wikiHow Fun Questions to ask Over Text Here are 20 fun questions to ask over text: 1. What's the most adventurous food you've ever tried? 2. If you could travel anywhere in the world right now, where would you go? 3. What's the best prank you've ever pulled? 4. If you could only listen to one song for the rest of your life, what would it be? 5. What's the most ridiculous thing you've ever bought? 6. What's the craziest dream you've ever had? 7. If you could have any superpower, what would it be? 8. What's the funniest meme or internet joke you've seen recently? 9. If you could have dinner with any historical figure, who would it be? 10. What's the most spontaneous thing you've ever done? 11. What's your favorite cheesy pickup line? 12. If you could trade places with any fictional character, who would it be? 13. What's the most embarrassing moment of your life? 14. If you could only watch one movie or TV show for the rest of your life, what would it be? 15. What's the weirdest thing you've ever eaten? 16. If you could have any animal as a pet, what would it be? 17. What's the most interesting book or article you've read recently? 18. If you could witness any event past, present, or future, what would it be? 19. What's the most unusual talent you have? 20. If you could live in any fantasy world, which one would you choose? Page