Side Quests With Friends: Pick a Dare, Crown a Winner - Social & Community quest for Beginner level adventurers

Side Quests With Friends: Pick a Dare, Crown a Winner

Give your friends a job, a dare and a tiny bet.

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Your mission

Three Photos, One Champion

Run one dare with your group in two to four hours and come home with three instant photos: the kickoff, the peak moment and the crowning. Winner takes the pot and chooses next week's dare.

Bonus challenge: Let someone pitch a wildcard swap before the midpoint. If the group cheers, you have to do it.

Saves it to your list, no account needed.
Time
2-4 hours per challenge
Cost
Supplies only
Starter gear from $18
The walk itself is free. Instant film runs about $0.70 to $1.00 per shot, so three photos cost a few dollars. Stakes are whatever you agree on, usually $5 to $10 each, and that money goes to the winner.
2 supplies · see the gear
Who it's for
friends, a group · Teens 14+ with an adult along; after-dark versions are for adults only
Level
Beginner
Where
Both
Season
Year-round

About This Quest

Round up three to six friends, pick one silly dare, and run it through your neighborhood this weekend. Someone leads the way, someone keeps score, someone guards the camera. Three instant photos mark the day: the hopeful start, the loud middle, and the moment a winner is crowned.

Your friends are brilliant at making plans and hopeless at finishing them. So give the afternoon a name, a scorekeeper and a few dollars on the line, and watch everyone suddenly care enormously about who wins. You'll pick one dare that matches the group's energy, hand out three jobs, agree on stakes of five or ten dollars each, then walk it out over two to four hours with a regroup in the middle. No planning genius needed: one clear dare is plenty. Stuck for a starter? Try these side quests to do with friends. Come home with three photos and one story nobody can tell the same way twice.

Why This Quest Matters

Hanging out often means sitting in the same room, scrolling in parallel. Give those same friends one goal, a job each and a few dollars on the line, and people start shouting, arguing about rules and looking out for each other at the crossings. The photos end up on a shelf. The inside jokes last much longer than that.

What You'll Experience

  • Hand out the jobs: One friend leads the route, one keeps score, one guards the camera.
  • Play for real stakes: Five or ten dollars each makes everyone suspiciously competitive.
  • Catch the peak moment: One instant photo, taken right as it all goes sideways.
  • Crown a champion: The winner takes the pot and picks what you do next time.

What You'll Need

Top gear to make this quest great.

Pull it off

Instant film pack

Three photos per outing at roughly $0.70 to $1.00 a shot, so one pack covers several sessions.

4.8 (113,214)
Get on Amazon · $18.17 — Instant film pack
Portable Bluetooth Speaker

Plays music on the walking stretches and runs your guess-the-song round for about five hours.

$39.95 — buy Portable Bluetooth Speaker on Amazon

As an Amazon Associate I earn from qualifying purchases. Prices may change.

Before You Begin

Round up three to six friends, because fewer feels thin and more turns into a parade. Pick your dare before anyone leaves the house. Bring an instant camera with a fresh pack of film, paper and a pen for the scores, small cash for the stakes, and a phone with a map. Check that at least two phones are above half battery before you set off. Handy extras: a small Bluetooth speaker for the walking stretches, and a pocketed photo album so the prints get a home. If a dare takes you onto private property or into a shop, ask permission first, and choose somewhere else if the answer is no.

Safety Tips

A good quest stays a good story. These are general notes; your gear's manual, the venue's rules and local law come first.

  • Tell one person who is not coming where you are going and when you expect to be back.
  • Private property and businesses need permission before you walk in. If a spot is fenced, posted or restricted, pick a different checkpoint instead of arguing with the sign.
  • Nobody crosses a street while looking at a phone or a camera. Phones down, heads up, cross together.
  • After dark, stay on well-lit streets the group already knows, keep everyone together, and never split up to cover ground faster.
  • If you bring the speaker, keep it out of the water despite its waterproof rating, and dry the charging port fully before you plug it in.

Step-by-Step Guide

1

Pick Today's Dare

15 min

Be honest about the group's energy, then choose one dare. Tired? Try the Stranger's Recommendation: ask five people for their favorite spot nearby and visit the best one. Buzzing? Try Color Hunt, racing in pairs to photograph something red, then blue, then gold. Or Mystery Corner: let a map app pick a nearby public spot and walk there. Agree what counts as finished.

💡 Pro Tips:

  • • If two people are torn between dares, do the easier one. Everyone has more fun when it actually gets finished.
2

Hand Out The Jobs

10 min

Three jobs, three people. The navigator decides where you head next. The documenter guards the camera and the three precious shots. The scorekeeper writes names on the paper and settles arguments. Then set the stakes: five or ten dollars each into one pocket, winner takes it all. Choose a midpoint spot to regroup, and agree nobody can swap the dare after that.

💡 Pro Tips:

  • • Give the quietest friend the scorekeeper job. They are almost always the fairest judge in the group.
3

Kickoff Photo

10 min

Before a single point gets scored, squeeze everyone into one frame and take your first instant shot. All of you in it, so prop the camera on a wall or ask a friendly passerby. Wave the print while it develops and pass it around. This is the before picture, and in two hours it will look wonderfully optimistic.

💡 Pro Tips:

  • • Write the date and the dare's name on the white strip under the photo while the pen is still in your hand.
4

Run The Dare

20 min

Off you go. The navigator leads, the scorekeeper calls out points, and everyone talks far too much nonsense. Put music on for the walking stretches and play a guess-the-song round between checkpoints. The second the thing tips into chaos, or someone pulls off something ridiculous, take the second photo right then, not afterwards.

💡 Pro Tips:

  • • Ask before walking into a shop or onto someone's property, and take a no cheerfully. There is always another checkpoint.
5

Midpoint Regroup

15 min

Meet at the spot you chose and let everyone report out loud. Scores get read, excuses get made, and anyone who wants a wildcard swap must pitch it with real enthusiasm right now, before the deadline passes. Check phone batteries, share the snacks, and decide whether the second half needs a rule to even things up.

💡 Pro Tips:

  • • Trailing badly? Offer double points on the last stretch. A comeback makes much better photos than a blowout.
6

Crown The Champion

20 min

Finish somewhere with seats. The scorekeeper reads the totals, the winner takes the pot, and last place earns a gloriously silly title like Keeper of the Wrong Turns. Take the third instant photo while everyone is still talking over each other. Back home, slot the kickoff and crowning shots side by side in the album so the before and after sit together.

💡 Pro Tips:

  • • The champion picks the next dare. After five to seven outings, sit down together and rank them worst to best.

You turned a vague group chat plan into an afternoon with a champion, a loser and three photos worth keeping. Hand the next dare to the winner and set a date.

Get another side quest
Full gear guide
Tabletop RPG Starter Kit: 10 Picks That Earn Their Table Space
See all picks →

Gear Up for Your Quest

You bring the curiosity. We've found the tools.

Pull it off

Instant film pack

Instant film pack

Three photos per outing at roughly $0.70 to $1.00 a shot, so one pack covers several sessions.

4.8 (113,214)
Get on Amazon · $18.17 — Instant film packdetails & deals →
+ complete the kit — 1 more
Portable Bluetooth Speaker
4.8 (53,438)

Plays music on the walking stretches and runs your guess-the-song round for about five hours.

Waterproof wireless speaker with 8+ hour battery

Get on Amazon · $39.95 — Portable Bluetooth Speakerwhat to look for & our pick →

RELATED GEAR GUIDE

Tabletop RPG Starter Kit: 10 Picks That Earn Their Table Space

Practical picks, real prices · Social & Community

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