Guide

Comfort zone challenges to do with a friend

It is easier to try something new when someone else is trying it too. Fifteen ideas for two people, from easy to bold.

Updated October 28, 2026

A challenge is easier to start, and harder to skip, when someone is in it with you. A friend gives you a reason to follow through and someone to share the story with afterwards.

Why it helps

Easy

  1. Walk around a neighborhood neither of you has explored.
  2. Have lunch somewhere neither of you has been.
  3. Make a playlist for each other's mood today.
  4. Each send a thank-you message to someone who helped you this year, then compare.
  5. Pick a street at random and walk it for 15 minutes.

Medium

  1. Try a sport or a fitness class neither of you has done.
  2. Cook a dish from a cuisine neither of you has made.
  3. Spend an afternoon as tourists in your own city.
  4. Go to a place you picked by asking a stranger for a recommendation.
  5. Each take 10 photos of the same object, then compare how differently you saw it.

Bold

  1. Take a first lesson together in something that makes you both a little nervous: climbing, kayaking, surfing.
  2. Go to an event neither of you knows anything about.
  3. Each make a reasonable request you expect to be turned down, and report back.
  4. Perform something for each other: a poem, a song, a joke.
  5. Plan a day trip where one of you chooses the place and the other shows up with no plan.

How to do it

Pick a challenge together, decide a day, and send each other a message when it is done. If you live in different places, do the same challenge on the same day and compare. See our 30-day plan if you want a ready-made list.

Boldly

Boldly has a duo mode

In Boldly you can send a friend one link to a specific challenge. Your friend sees whether you did it, and your name. A photo is shown only if you choose to share it. Duo challenges are free.

Download on theApp StoreFree to download. iPhone.

Questions about challenges with a friend

Does my friend need the app?

For duo challenges in Boldly, your friend opens the link you send. You can also do any challenge from this list without an app.

What does my friend see in Boldly?

Only whether you did the challenge and your name. A photo is shown only if you choose to share it.

What if my friend does not want to?

Do it alone. You can also try our challenge generator and send them the result later.

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