Date Night PDX

25 Great Dates in and around Portland

Romantic evenings, chill times with a pal, roving parties, and trips for two: plan your next outing or overnight here.

Edited by Eden Dawn By Hannah Bonnie, Kelly Clarke, Ramona DeNies, Zach Dundas, Rebecca Jacobson, Fiona McCann, Marty Patail, Anya Rehon, Margaret Seiler, Benjamin Tepler, and Eleanor Van Buren January 30, 2018 Published in the February 2018 issue of Portland Monthly

Romantic Dates

These pheromone-rich outings are the equivalent of a Sade song.

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Image: Meg Hunt 

Dance Your Troubles Away

Saturday nights at Clyde’s Prime Rib—the Northeast Sandy steak house that’s shrugged its shoulders at New Portland since 1955—is something to behold: a live band turned up to 11 cranking out Daft Punk covers and soul classics with furious energy; couples and singles dressed to the nines, dancing shoulder to shoulder with pre-Trumpian abandon. Martinis and beers and steak bites miraculously appear from behind a sea of heads at the bar, where the real estate is more valuable than anything on Division. Make reservations in the restaurant for the eponymous prime rib, get dressed up (no fleece whatsoever; put on a goddamn suit!), and then head to the bar at some point after your second round of manhattans, or when the thumping music starts to lure you in. The crowd skews older in the best possible way. Let the youth self-consciously sip cocktails in some converted industrial garage. Hit up Clyde’s when you’re old enough to party. —MP

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Pretend You’re in Europe

Garden lovers Burl and Cindy Mostul bought an old hayfield in Canby in 2004 and lovingly turned it into something straight from the Pyrenees. Now the expansive estate, Villa Catalana Cellars, boasts a home modeled after San Clemente de Tahull, a 12th-century Romanesque church in Catalonia. Get a glass of wine inside the stunning greenhouse before walking among acres of ponds and rare-to-here plants: eucalyptus, Italian cypress, citrus, and olive trees. Not enough cute? Tiny farm kittens occasionally poke their heads up while frolicking in the gardens. It’s all a vintage foreign film come to life. —ED

Take a Fancy Wander through Northwest

The classically urbane quadrant makes a lovely setting for a pleasantly aimless evening. Happy hour at Paley’s Place offers bites of stone-cold-classic Northwest cooking at less than $10 per shareable small plate. (On a recent visit, the bartender confided that the humble French fries are his favorite. We concur.) A postprandial ramble among the lively storefronts and artfully aging apartments on and between 21st and 23rd Avenues can culminate in a glass of something nice at M Bar, possibly the smallest, and just maybe the most romantic, tavern in town. —HB & ZD

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Angel, Baby

Don’t underestimate the classic combo of drinks and a flick. Start at intimate east-side bar Angel Face, with its delicate candlelight and famous faux wallpaper. Give the bartender your preferred spirit and then just trust before making your way across the street to the historic Laurelhurst Theater. This cinema-meets-pub showcases $4 second-run movies and an array of independent and classic films. Things going well? Cross the street and share a cone of Tahitian vanilla at Fifty Licks. —AR

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Sweat Together

At the Finnish-inspired sauna Löyly, duos can don swimsuits (same-sex pairs have a naked option on certain days) for a little evening unwinding, a midday escape, or some morning-after detox before wandering to a nearby brunch at Tasty N Sons or La Panza. The Southeast location has a more social feel, while the NE MLK Löyly designates one of its two cedar saunas as silent, if you just want to gaze into each other’s eyes—until the sweat drips off your forehead and you have to blink. —MS

Group Dates

For the cavalcade of couples

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Image: Meg Hunt

L8ter Sk8ter

There are few times in life to share shoes. This is one. Lace up for the 9:30 p.m. adult late-skate session at Oaks Park on Tuesday nights. Amass your friends (and their friends, whom you seek to know better) and boogie at one of the largest rinks in the country as a DJ spins live music. Impress that cutie in your group with your aerodynamism and your penchant for cotton candy and ’80s lyrics. Or, as you slowly get up from the waxed wooden floor, declare exasperatedly, “I keep falling for you.” —EVB

Bingo, Boingo

It’s one of the easiest possible games to play while downing a drink. And you can win some serious cash if you (literally) play your cards right. The question is, what kind of vibe are you into? The Monday-night Spare Room Bingo is a low-key classic, with a blackout prize worth as much as $700 (!)—which could buy you approximately 87 of the bar’s Fiery Ginger cocktails (Kahlúa, Baileys, Fireball, and Jameson). Or there’s the glitter route: McMenamins’ Drag Queen Bingo show, hosted by one of the funniest babes in the whole city, Poison Waters. —ED

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Sing. Sing a Song.

