#1 Audio Tour Exchange. You agree to meet at a pleasant spot with an interesting landscape around it. You each record 10 minutes of audio near the spot, describing where you are walking, what you notice, what you are doing and thinking. Then you trade audio tours and experience each other’s noticings and thoughts.
#2 Briefcase. Before your date, you each pack a briefcase with various props inside and an assignment to do something with the props. At the beginning of the date you take trade briefcases and go off on your missions, then come back together and share how it went.
#3 Hiding Snacks. You split up. You each buy or prepare a snack, hiding it out in the city for your friend to find and eat. After you hide it, text them the location. When you find the snack, eat it slowly and take notes about the tastes and the location. Then, send the notes to each other.
#4 Why Not. You take turns making proposals for simple actions you can take together. After each proposal, you can make a list of reasons to do it, and reasons against. You have a simple rule: you will take all actions proposed unless there’s a strong reason against.
#5 Social Snowball. You’ll find a place with many people that you can observe at a distance. You’ll pick a person and together, guess what they’re like. Then you’ll approach them and check if your guesses were correct. Ask them if they want to join the game and continue. Variation: instead of guessing about people’s lives and characters, guess about their fantasies. More like this: If you like this, check out Stranger Danger, a more formal version.
#6 No Reply. You set a timer and until it is finished, you agree to never reply to each others’ statements — making every statement a non sequitur — and also to limit yourselves to one spoken sentence at a time. (Idea developed with Nathan Vanderpool)
#7 Out of Character. You each make a list of how you try not to be seen — as rude, racist, weak, and so on — and take turns practicing being the way you normally try not to be seen, and checking to see if there are any advantages of it you might have missed.
#8 No Compromise. Best for blind dates. You set a timer every 20 minutes or so. When it goes off, you either agree to immediately do something risky, or you end the date. You decide nonverbally. One way is if you both make a fist, and open them at the same time, and if both fists contain coins the date continues and you do something risky. Maybe trespassing, making out, calling an old friend — whatever seems risky for both of you. If either fist is empty, you separate without speaking.
#9 Shared-Soundtrack Walking. You take 10 minutes to make a playlist together that lasts at least an hour. You get it on both phones, put on earbuds, and press play simultaneously. You go out together, and you don’t talk or pause until it’s done.
#10 Discovery Golf. You are outside and there is no talking. You walk together. One of you will stop and face some kind of object or scene — a tree, a fence, a building. The other notices and stops too. You both contemplate the scene for a minute or two, then both give it a round of applause and continue walking. Optionally, one player may modify the scene and contemplate it again before continuing.
#11 Telephone Telepresence. You go to different, interesting locations and call each other. Don’t tell each other where you are. At first, you are the “robot” and your friend is the “operator.” Your friend asks you to move in a certain way, or to report back about your sensations or what you see. So your friend gets to explore your environment remotely, through your words. You get to investigate things you never would you were in charge of your own actions. Switch after 10 minutes. Variation: Blindfold the robot.
#12 Teach Me Something. You start as the “mentor”, and your friend is the person who is mentored. Your friend is allowed to point at anything in the environment and ask questions about it. They can also ask to learn certain skills, or to have certain kinds of experiences. You can both use this PDF, which provides menus of questions to ask about the environment, and types of skill and virtues and experiences to ask for.
#13 Aversion/Attraction Dice. You’ll play this while doing other things. Every 10 or 20 minutes, you’ll roll a six sided die. If the number is 1 or 2, you share something about the other person that attracts you; if it’s 3 or 4, something repulsive or that you’re averse to; if 5 or 6, something you could care less about.
#14 Co-Counseling. You’ll set a timer for 5 or 10 minutes, and you’ll listen while your friend says what they’re feeling in the moment, each moment. They can use words or they can use body movements or even dance. They can also rest. You just listen and watch, but your friend is telling a story or making an analysis, you can bring them back to what they’re feeling. You can also offer a hug if that seems appropriate. This is a thing.
#15 Dark Dance. The idea of this game is to hang out with each other while imagining something that scares you deeply, or something you hate, in the room with you. Start by just sitting near each other and separately imagining these dark things. Later if you like you can start to dance.
#16 Doubt Club. Sitting in a safe, quiet place, you’ll each share three doubts about your life. First, a doubt about something you did today, or something you are working on, or planning. Next, a doubt about your career or your long term plans. Finally, a doubt about your mission on Earth, or what’s meaningful or worthwhile
#17 Dream Teams. You say something you really want out of life or some impact you want to make on the world. Your friend has to come up with a “dream team”: a group of people — ideally with names and email addresses — who would be the best on the planet for making your idea work out. Switch roles. Variation: instead of a dream team, respond with one question which changes the person’s sense of how to pursue their dream.
#18 Director. You are the “actor” and your friend, the “director.” Your friend gets to describe a scene which includes you acting a certain way, and in a certain posture or character, in a certain setting. You do your best. Your friend can adjust the scene a few times, then you switch turns.
#19 Free Critical Discussion. With a sign that reads “Free Critical Discussion,” you’ll stand together somewhere with lots of foot traffic. People will queue up to talk with you. You’ll ask them if they have a topic they want to talk about and suggest a few sample discussion topics if they don’t. After a while, the people in the queue will notice they can talk with each other directly instead.
#20 Want to Play a Game? Try this if you’re bored of these adventure dates. You just asks, every once in a while, if your friend wants to play a game. If the answer is “yes”, then you make up a new game on the spot. Trade roles.
These activities were developed over many years and in collaboration with many people. Thanks especially to Rob Ochshorn, Bianca Cheng Costanzo, Maya Block, Tristan Harris, Aza Raskin, Mike Marotto, Anna-Lorraine Selke, Lisa Charlotte Rost, Brecken Rivara, Albert Kong, Sara Thacher, Bethany Colden, Alex Jarrett, Divya Manian, and Rythea Lee.