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Random questions to ask when you want something new

40 numbered random questions. Pick a number from 1 to 40, roll for it, or let someone else choose, and answer whatever comes up.

Keepsake · Family storytelling publisher Published Dec 21, 2025 Updated Oct 3, 2026

In this topic: Skills

Quick starters

Use these questions to spark an easy conversation.

  • What is your most controversial pizza topping opinion?
  • What is the oddest thing you have found in a coat pocket?
  • Which song should play every time you walk into a room?
  • If your pet could talk, what would it complain about first?
  • What question should I have asked you instead of this one?

All questions

40 questions. Choose the ones that suit your conversation.

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Conversation guide

These 40 random questions are numbered so chance can choose for you. Ask someone to pick a number from 1 to 40, or use a random number generator on your phone, and answer whatever comes up. The mix runs from pizza opinions to childhood smells, so no two rounds feel the same.

Ways to play

  • Call a number. Go around the room. Each person names a number for the next person to answer.
  • Roll dice. Roll two dice for a number from 2 to 12. Add 10, 20 or 30 to reach the later questions, and roll again if you land above 40.
  • Draw from a jar. Write the numbers on scraps of paper and keep the jar on the table or in the car.

If a question falls flat, roll again. If one gets a big reaction, stay with it for a while before moving on. The last question, number 40, is a good one to end on.

Other lists for the same mood

For quick picks between two options, try this or that questions. For stranger, more absurd questions, see weird questions. For a long drive, use our road trip questions.

Helpful follow-ups

  • Why that one?
  • Has that always been true?
  • Who would answer that the opposite way?

Frequently asked questions

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