Spacious karaoke spots like the various Chopsticks locations give a large group room to move (and dance), while the setup at tiki haven the Alibi or Baby Ketten’s weekly spots (currently Century and Alberta Street Pub) are more comfortable for smaller crews. Want the place to yourself? Book a private suite at Voicebox. Pro tip for the latter: hop on the Tuesday-night flat-rate special for groups of seven or more, and avoid end-of-the-night haggling over who pays what. —MS

A Night of Knives & Fire

“You like fire?” With those words, the chef behind a flat-top grill ringed with eight seats ignites a huge plume of flame, kicking off a procession of knife tricks and edible dinner theater. This is Tokio Table, the inner east side’s locally owned version of Japanese teppanyaki chain Benihana.* Cooler interactive food experiences (hot pot to Korean barbecue) have supplanted teppanyaki’s live-chopped dinners over the years. But for throwback fun, few things beat a crowded grill and steam-billowing volcanoes built out of onion rings. Watching a chef spell “I ❤ you” in mounds of fried rice is the great equalizer: first-daters, grandparents, and middle school soccer teams all love it. The portions are large and Americanized, and everything tastes like garlic butter. —KC

*We’ve still got one of those in Beaverton; it’s exactly like you remember it.

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Get Out

You’re an FBI cadet about to enter an assassin’s lair. Or maybe you’ve been charged with treason by the British Empire and have one hour to get away from the firing squad outside your tent. Or it could even be a good old-fashioned zombie apocalypse. The newest craze of team togetherness is all about escape rooms—Escape Games PDX, Hour to Midnight, and Portland Escape Rooms, to name a few—where a group of lovers/friends/early-daters must work together to solve hidden clues in a locked room to prevent any number of certain dooms that await. —ED

Overnight Dates

Some adventures need at least 24 hours.

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Image: Meg Hunt

Trailer Cuddles

After a pit stop in Astoria to comb the vintage shops, head to Long Beach, Washington, and share risotto, wild mushrooms, and wine at the Pickled Fish restaurant from an ocean-view seat while a live band belts out Journey songs feet away. Afterward, check into one of the many funky vintage trailers at the Sou’wester Lodge, perfect for listening to records and laughing in a tiny living room before falling asleep to the sound of rain plinking on the tin roof (an IRL white-noise app). —ED

I Choo-Choo-Choose You

Let’s just keep in mind, first of all, that the rail link between Portland and Seattle has been a vital and successful part of the Northwest for years, December’s tragic derailment notwithstanding. A pair of tickets on the Coast Starlight (with its old-school observation car) and a bottle of wine to split as eye-popping views roll by is a legit PNW date. Hit Seattle Art Museum, the Rem Koolhaas–designed library, or the iconic Pike Place Market, which is one of those super-touristy destinations that remains really cool. For lodging, look into a classic-classic at the nearby Edgewater Hotel, built for the 1962 World’s Fair and once shelter to the Beatles, or a mod-classic at the original Ace, the haute-minimalist den that launched a thousand boutique hotel concepts. —ZD

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It’s Wheeler Time

Tucked into a fold of Nehalem Bay, the little town of Wheeler (yes, founded by forebears of Portland’s mayor) is the Oregon coast equivalent of an intimate moment. Make home base a yurt at Nehalem Bay State Park, or ensconce yourself in Roaring ’20s plushness at the restored Old Wheeler Hotel. Hit Wheeler Station Antiques for some A+ browsing, or stroll down to Waterfront Park. Scheduled for a March opening, the brand-new Salmonberry Saloon promises music to pair with stiff drinks, smoky salmon chowder, and bayfront sunsets. —RD

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Sexy Staycation

Dim lights, a swooping curved bar, Champagne cocktails, wood-paneled walls, and a frozen-in-time midcentury ambience mark the Hotel deLuxe’s Driftwood Room as the stuff of date-night dreams. If Reese Witherspoon can find herself a one-night hook-up with a stranger here (see Wild for details), then what’s to stop the rest of us? If all goes to plan, get a room! Complete your saucy staycation (or sleep it all off) on the eight-foot circular (!) bed in the Marlene Dietrich Suite. —FM

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Be Edgy

Here’s the deal with McMenamins Edgefield, a restored 107-year-old poor farm: it’s full of dates. So many, it’s best to just get a room and do it all. Start with a round of par-3 golf before burgers in the Black Rabbit courtyard. Then take a walking tour of the gardens, or sit in a porch rocker with a glass of wine. Next, decide between darts, pool, or a movie in the on-site theater. Wrap up the evening in the steamy saltwater soaking tub, full of little swimming channels and snuggly spots. —ED

Funtivity Dates

Whether you’re on date no. 1 or a few hundred into the relationship, a kick-ass activity makes everyone feel at ease.

