40 This or That Questions for Friends

These 40 this or that questions for friends give you two choices and somewhere to take the conversation afterward. Pick five, take turns answering, and ask about one choice that surprises you. You can play face to face or send a question in your usual chat. No account, score, or finished list is required.

Start with easy and funny choices, try time and plans, compare friendship preferences, or choose something a little more thoughtful. The later groups work best when you are both comfortable explaining your answers.

Easy and funny this or that questions

1. A kitchen that narrates your cooking or a wardrobe that reviews your outfit?
2. A tiny trophy for every finished chore or applause whenever you catch the bus?
3. Choose a film by its poster or a book by its opening sentence?
4. A picnic with excellent sandwiches or a cafe with excellent chairs?
5. Your pet chooses your music or your youngest relative chooses your haircut?
6. A souvenir you can eat or one you can wear?
7. A perfectly organized snack drawer or a mysteriously endless one?
8. Be the friend with a spare charger or the friend with emergency snacks?
9. Win a very serious board game or invent a very silly one?
10. Find a secret garden on your usual walk or a secret bakery on your commute?

Try a follow-up: After the picnic or cafe choice, ask "What would make you stay for another hour?" Your answers might give you an idea for your next afternoon together.

Questions about time and plans

11. Book one highlight for a trip or leave every day open?
12. Meet briefly every week or spend a whole afternoon together once a month?
13. Arrive early and explore nearby or arrive exactly when the plan starts?
14. Make dinner together or each bring something already cooked?
15. Revisit a favorite place or try somewhere neither of you knows?
16. Have a regular walking route or take a different turn every time?
17. Spend a free morning learning something or finishing something?
18. Pick the destination or organize how you get there?
19. Keep a backup plan or enjoy an unexpected change?
20. Leave an outing while you still have energy or stay for one last thing?

Try a follow-up: After the weekly or monthly choice, ask "Would that change during a busy month?" A preference is not a promise. You are finding out what sounds good, not negotiating how often someone must see you.

This or that questions about friendship preferences

21. A friend remembers your usual order or a story you told months ago?
22. Receive a funny photo during a busy day or a thoughtful message afterward?
23. Catch up while walking or while making something?
24. Be invited to join a friend's hobby or introduce them to yours?
25. Celebrate good news with a small tradition or something different each time?
26. Receive a specific offer of help or be asked what would help?
27. Talk through a disagreement straight away or agree on a time after cooling down?
28. Keep a shared list of plans or suggest things as they come up?
29. Hear a voice note with a story or get the story in written messages?
30. Spend quiet time alongside a friend or meet when you both feel like talking?

Try a follow-up: After the help question, ask "What would a useful offer look like for you?" You can give your own example first. Neither choice makes someone a better friend.

Thoughtful choices without demanding a personal confession

31. Become more patient with learning or more willing to begin?
32. Have a free hour with no interruptions or an afternoon with no decisions?
33. Be remembered for making people laugh or making them feel included?
34. Get better at asking for help or saying when you need space?
35. Preserve an old tradition or start a new one with friends?
36. Learn how a friend sees your hometown or show them a place that matters to you?
37. Have more small things to look forward to or one big plan on the horizon?
38. Finish a creative project privately or share it while it is still taking shape?
39. Receive encouragement to keep going or permission to change direction?
40. Keep a record of ordinary good days or memorable first experiences?

Try a follow-up: After the small things or big plan choice, ask "What would you put on the calendar?" Stay with the example they choose to share. You do not need to ask why their life is not already that way.

How to play with two friends

Choose five questions from one group. One person reads or sends a question, both answer, then swap who goes first. A short reason is welcome; a personal explanation is optional. Allow "both," "neither," or "it depends" if the two options do not fit. Either person can skip or stop.

Here is an invented example of turning a choice into an exchange:

You: Revisit a favorite place or try somewhere new?

Them: Favorite place. I like knowing what I am looking forward to.

You: I usually pick somewhere new, but I get that. Is there a place you would happily go back to this weekend?

If the answer starts a story, leave the list and listen. There is no bonus for completing all 40. Over text, send one question and let the other person answer before adding another. A game invitation does not require an immediate reply.

What if your choices are different?

Ask what they pictured. "A whole afternoon" might mean a long walk to you and sitting quietly together to them. Different answers can come from different situations, budgets, or energy levels. Avoid counting matches as a friendship score or treating one answer as a permanent description of someone.

If you want open-ended prompts instead of two choices, try our deep questions to ask friends. If the real issue is running out of things to say between prompts, our guide to keeping a conversation going over text shows how to follow a detail and share your own side.

Want one question with a private answer reveal?

ValuePair offers a separate daily question for two. Pick an answer, create a private link for one person, and send it directly to your friend if they want to try it. Your choices appear after both people answer. Neither person needs an account or has to join matching.

The daily question is multiple-choice and may offer more than two options. It is not this list, and you cannot choose or enter these 40 prompts in the activity. For these questions, stay in your own chat. For the daily activity, return to that chat after the reveal to talk about what made you choose your answer.

Editorial note

ValuePair wrote these prompts and publishes this guide. They are conversation suggestions, not a tested measure of friendship or a promise of closeness. The example exchange is invented. The optional daily activity is a ValuePair product; the public FAQ describes the separate matching experience.