THE FIRST CHALLENGE to any good date is for both people to snap out of their beleaguered work state-of-mind and realize, dear God, they are supposed to be behaving in a romantic fashion. This sensation tends to dry up a conversation almost immediately, as each person slings enough mundane “tell me about yourself” questions to distract from the growing sweat stains in their armpits, the insecurity about where to put their hands, and the rambunctious belly sounds that might lead someone to believe they are hiding another person inside themselves.

This is why you need to show up to every date with a plan. At the very least, your game plan will give you a list of things to rattle off to your date to sound interesting, cultured. A real catch. Fortunately, Portland, Oregon, has plenty of options to cram on that list.

Casual Lunch

Maybe you aren’t quite ready for a “date-date” involving candlelit dinner and figuring out how close they are to their mom, so why not go for a more casual approach by visiting Hawthorne, Portland’s original “keeping it weird” district?

Start your date with lunch at the food carts at Hawthorne and SE 12th (Perierra Creperie never disappoints) before some window-shopping at Vintage Pink, and true vintage shopping at Buffalo Exchange, The House of Vintage, and The Red Light. Exiled Records and Jackpot Records are stellar if you are looking to find out your date’s music tastes. If you are really trying to show off your Portland cred, don’t forget to peruse the collection of bongs (ahem, water-pipes) at Nomad Crossing, or go all out and get a tattoo at Hawthorne Ink.

Still have your date’s attention? Cool off with a beer at the Spaceroom Lounge or head to the Backstage Bar of the Bagdad Theatre before hitting up a matinee screening of a cult classic indie flick.

Outdoor / Alternative

In the heat of summer, one of the best possible dates (i.e. fairly committing) is tubing down to the Clackamas (at Barton Park) or the Sandy (at Oxbow Park) rivers. If you are feeling even more adventurous, you could try one of the Columbia Gorge hikes like Eagle Creek or Horsetail Falls, which are as beautiful as they are convenient for making conversation out of the types of birds and flowers you come across.

Trying to stay closer to downtown? The walking trails between the Japanese Garden and the Oregon Zoo in the Hoyt Arboretum are packed with views of a city surrounded by lush forest. If you are looking for a moonlit view of the city, the best nighttime lookout can be found at Pittock Mansion.

Brewpubs and Grub

A good date night in Portland almost always kicks off with a few pints of one of our local brews.

Downtown’s DeschutesRogue and Bridgeport breweries are standards that match the highest quality pub grub with a more easygoing setting, and you won’t find better beer anywhere else. 10 Barrel is an up-and-comer on the scene with a rooftop bar and some killer views of the city. Kells and Widmer Brothers have been beloved by locals for decades, with the former offering live folk and rock music while the latter boasting the best beer garden in the city. All of these beer-lover heartthrobs are within walking distance of downtown (or a short cab ride).

Game Night

The getting-to-know-ya phase is never easy and beer can only help you so much, which is why you should feel free to rely on Portland’s array of gaming venues for breaking the ice.

After a few pints of lager at Kells or a toasted hefeweizen at Widmer, hit up downtown’s Glowing Greens for glow-in-the-dark putt-putt golf (even cooler than it sounds). Other gaming spots include Pips and Bounce for Ping Pong, the Rialto for billiards, and arcade games at Ground Kontrol. Save Glowing Greens, each of these spots double as fantastic bars.

If you are looking to do something truly bold, there is a growing escape room scene in Portland, including Escape Games PDXLabyrinth Escape GamesHour To Midnight and 60 Minutes to Escape. No better way to get to know someone than via human-sized mind puzzles.

Sophisticated and Sexy

The heart of Downtown’s “Cultural District”, SW 9th is where you go for something a bit on the classy side (maybe break out your fancy clothes). Start with a quick visit to either the Portland Art Museum or, if they are an out-of-towner in need of some local schooling, the Oregon Historical Society. Make sure you point out the gleaming white and red spire of the First Congregational Church while walking through the historic South Park Blocks.

If you two are getting along well, head over to either Shigezo or Ringside Fish House for two of the best downtown Happy Hour spots (both operate between 4-6PM). After that, walk down to SW Stark for fancy crawfish dinner at Jake’s or a more subdued couple of bocadillo sandwiches at Pepe Le Moko. Follow up with a digestif cocktail at the Multnomah Whiskey Library before some dancing at Lola’s Room. Polish it all off with a casual romantic stroll between the mystery novel aisles at Powell’s City of Books. Maybe even go for a smooch in the rare book room.

The Night Cap

Photo: Circa33

So it’s getting late and your date hasn’t bolted. Well done. You could end the night here, after getting smoked at putt-putt and showing off your knowledge of non-fiction authors, or you could throw in for one more date-night staple to seal the deal.

On a quiet corner near the commercial edge of Division Street, not only does Victory Bar have an atmosphere to die for, but it also plays music almost exclusively from the 1970’s. Not a bad spot for rum cocktails and some over-the-top ballads from Queen, Elton John and Paul McCartney. If you really want to feel exclusive, head over to Circa 33, which you enter through a bookcase via password, and order cocktails straight out of the prohibition era. Ready to show your sensitive side? The Alibi is a tiki-themed classic that has in its possession the best karaoke playlist in Portland. Belt out some Marvin Gaye while your date holds your Mai Tai, or snuggle up on their delightfully tacky red pleather booths.

Trying to squeeze every second out of the evening? Designed to please Portland’s elite cadre of waiters and bartenders, Shift Drinks is open until 2:30 AM every morning and utilizes every type of alcohol to its highest potential. If you are looking for someone who knows exactly what you and your date are craving at the end of the perfect evening, expect to find them here.

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