A More Perfect Union at The Teardrop Lounge
Given the chance, the beautiful Teardrop Lounge quickly proves that it’s more than just a pretty face. This, for example, is the Chanel No. 5 of cocktails: sexy, sophisticated, light. With Lillet Blanc serving as the base spirit, this drink is lower in alcohol than your average cocktail, which means you can go ahead and have a second with no fear of the dreaded cocktail-goggles. Apricot liqueur brings and earthiness to ground Lillet's floral side, and a barely noticeable bit of vodka rounds things out. If you want to continue the date, head to Oven & Shaker for dinner.
Love Makes You Feel Ten Feet Tall at Ava Gene's
Ava Gene's sets the stage for a date with just-soft-enough lighting and cozy red banquettes. This cocktail from star bartender Evan Zimmerman is meant to be lingered over. It's bitter, then sweet, then bitter again, balancing like a gymnast on a beam. Pungent Beefeater gin meets deep, bitter Punt e Mes, brightened and lifted with Macchu Pisco and grapefruit oil. A kiss of salt water seals the deal. Have one (or two) and if all is well, grab a table over on the restaurant side of Ava Gene’s for a bite.
The Scandinavian Scandal at The Secret Society
Tucked away and seductive, if there is a better bar in Portland than Secret Society to woo a potential love interest, I have yet to encounter it. Sparkling cocktails are a specialty of the house. This little number is made with local Krogstaad Aquavit, redolent with anise and caraway, softened by the addition of fresh lime and a healthy pour of Domaine St. Vincent Brut bubbly. Pro Tip: If you’ve got a good feeling about this date, put your name in at Toro Bravo before heading upstairs for a drink.
Ru Paul Sparkle Pony at The Box Social
How do you not order a drink called a Ru Paul Sparkle Pony? Pink and sparkly and fun, I think you’d have to work pretty hard to have a bad date while drinking one of these. Floral St. Germain brings out the richness of bright and bitter Aperol. They're shaken aggressively with Peychaud's bitters and a hint of grapefruit, then finished with a float of bubbly. It's fizzy lifting bliss. A little art deco, a lot of Portland love (complete with huge mural of PDX itself), Box Social feels at once casual and a little special. Looking for a bite afterward? Hit up EAT Oyster Bar or Lincoln.
Aviation at Interurban
Interurban is one of the more comfortable bars in NE Portland, particularly in the afternoon, when light fills the room, making their cocktails glisten even more enticingly than they otherwise would. Bar Manager Jeff Seymor builds this classic drink with Beefeater gin, creme de violette, and fresh lemon juice. He uses Maraska Maraschino instead of Luxardo—it's slightly more subtle and allows the other elements of the cocktail to shine. Citrus-forward and refreshing, the lemon and creme de violette swim together beautifully, while the Maraschino lends a gentle, balancing note of almond and cherry on the finish. If you're having a good time, head over to Lovely’s 50-50 afterwards for one of their fabulous pizzas.