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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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Note: Restaurants on this map are listed geographically.

1. The Bye and Bye

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1011 NE Alberta St
Portland, OR 97211
(503) 281-0537
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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.

2. The Box Social

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3971 N Williams Ave
Portland, OR 97227
(503) 288-1111
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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.

3. Wonderly

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4727 NE Fremont St
Portland, OR 97213
(503) 288 4520
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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.

4. Liberty Glass

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938 N Cook St
Portland, OR 97227
(503) 517-9931
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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.

5. Secret Society

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116 NE Russell St
Portland, OR 97212
(503) 493-3600
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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.

6. Picnic PDX

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1305 NW 23rd Ave
Portland, OR 97210
(503) 719-7768
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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.

7. Andina

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1314 NW Glisan St
Portland, OR 97209
(503) 228-9535
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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.

8. Pope House Bourbon Lounge

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2075 NW Glisan St
Portland, OR 97209
(503) 222-1056
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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.

9. Tope

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15 NW 4th Ave
Portland, OR 97209
(503) 770-0500
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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. 

10. The Observatory

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8115 SE Stark St
Portland, OR 97215
(503) 445-6284
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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.

11. Departure

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525 SW Morrison St
Portland, OR 97204
(503) 802-5370
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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.

12. Punch Bowl Social

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340 SW Morrison St Fl Rotunda
Portland, OR 97204
(503) 334-0360
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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.

13. The Pied Cow

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3244 SE Belmont St
Portland, OR 97214
(503) 230-4866
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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.

14. A Roadside Attraction

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1000 SE 12th Ave
Portland, OR 97214
(503) 233-0743

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.

15. Sapphire Hotel

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5008 SE Hawthorne Blvd
Portland, OR 97215
(503) 232-6333
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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.

16. Bible Club

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6716 SE 16th Ave
Portland, OR 97202
(971) 279-2198
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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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1. The Bye and Bye

1011 NE Alberta St, Portland, OR 97211

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.

1011 NE Alberta St
Portland, OR 97211

2. The Box Social

3971 N Williams Ave, Portland, OR 97227

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.

3971 N Williams Ave
Portland, OR 97227

3. Wonderly

4727 NE Fremont St, Portland, OR 97213

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.

4727 NE Fremont St
Portland, OR 97213

4. Liberty Glass

938 N Cook St, Portland, OR 97227

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.

938 N Cook St
Portland, OR 97227

5. Secret Society

116 NE Russell St, Portland, OR 97212

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.

116 NE Russell St
Portland, OR 97212

6. Picnic PDX

1305 NW 23rd Ave, Portland, OR 97210

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.

1305 NW 23rd Ave
Portland, OR 97210

7. Andina

1314 NW Glisan St, Portland, OR 97209

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.

1314 NW Glisan St
Portland, OR 97209

8. Pope House Bourbon Lounge

2075 NW Glisan St, Portland, OR 97209

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.

2075 NW Glisan St
Portland, OR 97209

9. Tope

15 NW 4th Ave, Portland, OR 97209

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. 

15 NW 4th Ave
Portland, OR 97209

10. The Observatory

8115 SE Stark St, Portland, OR 97215

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.

8115 SE Stark St
Portland, OR 97215

11. Departure

525 SW Morrison St, Portland, OR 97204

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.

525 SW Morrison St
Portland, OR 97204

12. Punch Bowl Social

340 SW Morrison St Fl Rotunda, Portland, OR 97204

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.

340 SW Morrison St Fl Rotunda
Portland, OR 97204

13. The Pied Cow

3244 SE Belmont St, Portland, OR 97214

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.

3244 SE Belmont St
Portland, OR 97214

14. A Roadside Attraction

1000 SE 12th Ave, Portland, OR 97214

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.

1000 SE 12th Ave
Portland, OR 97214

15. Sapphire Hotel

5008 SE Hawthorne Blvd, Portland, OR 97215

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.

5008 SE Hawthorne Blvd
Portland, OR 97215

Related Maps

16. Bible Club

6716 SE 16th Ave, Portland, OR 97202

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. 

6716 SE 16th Ave
Portland, OR 97202

Related Maps