wikiHow Questions to ask a Stranger Over Text 1. What do you like to do in your free time? 2. What's your favorite type of music or artist? 3. What's your favorite book or movie? 4. What's your favorite type of food? 5. Do you have any hobbies or interests? 6. What's your favorite place you've ever traveled to? 7. What's your favorite way to relax? 8. What's your favorite thing about your job? 9. Have you learned any new skills recently? 10. What's your favorite sports team or athlete? 11. What's your favorite holiday and why? 12. What's the best concert or show you've ever attended? 13. What's your favorite type of cuisine to cook or eat? 14. What's your favorite animal and why? 15. What's the most interesting place you've ever been to? 16. What's the most exciting thing that's happened to you recently? 17. What's a goal or dream you're currently working towards? 18. What's the most adventurous thing you've ever done? 19. What's the best advice you've ever received? 20. What's something you're looking forward to in the near future? Page