Less a bar than a meticulous little jewel box, Angel Face is a front-runner for the ideal date spot. The horseshoe bar, which occupies most of the space, has no cocktail menu—order based on spirit and flavor preferences, and they whip you something up. In warmer months, the patio (heated and covered) is probably Portland’s most Parisian, with tiny sidewalk tables and woven bistro chairs good for people-watching. Most come for the bespoke cocktails but, inconspicuously, Angel Face boasts a full French bistro menu: steak frites, pâté, duck confit, and a gloriously golden roast chicken. Come early and tuck into something hearty, or drop by for a Franco nightcap.  —Matthew Trueherz

The name Les Caves may be gone, but Ovum Wine’s dedicated tasting room, Bar Nina, still offers subterranean class for starry-eyed lovers and wine obsessives. The best seat in the underground wine cave is a nook built into the wall, where you can cozy up with a friend and share a bottle of wine: maybe one of Ovum’s own bright and vivid Rieslings, rare champagne, or a lush Italian red. Rioja-marinated Spanish sausage, goat cheese sprinkled with pollen, and the famous grilled cheese (Havarti and cheddar with a paprika dusting) keep things light and fun. If the sun's out, you can take the party upstairs to the Big Salt Bar, an enclosed garden space for sunny imbibing. Either way, it’s sure to be a memorable evening. —Alex Frane

When night falls, this light-filled, all-day café morphs into an intimate neighborhood retreat, illuminated in part by the embers of a mammoth brick oven. Prime seats are at the small chef’s counter—a bird’s-eye view of the cooking show in the open kitchen (and a blessing, if conversation lulls). The mode is casual, à la carte, and handmade everything. Smart moves: the supreme marinated olives, heated to order; a seasonal salad; and dessert, perhaps a lusciously frosted chocolate cake. Pasta is a house passion. But what is romance, if not splitting one of the city’s best pizzas, the Pomodoro?  —Karen Brooks

At this neighborhood fine diner, love comes in many forms: pristine oysters, hard-to-find champagnes, and heart-stopping chocolate chip cookies, rich and smoky. Coquine’s famed tasting menu has made its post-pandemic return, but à la carte is still the way to go for casual dates nights. Start with raw oysters or Ken’s bread and butter before splitting the bistro’s legendary roast chicken, served with seasonal vegetable sides. Caviar service doesn’t take itself too seriously— rotating options served in a jar with a little spoon to heap over sesame brioche. —KB

A trip to Heavenly Creatures can be the entirety of your night out. Though it’s technically a wine bar, presumably humble snacks (overseen by St. Jack’s Aaron Barnett) are more than enough to make a meal. Think chilled prawns with zippy Calabrian chile remoulade, Tim’s potato chips to dip in an aerated camembert mousse, and the cult-favorite yellowtail toast—a sushi-grade nod to a lox bagel. Grab a seat at the plant-filled, candlelit chef’s counter, or around one of the small pink terrazzo tables. Be it the warm light, the laid-back but festive mood, or the palpable reverence for the titular heavenly creatures (the bottles of wine), being here carries the ineffable feeling of “going out.” —MT

This pan-Asian Pearl District hot spot delivers big on ambience, with a glowing cherry blossom tree in the center and showy food and drink—cocktails concealed under smoke-filled domes, caviar service adorned with bamboo mats and woven branches, hot stone wagyu beef. The menu is expensive but built for sharing, with dishes to suit several moods, including lavish Peking duck, restrained nigiri, and small plates, shishitos to steamed bao. —KCH

Portland’s original offal-loving punk-rock bistro has food combinations that would make Escoffier laugh, plus a robust wine list. If that’s not your idea of romance, we can’t help you. You never know what might spring from the mind of gifted chef Gabriel Rucker, only that it will be interesting. The experience is tasting menu–only, the weird and the wonderful. Each course is seemingly from a different Rucker planet, with distinct omnivore and vegetarian menus. Meat courses might veer from black truffle beer can chicken to ox hearts with bone marrow sabayon. Veg people get the likes of cornflake-fried squash. Desserts keep the whimsy going, like almond mocha ice cream with a foie gras profiterole. —KB

From the agave-obsessed restaurateur Ketsuda ‘Nan’ Chaison and dessert maven Gabriella Martinez, Libre provides a stunning combination of cocktails and sweets. The dining room’s dark lighting and jewel-toned fabrics provide a lovely backdrop as couples dip spoons into decadent, intricately crafted cakes and sorbets, often topped with candy lattices, fruit gels, or even breakfast cereals. For imbibing, banter over glasses of mezcal spiked with strawberry cheong or mole syrups, or sip nonalcoholic concoctions that are just as thoughtful as the boozy versions. It’s the closest you can get to a Mexico City cocktail lounge without a plane ticket. —AF

A fixture on SE Hawthorne for decades, Sapphire Hotel offers opulent coziness with its dark, woody interior and low lighting. Its menu is chock full of date-night staples: rich, bold cocktails, sparkling wines, bacon-wrapped dates, tinned fish, and delicate lemon olive oil cake. Squeeze into the banquette with your partner for an Italian Coffee (a mad concoction blending an Irish coffee with a Negroni) or get there early enough to secure that seat near the fireplace, tucked in the back corner. —AF

Tommy Klus’s dark and sexy whiskey bar doubles as a food destination, with seats in cozy nooks or at the handsome marble bar attended by a crack team of cocktail experts. Chef Tim Artale makes familiar foods fun, delivered with bistro-quality plating. Oysters are a must, topped with playful granitas. Fried Brie sticks, clad in fine pumpernickel crumbs and pistachios, taste like elegant, cheese-oozing French toast. Some of Portland’s best pasta is found here (not to mention a world-class whiskey list). But the real date test: Are you going to share the monumental soft-shell crab sandwich or hog it for yourself?  —KB

Masquerading as a classy bistro on NW 23rd’s upscale strip, St. Jack is part of a modern wave of French restaurants pushing history book recipes into the modern era. Neo-Parisian flair melds seamlessly with the date night charm of the classy, dressed-down dining room. From rich pâté en croute to a humble but delicately roasted salmon to impossibly airy gougères (yes, remarkable cheese puffs), the menu is full of exciting but unpretentious bites to nosh between longing gazes. The wine cellar is deep. The dessert menu is loaded with nostalgic favorites like baked-to-order madeleines and mille-feuilles. If you’re looking to woo a certain someone with a penchant for the French, this is your spot.  —MT

For a lot less money than a getaway to Spain, Urdaneta offers the low-lit vibes, fortified wines, and parade of pintxos of a cool San Sebastián taberna, all on Alberta Street. Along with an impressive selection of vermouth and sherry (get a flight for the full experience), seasonal sangria and plentiful Spanish wine flow as couples lean in to whisper among the buzzing dining room. The open kitchen churns out an impressive slate of tapas and pintxos, imbued with the balanced whimsy and sophistication modern Spanish cookery is known for: think spherified olives (inspired by Spain’s famous El Bulli), aerated truffle potatoes, and whipped Mallorcan soft chorizo. —KCH