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16 First Date Spots for Every Kind of Portlander

A dating guide to restaurants that can make anyone look good

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While it's no secret that Portland is teeming with attractive singles (particularly of the artistic persuasion), Portlanders are often faced with the all too familiar conundrum: Just where do you take someone on that crucial first date? More so, what kind of vibe should you go for? Well, these restaurants and bars can likely accommodate your dating style, no matter if it's swanky and sleek, cozy and romantic, flannel and IPA, or awkward and shifty.

Did we miss the most romantic restaurant ever? Let us (and the greater world of Portland singles) in on your secret in the comments below. (The points on this map guide are not ranked but organized geographically).

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The Bye and Bye

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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.

The Box Social

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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.

Wonderly

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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.

Liberty Glass

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Well-suited for shy, bookish kind, this off-the beaten-path nook is the ideal setting for a low-key date. Situated inside an old pink house tucked away from the commotion of Mississippi Avenue, dates will be charmed by its cozy living room-style digs accented by warm earth tones. Order a Toffee Coffee and get comfy by the front porch fireplace or one of the cushier seats upstairs.

Secret Society

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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.

Picnic PDX

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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.

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.

Pope House Bourbon Lounge

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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. 

The Observatory

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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.

Departure

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The futuristic and upscale Departure Restaurant + Lounge is the place to go to see and be seen. Situated atop the Nines Hotel, it has killer city views and exciting cocktails, and the restaurant serves eclectic Asian dishes by Top Chef finalist Gregory Gourdet. No awkward dietary restriction questions needed; options for vegans and gluten free diners are abundant here.

Punch Bowl Social

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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.

The Pied Cow

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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.

A Roadside Attraction

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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.

Sapphire Hotel

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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 sets a tone for the amorously inclined.

Bible Club

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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. 

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The Bye and Bye

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.

The Box Social

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.

Wonderly

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.

Liberty Glass

Well-suited for shy, bookish kind, this off-the beaten-path nook is the ideal setting for a low-key date. Situated inside an old pink house tucked away from the commotion of Mississippi Avenue, dates will be charmed by its cozy living room-style digs accented by warm earth tones. Order a Toffee Coffee and get comfy by the front porch fireplace or one of the cushier seats upstairs.

Secret Society

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.

Picnic PDX

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.

Andina

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.

Pope House Bourbon Lounge

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.

Tope

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. 

The Observatory

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.

Departure

The futuristic and upscale Departure Restaurant + Lounge is the place to go to see and be seen. Situated atop the Nines Hotel, it has killer city views and exciting cocktails, and the restaurant serves eclectic Asian dishes by Top Chef finalist Gregory Gourdet. No awkward dietary restriction questions needed; options for vegans and gluten free diners are abundant here.

Punch Bowl Social

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.

The Pied Cow

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.

A Roadside Attraction

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.

Sapphire Hotel

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 sets a tone for the amorously inclined.

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Bible Club

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. 

Related Maps