24 Great Portland Date Ideas You Can Do Right Now

Portland can be a daunting city to date in, especially when the rainy months start up and no one wants to go outside, let alone meet up. That said, we've been experiencing an influx of new residents like never before over the past couple of years, and with dating apps, websites, and friends of friends of a coworker, there’s always some opportunity to meet someone new.

Getting someone to agree to go out with you is on you. But once you do, we have a plethora of options for great dates around town, even ones that won’t be too hard on the wallet and won’t have you ending up at Applebee’s or a loud, rowdy sports bar (though we love a good dive as a date spot). And if you don’t see anything that you love here, be sure to take a gander at our locals-approved list of super fun things to do around Portland for some more ideas.

Grab dinner at a food cart pod

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A huge aspect of Portland’s culinary scene is the amazing food cart options around town. Every neighborhood has at least one and most of the time they’re organized into pods. This means even if you and your date have drastically different tastes in food, you can still both find something. Many pods even have covered areas for the rainy months, and even nearby taphouses to bring your food into.

Snag cheap drinks at happy hour

Multiple, multiple locations
It’s the quintessential first date move for a reason. It’s low investment, involves drinking, and you or your date can bail when happy hour is over without it being too awkward or late. Almost every bar and restaurant in town offers some kind of happy hour, but the best moves are the $3 cocktails at the modernist Aalto Lounge, boozy mason jars at Swift Lounge, $6 craft drinks at the rustic Rambler, or discounted champagne cocktails and snacks at the dark, intimate Driftwood Room. You could also say screw it and hit up one of our infamous dive bars to keep the good times rollin’.

Go classic and sip on a latte

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Not everyone drinks, and not everyone has time for an evening date. Enter one of the world’s most popular first date options: grabbing a hot, caffeinated drink at one of our many, many cafes, coffee shops, and tea shops around town. The chic, minimalist chain Tea Bar makes hot tea and matcha lattes, Barista employs some of the best latte artists in town, and Never Coffee steams up some unique latte flavors, like the Oregon with hops, dulce de leche, and Jacobsen Salt.

Head out on a beer tour

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Portland is famous for being a sudsy city for a very good reason. Besides the sheer number of breweries we have, we all also have a plethora of fantastic tap rooms, beer festivals, tours, and brewpubs. Go out on a structured tour, hit up a festival, or build your own beer crawl.

Take a hike in Forest Park

Forest Park
We’ve got the largest parks (within the city limits) in the country, so why not take advantage with a leisurely stroll, a woodland run, or a hike? Seriously, Forest Park covers around 5,157 acres with 80 miles of trails. The thick canopy of trees keeps the area relatively dry during the gray, rainy months. Besides, you can’t be a true Portlander without a good surplus rain jackets.

Get cozy at the Living Room Theater

Portland is teeming with top-notch beer theaters in cool neighborhoods, with Living Room Theater being located in the boozy West End area that’s not quite The Pearl and not quite Downtown. Admission is only $6 on Mondays and Tuesdays at this spot (except on holidays), which features plush seats for getting extra cozy.

Catch some cheap -- or free -- stand-up

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There’s plenty of stand-up comedy in this town, and much of it is surprisingly good. Some of it is free, like It’s Gonna Be Okay, every Monday night at East Burn, which features both professional and amateur stand-up comics, all of whom have been well-vetted to avoid any so-called “edgy” comedians. Other places, like Helium Club and Harvey’s Comedy Club often have tickets as low as $10 with some seriously talented comedians. However, take a date to an open mic night strictly at your own risk.

Make your own pancakes at Slappy Cakes

Pancakes rule. Especially when you’re making your own inventions on a hot griddle with a Bloody Mary at your side. You can choose from five batters, a laundry list of fixins, and toppings like goat cheese, caramel spread, and syrup, of course.

Head to OMSI After Dark

Central Eastside
Go drinking and get a healthy dose of science with OMSI After Dark, a 21+ event that offers fun specials like a bourbon and bacon night. The museum's exhibits will also be available to explore and play around in… with no children in sight!

Drink flaming coffee drinks at Huber’s

Fun fact: The Spanish Coffee is not, in fact, from Spain, but rather from this vintage Portland restaurant. They’re $12.50 a mug, but they’re also filled with Bacardi 151. It’s worth it alone for the ice-breaking pyrotechnics as they literally will light your drink on fire.

Go on a saucy spirits tour 

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This is not the haunted locations tours -- we mean boozy spirits. Portland is home to an amazing number of distilleries, and most of them offer tasting flights at affordable rates. That way you can get pretty sauced up without all the guilt; it’s an experience, plus you’ll be supporting local businesses. Grab a passport and have a ready excuse for a second and third date as you fill in the ones you missed before.

