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Kids, this is the story of how I met your mother, and it was all thanks to PDXtoday.
OK, so maybe that’s not exactly how the 2000s sitcom went, but if Ted Mosby had consulted us for date night ideas, we could’ve shaved the show down to two seasons (and saved his kids a lot of time). Regardless — whether you’ve met “the one” or are hoping to impress someone new, we’ve got 45+ local date night ideas that are legen — wait for it — dary.
Evening and brunch shows are scheduled every weekend at Darcelle XV Showplace.
Photo by Another Believer
For the ones who want a night out on the town
- Live it up at the longest-running drag cabaret on the West Coast, Darcelle XV Showplace, founded by the late Walter Cole.
- Descend into the Jack London Revue — a small hideaway jazz club that hosts world-class musicians.
- Move your feet and spend some dynamic time with your partner at Southeast Portland nightclub, Holocene.
- Step into The Coffin Club for a concert, burlesque show, or tarot reading surrounded by gothic decor.
- Head to a renovated former church — Mississippi Studios — for an intimate live music experience.
- See your date in a new, psychedelic light at the indoor, all-ages playground/immersive art experience Hopscotch.
If the way to their heart is through their stomach
- Does your significant other love bagels? Could they eat pasta for breakfast, lunch, and dinner? Learn to make their favorite food by taking a class at Cookshop.
- Nosh on farm-to-table European small plates at Navarre.
- Set love ablaze with a flaming scorpion bowl at tropical-themed dive, The Alibi Tiki Lounge.
- Pedal your way around Portland’s craft beer scene with a BrewCycle ride.
- Get a scoop of New Zealand-style ice cream at Nico’s Ice Cream, or skip the line of tourists at Salt & Straw by picking up a pint to go. Grab a couple of sampling spoons so you can enjoy it together while sitting on a bench.
- Take the relationship to new heights at The Hoxton’s trendy rooftop bar, Tope.
- Get cozy and sip a glass of wine in a candlelit nook at M Bar.
- Sit under the pale silk petals of a decorative cherry tree while eating Japanese-Korean fusion dishes at Janken.
- Show off your knowledge of trendy local restaurants with equally fresh menus + drinks at G-Love, or its sister bar, The Love Shack. Their names alone will win hearts.
- Bond over sourdough pizzas and scratch-made limeade under the lantern-lit, grape-vine-covered patio at The Turning Peel.
If you love the great outdoors
- Choose your adventure with a hike in Forest Park, one of the largest urban forests in the United States.
- Spread out a picnic blanket, bring some snacks, and watch a sunset at Skidmore Bluffs.
- Stroll beneath massive, concrete arches and take a self-guided tour of the resident trees at Cathedral Park.
- Need a subtle excuse to spend time with a crush? Get your canine companions together for a play date at a dog park.
- Quote Shakespeare while strolling through fragrant blooms at the International Rose Test Garden or Peninsula Park Rose Garden.
- Get to know the other person at their sweatiest with a PDXtoday Hike of the Month.
- Learn about your date’s artistic tastes with a self-guided stroll along the Portland Street Art Loop Hike.
- Get to know your date and the plants living near you with an urban foraging class from Rewild Portland.
For the ones who like to play games (just not with your heart)
- Test your competitive compatibility with an evening of pub trivia. Try Untapped Trivia, which supports Family Dogs New Life Animal Shelter.
- At Portland Axe Throwing, you can demonstrate your usefulness in a zombie apocalypse by hucking weapons at wooden targets while holding an IPA in the other hand.
- Show your shared love for a local sports team at a home game for the Trail Blazers, Timbers, Thorns, or Pickles, to name a few.
- Bring your appetite and a board game to Mox Boarding House. You can also borrow a game from the restaurant’s library, or buy a brand-new one from the shop attached to the restaurant.
- Up for some friendly, 8-bit competition? Pocket a bottle of hand sanitizer and indulge in vintage video gaming at Ground Kontrol or Next Level Pinball Museum.
If you’re really hoping that it works out
- Show off your ability to plan ahead by snagging a hard-to-get reservation at Kann, aka America’s “Best New Restaurant.”
- Watch Portland’s famed — and free — avian show as thousands of migrating Vaux’s swifts make their annual stop at Chapman Elementary School. With so many birds, the odds of getting pooped on are high… and some consider that a sign of good fortune.
- You and your date won’t want to jump ship after spending time together on the river. Book a sailing adventure or rent a kayak, Jet Ski, pontoon boat, and more through GetMyBoat.
- Find out what falling (in love) really feels like by mastering the wind tunnels at iFLY Indoor Skydiving.
- Plan a picnic — or let professionals plan one for you.
- Get crafty together at Creative Culture, a DIY craft studio loaded with fun ways to pass an hour or two. If that’s not enough to tempt you into an artsy undertaking, know that you can also order milkshakes topped with whole slices of cheesecake.
- Enjoy some TLC together by getting a couple’s facial at The Jungle Room, the hidden spa in the back of plant and wellness business BOSK.
If you want an “old fashioned”-style date
- Take your significant other out for dinner and a movie at one of Portland’s independent dinner and beer theaters, like the iconic Hollywood Theatre, the artsy Laurelhurst Theater, Living Room Theaters (which is 21+ in the evening), or the historic Clinton Street Theater.
- Bask in the retro nostalgia at Stepping Stone Cafe, which started as a soda fountain in the 1940s.
- Buckle up and head to 99W Drive-in Theater in Newberg for a double feature from the comfort of your car.
- Pretend you’re in a Hallmark movie by going ice skating any time of the year at Lloyd Center Ice Rink.
If fall always makes you fall in love
- Plan a tour of Portland’s unbe-leaf-ably beautiful fall foliage hotspots. The leaves are dead but the chemistry won’t be.
- Wander through neighborhoods that are particularly magnificent during autumn, like Goose Hollow and Nob Hill, leaving time to pop into shops and restaurants.
- Pick pumpkins at a local farm to carve and decorate together. You can learn so much about a person from their jack-o'-lantern choices.
- Take a drive through the Hood River Fruit Loop, where you’ll find a bushel of orchards offering u-pick apples.
- Get lost in a corn maze and find out who has the better sense of direction (aka self-preservation escape skills).
- Step into an alternate Halloween-themed reality circa the late 1990s with a trip to Halloweentown.
- Discover a shared appreciation for unique spectacles at the West Coast Giant Pumpkin Regatta.
If you wanna show off by knowing all the hottest events in town
- Shameless plug: Sign up for our daily newsletter, where we call out our top picks of things to do around town. Your date doesn’t have to know we’re behind it, you can take all the credit.
- Stay up-to-date on the coolest local events around Portland with our events page (and check out this guide for our tips on navigating the page).
What did we miss? If you know a perfect date spot that’s not on the list, point us in the right direction.
