red Bull in everything." Portland, by comparison, is pretty laidback: "Vodka soda, whiskey soda, stuff like that." Rachel's specific advice (aside from "tip awesome") was to have your order ready by the time you get up to the bar, especially if there's a rush.
On the subject of actual conversation, she said two minutes is the average amount of time your server has to shoot the shit before they have to move on to something else. So a little light observational humor or an anecdote, not your life story or a summary of Wagner's Ring Cycle.
Up the street at Stammtisch (401 NE 28th), bartender Neil told me the phrase that gave him the thousand-yard stare back in Eugene was "Make me something yummy." He explained that he liked talking shop and giving recommendations, but those are the luxuries of a lightly populated barroom. He also noted that younger drinkers tend to treat a bar like their personal clubhouse, as opposed to a pleasingly dim public space.
At this point I was fairly tipsy and it was only 3 pm, but I decided to make one last stop at North Bar (5008 SE Division), where the bartender, Holly, noted that ordering a flaming anything in a crowded bar is unlikely to make you many friends, and ordering an Irish Car Bomb at any time is an immediate red flag.
What did I learn on my wobbly odyssey? Mainly that a good server isn't going to tell you when you're being obnoxious unless you happen to be writing for a newspaper. So context clues are important. Don't order cocktails at your local pub that're better suited for the fancy duke of a neon future, and especially don't do that at peak hours. And once everyone is feeling good about the exchange of booze and cash, you can move on to more convivial topics, like... sports, probably? I can't help you with that part.