Stretch a Sunday evening into a night of rock-’n’-roll food-hopping guaranteed to delight. Even at 6 p.m., Toro Bravo roars like a Spanish bullring, with music popping and sangria flowing. You want the cocido madrileño, a massive cauldron of chickpeas, marrow bones, chicken thighs, fresh chorizo, and a thousand years of Spanish grandma DNA. It’s dispatched with bowls of broth tasting like deep salami and platters of garlicked cabbage shreds, pickles, and smoky sauce for tinkering—enough to feed two daters and a chaperone. (Editor's Note: Trigger's Tex Mex sundae is no longer available) Hop next door to Trigger for an outsize Tex-Mex sundae as imagined by an ice cream mastermind: a heap of homemade chocolate ice cream, spicy Valrhona chocolate sauce, big roasty nuts, and, for good measure, a river of marshmallow madness.
Omakase at Tanuki ($20)
Step into Tanuki’s underground den and tuck into a dark nook for two. Speakers broadcast the house mood: hip-hop and Asian pop, fast and furious. Ambient light comes courtesy of Japanese zombie porn flicks in constant rotation. Even the food is unflinching, throwing in Korean spices, Japanese funk, and twisted sophistication. This is date night as imagined by Quentin Tarantino. From the set-your-own-price omakase menu, lay down your money and watch the parade of entertainments unfold. Where else can you feast on mile-long jellyfish strands, kimchi hanger steak, and mussels coddling outrageously creamy pollock tripe custard while watching chainsaw-wielding gals make their own mincemeat?
Late-Night Drinking Chocolate at Cacao ($6)
By day, Cacao stands as an icon of Portland food love and a headquarters for the modern chocolate-bar revolution. By night, this little shop of swooning pleasures transforms into the city’s sexiest secret, open until 10 p.m. on weekends. Friends and couples slip in to play cards, forage for sweets, and deconstruct the art of drinking chocolates, a kind of liquid dark chocolate pudding that pierces the deepest pleasure centers. Order a flight of three, each a different experience, from simple decadence unchained to pure cinnamon-chocolate exhilaration.
Duck through the wood-and-glass lobby, pass the hopping bar, slip into plush seats, and fasten your seatbelts. Compared to the multiplex, Living Room Theaters is an upgrade to first class, complete with food service at your seat. Thick napkins, real wine glasses, heavy silverware. Only in Portland can you canoodle at an indie movie, sip pinot noir, eat fresh popcorn from a ceramic bowl, nibble an arugula salad, devour a Cascade Natural beef burger dripping piquillo aioli (just $5 from 4 to 6 p.m.), and nab a local vegan truffle. Movie tickets fly for just $5 all day Monday and Tuesday.