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Image: Meg Hunt

Island Vibes

Beach day without the long drive? Hell, yes. Head to Sauvie Island, the half-wildlife-refuge, half-rural-farming community 10 miles northwest of town. There are famous (some, clothing-optional) beaches to lounge on as big boats go by. Hit a farm stand for fresh snacks and picnic alongside the lush Wapato Access Greenway trail. Then head over to one of the most Instagrammable nurseries around, Cistus, home to heavenly greenhouses and themed areas with yucca plants the size of a Car2Go. —AR

Show Your Smarts

Personal anecdote: In my moonlighting gig as a bar trivia* host, I’ve watched strangers become friends, and friends become something more, bonding over a shared knowledge of William Wyler movies or ’90s slow jams. “It’s a great way to not have to awkwardly converse about nothing as you get to know each other,” says Rose Thor, who met her now-partner, Ric, when they joined mutual friends on a team one night. You can also show off a bit, she adds: “Ric says that he was impressed by me knowing the entire taxonomic classification of a human being. He blew me away with his geography knowledge.” —MS

*Local trivia purveyors include the Bar Exam, Quizissippi, Quizzy, Rain Brain, and ShanRock’s Triviology (disclosure: I’m a ShanRock trivia jockey, or TJ); Portland also has numerous locations of national trivia outlets like Geeks Who Drink and Last Call.

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Go Chasing Waterfalls

During the summer, Silver Falls State Park—which boasts 10 gushing cascades—teems with hikers. Go in the off-season for thinner crowds and more cuddleportunities in the grottos hidden behind several of the waterfalls. (Or find, ahem, inspiration at tiny Frenchie Falls.) The full loop clocks in at 8.7 miles—though it’s easy to turn back early—with most of the trail wide enough for side-by-side strolling. Afterward, warm up with soup, sandwiches, and suds in nearby Silverton’s cute MillTown Pub. If there’s even an ounce of sun, sit in the garden. —RJ

Get Square

This may sound like an awkward time your quasi-celibate great-grands had before the Old Grange burned down and Monsanto bought them out. It’s not that. The Every Wednesday Square Dance, stomped on the floorboards of NE Dekum’s Village Ballroom, breathes fresh life into a great American folk art. Local string bands provide the music as callers prompt a diverse crowd through the form’s many variations. Big surprise? Square dancing turns out to be kinda ... sexy. You swing your partner, and then you swing the next partner. (The atmosphere is respectful and supportive.) In a Portland dance, of course, anyone can fulfill the roles of gent or lady—and one session a month is officially gender-neutral. —ZD

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Sail Away, Sail Away, Sail Away

One of the quickest ways to bond might be tackling a task together. Hop on one of Scovare Expeditions' sailing lessons and learn how to helm each other’s jib, if you know what I mean. You’ll get the basics from your instructor, then take the wheel and run up and down the Willamette with the wind in your sails, making daydreams of running away together for #boatlife feel possible. —ED

Friend Dates

Your bestie deserves face-time, too.

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Image: Meg Hunt 

Party in the USSR

When throwing a Russian dinner party, it’s best to follow the generations-old advice of Southeast Portland’s Kachka: 1. Never Drink Alone. 2. Always Drink for a Reason. 3. Never Drink Without Eating. Basically, throw a pelmeni dumpling-making party with lots of infused vodka, from crowd-pleasing horseradish to a truly Russian Moscow mule infused with lime. For more sage wisdom—including fail-safe toasts and how to Tetris your table full of zakuski (drinking food)—nab of copy of the restaurant’s recently published cookbook, Kachka: A Return to Russian Cooking. —BT

Float to Margaritaville

This is a plan that requires good weather, but it’s worth the wait. First stop is Alder Creek Kayak & Canoe rentals at Jantzen Beach. Get your preferred method of floaty thing, then paddle your way out onto the Columbia as vitamin D floods your bodies. After you’ve worked up an appetite, you can pull straight up to the dock at the can’t-believe-this-exists-in-Oregon Island Café and hop out onto the floating bar where, among the strains of “Kokomo,” mai tais and fish tacos await. —ED

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2 for 1

Weekend dates are so limiting. Living Room Theaters does two-for-one admission on Monday and Tuesday nights in their comfy, preassigned seats. Since you’ve saved, head across the street to Clyde Common and try its standout Southbound Suarez: tequila with house-made horchata. Can’t wait for movie popcorn? Clyde’s killer version—togarashi, honey, and butter—can surely satisfy your salt fix. —EVB

Shop Hop

Looking for a new lover love seat? Spend a day crawling Hawthorne for midcentury-modern gems at the likes of Hawthorne Vintage Modern or Red Snapper. Stop into the classic Space Room for a cocktail underneath planetary murals before you continue down the strip and comb the multivendor masterpiece House of Vintage. Finish off the day with a healthy feast at the vegan queendom Harlow. —EVB 

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Happy Feet

“I just want to spend time with you,” your mom/best pal/snuggle partner says. Great! Catch up while receiving side-by-side foot massages on a cushy purple couch and sipping good tea in a tranquil, Cost Plus World Market-y relaxation chamber at Barefoot Sage. The foot-centric spa’s $25 signature soak nets you a half-hour treatment: toes swimming in a bowl full of steaming, rose petal-strewn water; stress nowhere to be found. —KC

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