Lupa

YOU’RE DRINKING Whatever wine owner Amanda Prock tells you to order

“Intimate” doesn’t begin to describe this nearly four-year-old wine bar tucked into a hallway-size space on N Mississippi Avenue. So small is this Old World vino vault that you may well feel the need to hold your breath when you squeeze between the bar and the wall of wines on your way to one of the four bistro tables in back. But then again, that’s part of Lupa’s seduction: what’s more flirtatious than brushing someone’s back as you pass? The diminutive space enhances romance, as the din that rises from even a few patrons requires starry-eyed sippers to lean in to listen. Plus, the walls are lined with one of the city’s most varied wine collections—400 in all—available by the glass, carafe, or bottle (and to go). Paired with olives, cheeses, fresh-baked breads from Pearl Bakery, and, of course, your ravishing date, it’s an experience that’s sure to leave you breathless.

Landmark Saloon

YOU’RE DRINKING Kentucky Rose ($8): Bourbon, Peychaud’s bitters, club soda, on the rocks

Washed in candlelight, everyone looks better—fewer laugh lines, smoother skin, a flame-shaped twinkle in the eye. So with its 35—yes, we counted, 35—glowing mason jars, the five-month-old Landmark Saloon lets you put your best face forward for that first date. The heavy red drapes, doily-bedecked wine-barrel tables, and western-themed cocktail menu only add to the Lonesome Dove-esque ambience. (Just be sure to give your eyes time to adjust to the darkness when you walk in, lest you play Gerald Ford.) Added bonus: should you reach your drink limit before you run out of conversation, a gaggle of board games—from Trivial Pursuit to Life—gives you reason to linger just a little bit longer.

23Hoyt

YOU’RE DRINKING Zero Martini ($9): Beefeater gin, Carlos 1 brandy, caperberry

Big and open, 23Hoyt doesn’t exactly scream “date,” unless you’re talking about a business date. You know the kind: out-of-town executives are visiting and you need to entertain (read: impress) them, or your happy-hour meeting with a potential vendor could use a little enlivening. A follow-up to Bruce Carey and Chris Israel’s renowned Zefiro, 23Hoyt earned early acclaim: a year after it opened, the Wall Street Journal even dubbed it home to Portland’s “power tables”—the spots where A-list visitors like Jennifer Aniston and Mikhail Baryshnikov and locals like Gus Van Sant like to sit. (Hint: most of them are upstairs, on the mezzanine.) Four years after that, it’s still going strong. With thoughtful signature cocktails, an expansive happy-hour menu, generous windows for gawking, and the prospect of rubbing elbows with the elite, 23Hoyt promises to help you lighten the mood (and maybe land the deal). Should the meeting go your way, the menu boasts at least 10 different sparkling wines to help you celebrate.

Gold Dust Meridian

YOU’RE DRINKING Gold Dust ($7): Champagne and grapefruit juice, served up

Dressed in dark woods, exposed brick, and a wall of windows framing the bustling Hawthorne scene, this three-year-old love nest hums with sensuality, from the bare-breasted woman in the velvet painting above the bar to the scorpion bowls (drinks meant for sharing) on the menu. No wonder the love-soaked Gold Dust Meridian regularly features stylish couples canoodling over cocktails in its recesses. Of course, a drink can speak a thousand words, so you’ll want to choose carefully from among the Meridian’s 21 signature drinks. One suggestion: the Hibiscus Royale (champagne and wild hibiscus flower), which purrs romance in a fluted glass. Order it at the tea-lit bar, and retire to one of the vinyl booths, where you and your date can whisper about what happens next.