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A plant-draped ceiling and colorful rug lead to a bar.
The bar at Hey Love.
Hey Love

17 First Date Spots for Every Kind of Portlander

A dating guide to restaurants that can make anyone look good

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The bar at Hey Love.
| Hey Love

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. 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.

Free House

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Hardwood floors and leather banquettes imbue this casual neighborhood bar with warmth and sophistication. It’s as much the spot for craft cocktails as it is for cheap beers. The food menu offers bar snacks, charcuterie, salads, and meat-forward dinner items. Partially covered patio seating is available for those wanting an airy atmosphere. 

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.

Round tables are lit by globe light fixtures within Andina’s private dining room. Alyson Levy/Andina

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. 

Angel Face

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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. 

Hey Love

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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.

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.

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 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 set a tone for the amorously inclined.

The Richmond Bar

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This down-to-earth bar is the ideal setting for a casual date. Slide into a booth and let the laid-back environment calm the first date jitters. Richmond boasts a variety of aptly named cocktails, as well as a beer and wine menu. From shoestring fries to a meat pie with wild boar and veggies, the food menu is unassuming but enticing. Prefer outdoor seating? Richmond offers a heated patio out back, complete with a fire pit. 

Lauren Massie/The Richmond Bar

Someday

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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. 

A paved alleyway in between two buildings, one pink and one painted with a mural, with Christmas lights criss-crossing across the two buildings.
The alleyway leading to Someday.
Dina Avila/EPDX

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. 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.

Free House

Hardwood floors and leather banquettes imbue this casual neighborhood bar with warmth and sophistication. It’s as much the spot for craft cocktails as it is for cheap beers. The food menu offers bar snacks, charcuterie, salads, and meat-forward dinner items. Partially covered patio seating is available for those wanting an airy atmosphere. 

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.

Round tables are lit by globe light fixtures within Andina’s private dining room. Alyson Levy/Andina

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. 

Angel Face

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. 

Hey Love

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.

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.

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 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 set a tone for the amorously inclined.

The Richmond Bar

This down-to-earth bar is the ideal setting for a casual date. Slide into a booth and let the laid-back environment calm the first date jitters. Richmond boasts a variety of aptly named cocktails, as well as a beer and wine menu. From shoestring fries to a meat pie with wild boar and veggies, the food menu is unassuming but enticing. Prefer outdoor seating? Richmond offers a heated patio out back, complete with a fire pit. 

Lauren Massie/The Richmond Bar

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Someday

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. 

A paved alleyway in between two buildings, one pink and one painted with a mural, with Christmas lights criss-crossing across the two buildings.
The alleyway leading to Someday.
Dina Avila/EPDX

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