Teardrop

Years ago I first went to Teardrop on a blind date late one weeknight evening and it was definitely a great choice. Although that date went nowhere, I keep going back to Teardrop for their fantastic cocktails and stellar service. The staff goes out of their way to make you feel like a regular even if it’s your first time there. Super attentive and great recommendations. On a weekend, Teardrop tends to fill up and becomes much more of a social scene. Industry people will tell you: Teardrop is the place to go for a great cocktail and you’re sure to run into the city’s bartenders after their shifts.

Secret Society

This place has all the charm of a speakeasy without the pretense. It’s dark and intimate with seating for less than 20 so you’re guaranteed exceptional service from their knowledgeable bartenders. The menu is divided up by spirits and features classic drinks (think champagne cocktails and absinth fountains). Although they do serve food and offer happy hour selections, Secret Society is really best while you wait for your dinner reservation downstairs at Toro Bravo for which you’ll want to save plenty of room to enjoy as many tapas plates as possible.

Clyde Common

This is one of my busier picks for a great drink date so that might not be for everyone. But if you’re game it’s definitely great for people-watching and eaves-dropping. I usually visit here at happy hour which boast one of the booziest yet cheapest drink in town: the Nasturtium. The drink, like the whole of Clyde Common, can be enjoyed just as much at non-happy hour times and the late night hour is particularly fun.

Driftwood Room

Yep. I’m going to make the claim: the Driftwood Room is the most romantic date night spot in Portland. Once your eyes adjust to the dark atmosphere. But that definitely adds to the experience. You can barely see the person sitting next to you in this cozy little cave of the Hotel Deluxe. And ladies like me know low light is the most flattering of lights. Besides the intimate atmosphere, the drinks and food are fantastic. Sitting in the bar at the Driftwood Room sipping on a cocktail leads to day (night?) dreaming about your alternate personae and make syou feel like you just maybe, in this lighting and with the aid of cocktail, could be as glamorous as Veronica Lake.