Support Us Button Widget

Play ‘Would You Rather’ with us, Portland

We whipped up some pretty tough questions. Feel free to use them at your next get-together.

A soft pink sunset casts on Mount Hood, which rises above the Columbia River and floating homes.

Would you rather only ever see sunrises or sunsets?

Photo by @imsuvigya

Table of Contents

When was the last time you played a game of “Would You Rather”?

In case you’ve never played, here’s a quick rundown:

Step 1 — A question is posed that pitches two options. Example: “Would you rather live in Portland, Oregon, or any other city in the world?”

Step 2 — You decide what you’d rather do. No surprise here; we’re saying the Rose City.

Now that you’re a “Would You Rather” expert, let’s tap into our inner middle schoolers and play this nostalgic game featuring some of Stumptown’s most iconic landmarks, qualities, and foods.

Don’t worry, we won’t ask you anything gruesome or anxiety provoking (that’s not really our style).

Submit your answers.

Question one

Would you rather live inside of Powell’s City of Books or the Portland Art Museum?

  • Give me unlimited bedtime reading material.
  • Paintings put me at ease.

Question two

Would you rather never use an umbrella when it’s raining OR only wear long-sleeved shirts and pants in the summer?

  • A rain jacket is all I need.
  • At least I’d save money on sunscreen.

Question three

Would you rather be an extra in an episode of “Portlandia” OR appear in a Portugal. The Man music video?

  • Step aside Fred and Carrie, I’m taking this skit (even more) off the rails.
  • The thrill of hanging with the band? I “Feel It Still.”

Question four

Would you rather eat for free at Fire on the Mountain for the rest of your life OR never pay for beer again at the brewery of your choice?

  • Unlimited wings? Yes, please.
  • Take one down, pass it around...

Question five

Would you rather score a game-winning goal against Seattle in front of a packed Providence Park OR drain a buzzer beater to send the Trail Blazers to the NBA Finals?

  • Build a bonfire — I’m putting one in the net.
  • Rip City, we’re gonna party like it’s 1977.

Question six

Would you rather only be able to use the St. Johns Bridge OR the Sellwood Bridge to cross the Willamette River?

  • NoPo’s views are hard to beat.
  • Southeast Portland is my stomping grounds.

Question seven

Would you rather give Jolene the baby orangutan a hug OR get five minutes to pet Moshu the red panda?

  • Have you seen the little cutie’s flaming locks of auburn hair?
  • If you can find Moshu, I’ll give him the scritches.

Question eight

Would you rather experience Portland 100 years ago OR 100 years in the future?

  • Take me back.
  • Show me the future.

Thanks for playing, Portland. Is there a “Would You Rather” question about the City of Roses that you’d like to see answered? Send it our way and we might just pose it to your fellow readers.

More from PDXtoday
The annual festivities give sneaker enthusiasts the chance to brush shoulders with creatives and leaders in the footwear industry.
This week — Monday, July 22-Friday, July 26, 2024 — we’re shining a spotlight on the vibrant drink scene in Portland.
The property on the way to Mount Hood offers animal tours, hosts private events, and has Airbnbs to reserve for your next getaway.
The touring show “Kooza” will run from Wednesday, Aug. 21 to Sunday, Oct. 6 at the Portland Expo Center.