I have a confession, I’m consistently enamored with Portland! I love the downtown with its turn of the century architecture, and over abundance of restaurants. I’m beyond beguiled at the bounty of boutique hotels, with their warm inviting foyers, trendy accents, and unique perks. I’m delighted that downtown is walkable, so you can stuff your face at one place, then round the corner to the food carts and stuff yourself there too! I enjoy jogging along the banks of the Willamette river in the summer, so I can sweat out the calories, in order to binge eat some more!
This is a gem of a city in the Pacific Northwest that actively embraces the motto “Keep Portland weird”. It surprises me how many creative culinary endeavors a small city can support. Do you want authentic Isaan Thai Food from the interior of Thailand? You got it! How about satiating that midnight doughnut craving? Got that too! Do you want to grab a drink in an old 50’s style bomb bunker turned specialty cocktail lounge? Of course they got it!
Do you see a pattern in my love for Portland? It has a seemingly endless amount of restaurants to entertain and satiate even the pickiest eater. There’s a plethora of dining options, which happily overcompensates for this unassuming city in the Pacific Northwest. But with so many options, therein lies the dilemma. What to do, and where to eat on date night? The possibilities are mind boggling, almost resulting in analysis paralysis for the sheer number of combinations. I enjoyed preparing for our date night by reading blog posts and reviews. This post by Wandering Soles was especially entertaining:
Things To Do in Portland – Wandering Soles
We ended up picking out an easy to walk journey through some of the trendiest entertainment spots in downtown. For a short weekend in Portland, it was really hard to pick as I really wanted to eat and drink all of it! Our jaunt is heavy on eating and drinking, and is only one example of how to spend a 5 hour date in Portland Oregon.
So how does one fit it all into one night? Very carefully, with a little bit of walking and stretching your stomach. Here’s how it went:
We started with a cool underground location for drinks. Literally….this place is underground. Pepe Le Moko is a subterranean bar serving up classic cocktails and snacks. As the menu will tell you, its named after a French film about a criminal hiding in Algiers. I get it, ok. Its an underground, dark hiding location, like the criminal in the movie. And yes, the drinks are as cool and trendy as the location! With limited seating, we were lucky to be there early enough not to have to wait for booth seating. Admiring the other patrons, the waitress mentioned it was a popular pre drink location for dates heading to the Living Room Theater for a movie.
Liquored up but not quite ready for dinner, we start playing games with each other. Literally! (Again) We walked to Ground Kontrol for some old school arcade and pinball action. I really feel sorry for the under 21’s who can’t join us here, because this place was a blast! Three large rooms and a loft of nostalgic arcade games and pinball machines ranging in price from 25 cents to $1.00 each. A stack of quarters could keep you busy for a while. Oh, and there’s alcoholic beverages and hot dogs as well, perfect for appetizers before dinner!
But why would you want to fill up on hotdogs when you have Andina to look forward to. It would be like filling up on miller light when you have Dom later. Andina is an impressionable dinner location with reliably tasty tapas, in the form of Peruvian shareable plates. The service staff were friendly and ready for recommendations for our questions. We were feeling formal, so we bypassed the casual bar area with guitar player, and opted for a seat in the dining room. We ordered about 4 shareable plates, and this was more than enough food for 2 people. Their ceviche was amazing!
Now sufficiently stuffed, what is there to do? Search out an aperitif! Having a drink at Multnomah Whiskey Library feels like you stepped into your rich step uncle’s Rockafeller boardroom. This place is swank, with about a billion liquors to choose from. Okay maybe only a thousand or so, but its pretty intimidating. Luckily the bartenders are super professional, asking what flavours we enjoyed and whipping up creative drinks accordingly. It was a busy night, so we did have to wait to ascend into the main room, but the bottom bar called the Green Room serves up enough cocktails to keep you busy.
I really feel for the single people planning a date night in Portland. With so many creative foodie options, it’s probably really hard to impress a date! After all was said and done, we had paid a pretty penny to keep the night going. But in our opinion, it was worth it for the stories, and a good dive into the Portland Dining and Drink scene. Here’s the Google Maps route if you feel inclined to try it yourself:
If the date heads into morning, head over to Cheryl’s for their Portuguese fried rice. (Wink wink!)
What are some of your favorite places for date night in Portland?
Feel free to pin this story!