Adventurous Questions for Friends (That Are Literally About Adventuring)

Pegg Deep
4 min readMar 21, 2018


You don’t have to be in the woods to tap into your adventurous side.

If you read these questions for friends out loud and try to guess who would answer what, you deepen the human connection. Feverishly friendly debates are a certainty.

A long-lost relative I never met died and left me a fixer-upper cabin deep in the woods.

  1. I’d go up there and leave it as is. Spooky, spooky.
  2. I’d hire a real estate agent, sell it, and never go up there. Too creepy.
  3. I’d fix it up and use it as a vacation home.
  4. I’d fix it up and rent it out as an Airbnb or sell it.

These questions for friends may make you stop and dream for a bit, like the first one… and pretty much all of them.

Which space excursion would I be most down for?

  1. Going up to the moon and bouncing around.
  2. Being one of the first on Mars. (Year-long roundtrip travel time.)
  3. No training, just going up into orbit.
  4. Being able to remote control a probe to explore our solar system from earth.

You might not think controlling a drone to explore the cosmos is all that adventurous, but that would be my choice. No risk, all reward.

This adventure would be the most appealing.

  1. Kayaking surrounded by humpback whales and dolphins.
  2. SCUBA diving the Great Barrier Reef.
  3. Racecar driving around an open track in Monte Carlo.
  4. Mountain climbing Mount Kilimanjaro.

Asking adventurous questions for friends and with friends is a great time to just get up and go.

Which daring social act would be the easiest for me?

  1. Asking a stranger to coffee.
  2. Ask if I can join someone who sits alone at a restaurant.
  3. Asking someone to dance at a party.
  4. Gathering 100 signatures for a petition.

You don’t need to be clearly away jungle hangings with a machete in order to have an adventure.

A close friend shows up and says, “Come with me now, and you can’t ask any questions.”

  1. I’d have 9–1–1 typed and ready. My friends are crazy.
  2. I would immediately start with the questions.
  3. Call in sick to work tomorrow. It’s going to be a long night.
  4. I’d simply ask: “Who’s driving?”

A good friend is always honest with you. If you’re not around “good” friends, they will be by the end of these questions for friends. Guaranteed, or your money back.

I’m called upon to save the world and can only bring along one companion.

  1. A parent. They always know what to do.
  2. My significant other. We make a great team.
  3. A close friend. Lock and load, partner.
  4. A sibling. “Here we go again.”

Gordon Ramsay is absolutely brutal. He could definitely use some Pegg action.

I’m sent on an adventure, but I don’t know what it will entail. I’d bring…

  1. Snacks. Can’t conquer on an empty stomach.
  2. Booze/some weed. What can’t I do just a bit buzzed?
  3. A weapon. On guard. Touché.
  4. Various clothing in prep for different climates.

All right, now everyone can start packing!

And on your way to your next big adventure, you might as well keep the questions, answers, and gifs coming by downloading the Pegg mobile app.

Originally published at Gratzi.



Pegg Deep

Helping humans get to know each other, one chuckle at a time.