Visit an urban winery

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Heading out of town to wine country is a classic Portland move, but it also takes an hour of driving, and then you’re forced to drive back home after consuming what is likely an unsafe amount of wine. Instead, head to one of our many urban wineries like Southeast Wine Collective, Teutonic Winery, or Enso Winery to sample the bounty of Oregon’s wines while still being able to get a Lyft home for less than $200.

Catch a Sunday Session at Rontoms

During the fall and winter, Rontoms’ Sunday Sessions move inside where it’s not soaking wet. The weekly night of free music offers the perfect low-stakes opportunity to check out up-and-coming local bands and impress your date with your adventurous taste in music in the process. Granted, if the band does not, in fact, slap, that’s on you. Just tell your date that they used to be a lot better.

Day trip to the coast

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Once you’re there you can check out the sites in towns like Seaside and Cannon Beach. This is obviously a third or fourth date thing. No one wants to go on a long drive with a stranger.

Enjoy Costco dogs, soda, and airplanes

Grab your Costco card (you do have one, no?) and take your lucky date for some sausages and fountain drinks. Romantic, right? After, make a short jaunt to Marine Drive and watch the planes take off from PDX. Bonus points if you can actually impress your date with your best Wayne’s World impression. It’s not cheap -- it’s “Old-School Portland”.

Play B-movie bingo at the Hollywood Theater

The first Tuesday of every month is like your own semi-private episode of Mystery Science Theater 3000 at the Hollywood, only the characters of god-awful dollar-bin fodder like Ninja 3: The Domination actually show up to confront their shoddy resume in real life. Plus, the movie theater has pizza, beer, and cider.

Check out the Portland Bucket List and tick off a box or two

All over Portland
Finding fun things to do is deceptively difficult -- even in a bustling city like this one. So we found 59 things you absolutely must do before you die (or move!) and are leaving the rest up to you. 

Blue Star Donuts
Blue Star Donuts

Hang out at PDX... seriously!

The airport which the city gets its handle from, Portland International Airport actually has some great dining, including The Country Cat, Blue Star Donuts, Tamale Boy, and Laurelwood, and it makes for some of the best people watching in town. And hey, if the date is going atrociously, you can always excuse yourself and fly far far away from here.

Play some free video games at Ground Kontrol 

On the second Thursday and last Wednesday of every month Ground Kontrol puts its games on free play and charges a $7 cover, so you can finally beat that last level of Double Dragon with your date without breaking the bank. Then, you can spend the rest of your budget on cheap drinks and even cheaper hot-dogs, although it’s better to head a block away for tacos and tequila at Mi Mero Mole.

Try Powell's and pizza

Flip through some books together in the Rare Book Room at Powell’s Books, or just wander the stacks together. Then, head across the street to Sizzle Pie for a slice and a drink. Just don’t do it in reverse order -- the staff at Powell’s frowns on getting grease stains all over the rare books.

Test your brain-smarts at Geeks Who Drink

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You can find a Geeks Who Drink trivia night every night at the week, hosted at various bars all across town. You’ll be able to impress your date with your brilliant knowledge of state capitals and facts about the show Airwolf (1984-1987), and all it will cost is the price of whatever drinks you feel will enhance your trivia skills.

Grab a Coquine cookie and hit the trails

Mount Tabor
It may seem like it, but it doesn’t actually rain all the time in Portland. There are plenty of dry days that award you the opportunity for a jaunt in the park. The best way: head to Coquine, grab one of their stupidly good chocolate chip cookies along with a cup of coffee or two, and go for a walk on the country’s only active volcano in a city limit: Mount Tabor.

Share a Pot of Tea at Townshend's

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One of Portland’s best teahouses, Townshend’s Tea offers a staggering array of sustainably sourced teas from China, Japan, India, and more. It’s a low-pressure environment that allows you to sip some teas and discuss French cinema, Japanese literature, German prog-rock, or whatever else you lied about liking on your OKCupid account.

Support our local artists

First Thursday is a time-honored tradition, when galleries in Northwest throw their doors open for everyone to tour. You can bond over a discussion on the juxtaposition of the human form with modern industrialism and capitalism, as depicted in the medium of recycled PBR cans and power cables. It’s sexy. Plus, they generally have free wine and beer at all the galleries. Skip the hoity-toity Pearl galleries and stick with the much cooler Old Town/Chinatown ones.

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Alex Frane has pretty much hit every one of these date options in some form or another at some point. Follow him (or slide into his DMs if you wanna take him out to one of these) at @franiacdrinks.