Conversation Starters Part 2: 50 Questions You Haven’t Already Asked Your Date

If you think you know everything about the person you’re dating, these questions will prove otherwise. Going on a first date? Find conversation fodder on this list.

Fair warning: Consider your audience. You’re no doubt too cool to ask a virtual stranger to name a favorite school supply (Question #8), but anyone can talk about a habit that was hard to break (Question #6) if the subject’s introduced naturally into the conversation. If you’re loathe to spring any of these questions on a date, e-mail them to the contacts in your address book for the latest round of Getting to Know Your Friends.

  1. What’s your favorite Dr. Seuss book?
  2. If you could live in any home on a television series, what would it be?
  3. What’s the longest you’ve gone without sleep?
  4. What’s your favorite Barry Manilow song?
  5. Who’s your favorite Muppet?
  6. What’s the habit you’re proudest of breaking?
  7. What’s your favorite Web site?
  8. What’s your favorite school supply?
  9. Who’s your favorite TV attorney?
  10. What was your most recent trip of more than 50 miles?
  11. What’s the best bargain you’ve ever found at a garage sale or thrift store?
  12. Where were you on September 11, 2001?
  13. What’s your favorite tree?
  14. What’s the most interesting biography you’ve read?
  15. What do you order when you eat Chinese food?
  16. What’s the best costume you’ve ever worn?
  17. What’s your least favorite word?
  18. If you had to be named after one of the 50 states, which would it be?
  19. Who’s your favorite Care Bear?
  20. Describe something that’s happened to you for which you have no explanation.
  21. If you could travel anywhere in Africa, where would it be?
  22. What did you have for lunch yesterday?
  23. Where do you go for advice?
  24. Which do you use more often, the dictionary or the thesaurus?
  25. Have you ever been snorkeling? Scuba diving?
  26. Have you ever been stung by a bee?
  27. What’s the sickest you’ve ever been?
  28. What’s your favorite form of exercise?
  29. What’s your favorite Cyndi Lauper song?
  30. What did you do for your 13th birthday?
  31. Are you afaid of heights?
  32. Have you ever taken dance lessons?
  33. What’s your favorite newspaper?
  34. What’s your favorite Broadway musical?
  35. What’s the most memorable class you’ve ever taken?
  36. What’s your favorite knock-knock joke?
  37. What’s your favorite commercial?
  38. If you could go to Disney World with any celebrity alive today, who would it be?
  39. Do you prefer baths or showers?
  40. Does your chewing gum lose its flavor on the bedpost overnight?
  41. What’s your favorite breakfast food?
  42. Who’s your favarite game show host?
  43. If you could have a super power, what would it be?
  44. Do you like guacamole?
  45. Have you ever been in a food fight?
  46. Name five songs to which you know all the lyrics. (Better yet, sing them.)
  47. What’s your favorite infomercial?
  48. What’s the longest you’ve ever waited in line?
  49. What’s on the cover of your address book or day planner?
  50. Have you ever taken a picture in one of those little booths?

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