A crucial date spot for vegans, this dimly lit Alberta space is where all the hip kids congregate on Friday night. The menu is all animal-product-free and hosts a variety of bowls, plates, and sandwiches. Not to mention the list of creative cocktails, all artfully named.

For a sophisticated yet mellow first date, this neighborhood “drinking parlour” excels at craft cocktails — even just watching the pyro skills that go into making some drinks is entertainment in itself. Dark tones and candles create an intimate mood, and there are plenty of snacks and small plates to choose from.

This bustling hotspot is casually elegant with beautifully warm lighting, the kind that makes anyone look good. Sip drinks that are classic with a twist, like the Banhattan (a banana Manhattan) or the Smith and Cross Negroni (which substitutes Jamaican rum for gin). Martinis and Manhattans are actually a drink and a half (with the half served on the side for refilling later), which makes the liquid courage easily accessible. And should your date be an aficionado of wine or beer, they’ll appreciate the carefully curated list, a compatible combination of domestic and old-world selections.

For dates seeking South American classics with plenty of Peruvian tapas plates for sharing, Andina is an ideal choice. For a more intimate and casual vibe, Bar Mestizo is a better fit than the main dining room — it’s a great spot for tapas, Pisco sours, live Latin music, and a fireplace to stay toasty during the rainy season.

As William Faulkner once claimed, “there’s no such thing as bad whiskey... Some whiskeys just happen to be better than others.” The latter rings true at this classy bourbon bar set in a Victorian house, which takes on a cozy, candlelit vibe come nightfall. Featuring an extensive selection of American whiskey, it’s a perfect place for a casual yet romantic first date involving drinks and a few small plates. Even more, happy hour lasts all day on Sundays.

Dimly lit and alluring, this romantic East Burnside bar attracts those looking for a curated cocktail experience. At Angel Face, you’re sure to get a cocktail you like — bartenders ask about your preferences before crafting a drink just for you. Menu items like the pickle plate or Castelvetrano olives give you something to snack on while getting to know each other. Dinner choices like lamb stew and steak with fries are available if the date is going well. 

This bar inside the Juniper NEXT hotel is an indoor jungle teeming with plants and vibrant decor. The cocktails list leans on the tropical side, seemingly imbued with sunny days, making for a perfect escape from the often dreary Portland weather. The adventurous food menu adds to the vacationing spirit of the space.

Not sure whether your date prefers a craft cocktail or a cheap pilsner? The Observatory offers a choice both chic and casual. Starry hanging lamps throw a romantic glow about the front room, with a mish-mash of modern, vintage, and industrial design. For a “divier” experience, meander the hallway to its sporty back-end bar, Over + Out, for some pinball and pool.

This Victorian house turned bohemian café is a classic second location for coffee and dessert after a date gone well. The charmingly romantic yet non-pretentious setting keeps it casual, but is cozy enough to make conversation linger. A popular place for Hookah, finish off the night on its outdoor patio with a water pipe and some hot spiced cider.

Those with a penchant for the bizarre can canoodle beside the fire pit at this cash-only, quirky Southeast bar adorned with seemingly random paraphernalia. There’s always something to talk about, thanks to the decor; lucky visitors might be able to secure a place for two on the porch swing. It's a casual, inexpensive night out, especially for those dubious Tinder dates.

No longer a hotel, nor a brothel for that matter, the seedy history that donned the Sapphire Hotel of the early 1900s has since contributed to its now sweltering persona. Hand-crafted drinks, candles, and rosy ambiance pretty much set a tone for the amorously inclined.

Entering Someday feels like walking into a dinner party hosted by your trendiest friend. With low light and a lively atmosphere, this Division street spot is somehow unfussy while serving craft cocktails, natural wines, and (occasionally) oysters. From Otto’s old fashion wiener to a simple salad to Portuguese sardines in tomato, there’s something on the menu for everyone’s palate. With non-alcoholic IPAs and Ghia cocktails, even those refraining from alcohol get the full experience of Someday. Outside, post up at a table under string lights for patio dining. 

An old-timey speakeasy that makes you feel like you stepped back in time, Bible Club is equal parts museum and cocktail bar. Everything about Bible Club tells a story, from the vintage decorations (all Prohibition period) to the antique crystal glassware and lace doilies. Seats at the bar provide entertaining views of mixologists who utilize house-made concoctions to whip up a host of clever and adventurous beverages.