As both a 20-something and the editor of Eater Portland, I often end up recommending date restaurants to friends. What people have in mind for first dates, however, varies dramatically. For people desperately hoping to exude a low-stakes energy, a dive bar patio or a pint at A Roadside Attraction is a common choice. Some people are looking to impress, nabbing a reservation somewhere like Oma’s Hideaway or the bar at St. Jack (depending on what “impressive” means to you). Some people are really looking for a distraction from the pressure of first-date talk, opting for an activity-centric option like Ground Kontrol or Mox Boarding House. Thus, pitching a first date locale can feel like a test.
Based on my very unscientific, entirely anecdotal data, dating in Portland often involves sifting through a pile of mediocre matches; however, I’m not entirely convinced this is a) specific to Portland, or b) fully based on the actual people involved. Setting or environment can significantly impact the success of a date, even if there isn’t a clear spark. An overly stuffy dining room, or an excessively loud bar, can make conversation tricky. For some dates, external stimuli — pool tables, pinball machines — can help loosen people up, while others can find it distracting. Picking a location for a date isn’t just about your own personal preference, either; it’s about the dynamic with the other person. That neighborhood steakhouse might have worked great for a Friday night dinner with your ex, but feels entirely weird and wrong with your latest Tinder match. So it is tricky to find the right spot for a date; that’s why people so often ask for help choosing a place.
When recommending locations for first dates, I am more inclined to recommend clusters of bars or restaurants over a single location. The logic: It makes room for improvisation, based on the nature of the date. For instance, booking a table at Scotch Lodge leaves room for a second drink at Sousol if the vibe is sexy, a daiquiri at Rum Club if the mood is lively, or a tallboy at the Slammer Tavern for something laid-back. Meeting at the Prost Marketplace pod for a bite could turn into beers by a fire pit at the Rambler, or low-lit Old Fashioneds at Interurban, or a stroll with ice cream cones from Lovely’s Fifty-Fifty.
But for the most potential spinoffs, the intersection of 30th and Killingsworth is the move, with a condensed selection of wildly varied options for dinner or drinks; nothing is more than a one-minute walk away. When it comes to first stops, your casual-to-romantic spectrum is fully represented here. For the most easygoing dinner option, start at Toyshop Ramen: As noted in our recent map update, the cocktails are goofy and reference-packed enough to be a conversation starter, the food is interesting and accommodates a wide range of diners, and the actual space is filled with fun things to do while you wait, or if the conversation falters — pinball, Baby Pac-Man, Big Buck Hunter.
Moving up the spectrum just slightly, Gabbiano’s has a bar for casual conversations and marinara-filled fried mozzarella shots, which can graduate to a two-top for a Lady and the Tramp spaghetti situation; however, the boisterous quality of the dining room will keep things from feeling too amorous. Across the street at Expatriate, popping in for cocktails involves vibe-y music on the record player and mood lighting, hitting the sweet spot between cool and sultry; the food and drink is creative enough to instigate conversation, with things like lemongrass beef wonton nachos and dealer’s choice cocktails.
For something a little quieter but also relaxed, Wilder is giving neighborhood-watering-hole in the best way, with super approachable food, balanced cocktails, and a mellower atmosphere. Kicking things up a notch, Clandestino at Lil’ Dame and Yui both deliver ambiance, candle-lit tables in an intimate dining room; the food is exciting at both restaurants, with wine flowing as a worthy accompaniment. But when it comes to high romance, it’s extremely hard to beat the dining room at Dame, whether you’re there for the main restaurant’s Italian food or the Monday through Wednesday Chelo service — the cerulean tones, seriousness of the food and drink, and soft lighting make it one of the stronger date night options for unapologetically lovey-dovey couples.
Perhaps what works best about all of these spaces is that many of them can shift roles, and stopping in for one snack and drink before hitting up a secondary location isn’t exactly unheard of. Starting with a drink at Toyshop or Expatriate can escalate to dinner at Clandestino or Chelo, or it can be more of a Wilder burger or Gabbiano’s chicken Parm situation. Maybe the intimacy of dinner at Dame can roll into a party vibe at Toyshop. If things go really well, maybe things end with an espresso at Extracto or a pastry at Flour Market in the morning. But for now, let’s stick to drinks, and see how things go.