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, including grilled “cheese.” 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.

Recalling the bohemian days of Arthur Rimbaud and Paul Verlaine, this candlelit, 1907 Victorian-era lounge offers old-world spirits, including absinthe, for myriad vintage cocktails. The venue also has a separate room for concerts.

With creamy velvet booths and cocktails that are as fun to say as they are to drink (like the Turning Violet with hand-spun, made to order lavender cotton candy garnish), Picnic PDX is as sexy as it is playful. It’s quiet enough to hang on a date’s every word, and with a solid happy hour menu, thoughtful beer and wine options, and complete dinner menu (should things go well), diners will be impressed with this spot that boasts a classy feel without breaking the bank.

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.

For tequila and mezcal lovers, this chic rooftop bar at The Hoxton Hotel features stunning views of the city with prime seating for colorful sunsets. It’s the perfect balance of noise— not too loud, but loud enough that there’s no pressure for intimacy. The Spicy Margarita is a good way to kick the date into gear, and when things go well, the hidden speakeasy downstairs is a good second stop for refined and classic cocktails in a darker, cozier location. 

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.

Punch Bowl is one part bar and restaurant, one part arcade, karaoke bar, and bowling alley, making it a no-brainer for those terrified of spending two hours staring awkwardly across a table. Wow your date by letting them win at pretty much any kind of game you can imagine. Or if the date turns out to be a drag, you can at least busy yourself with some skee ball sessions.

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 have 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.

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.