image of couple thinking of conversation starters for date

One of the most difficult things about dating in the flesh is figuring out what to talk about with your date. If you’re stuck on conversation points for your next date, you’re not alone. We’ve compiled the following list of 75 conversation starters for dating to help you get the chit-chat rolling and get to know your date better. The next time you get stuck, give one of the following questions a try and see where the conversation takes you!


75 Conversation Starters for Dating


  1. What’s something people would be surprised to learn about you?
  2. Is your adult life what you pictured it would be when you were growing up? 
  3. If you could remain any age forever, what age would you choose? Why?
  4. What is something that other people love, but you don’t?
  5. Do you have any unpopular opinions? What are they?
  6. What is your favorite childhood memory?
  7. What is the most bored you’ve ever been? What helped with the boredom?
  8. What is your best friend like? How long have you been friends?
  9. Do you prefer to go out in groups or one on one?
  10. Do you prefer noisy and busy or quiet and calm?
  11. Have you ever wanted to walk out on a date? How did you handle it?
  12. Routine or spontaneity? 
  13. In school, were you a goofball, a theater kid, an academic, or sporty?
  14. What is the weirdest thing that’s ever happened to you?
  15. If you could spend an hour with anyone (alive, deceased, fictional, or real), who would it be? What would you do?
  16. What gets you through the hardest days?
  17. What are you most proud of?
  18. Do you have any personal projects you’re working on?
  19. What is your ideal balance between work and life?
  20. If money was no issue, would you live your life differently?
  21. What’s on your bucket list?
  22. Do you have any regrets in life?
  23. If given the chance, is there anyone you would apologize to?
  24. What is an ideal day like for you? 
  25. Dogs, cats, or snakes? Why?
  26. In your mind, what makes for a healthy relationship?
  27. What has been your biggest lesson in life? Who was your teacher?
  28. What is your favorite way to celebrate?
  29. Spend or save, and why?
  30. Would you rather volunteer with children or the elderly? Why?
  31. What is your idea of romance?
  32. What is one date idea you’ve been dying to try but haven’t had a chance to do yet?
  33. Stay local or travel? Why?
  34. What are your top three dealbreakers in a relationship?
  35. Do you believe in soulmates?
  36. Where do you think we go after this life? What do you hope happens?
  37. Do you believe in luck? Or does luck favor the well-prepared?
  38. Do you have a favorite family member? Why?
  39. Who is your favorite role model from childhood?
  40. What is something you think people might assume about me?
  41. What is something people assume about you?
  42. Elevator or stairs? Why?
  43. Fondest birthday memory?
  44. What is one thing you’d change about this building/place?
  45. Are you a thinker or feeler?
  46. What is one thing you’d never change about yourself?
  47. Massages: Relaxing or uncomfortable?
  48. Do you like public displays of affection or do they make you uncomfortable?
  49. Do you like to lead, be part of the group, or do your own thing?
  50. When did you realize Santa wasn’t real?
  51. What is your favorite holiday? 
  52. Text or call?
  53. 5 minutes early or 5 minutes late?
  54. Inside or outside?
  55. What are you passionate about right now?
  56. Do you have any habits you’d like to change?
  57. Hiking or swimming?
  58. What do you love most/least about your career?
  59. What do you wish was different about our culture/society?
  60. Are there any organizations you support? 
  61. Favorite way to relax?
  62. Are you feeling nervous about our date?
  63. If you’re interested in someone, how would you show it?
  64. Speak your mind or keep the peace? Why?
  65. Do you have any pet peeves?
  66. Hot date on the town or quiet, romantic night in?
  67. How are you most different from your parents? How are you the same?
  68. Do you have a big or small family? 
  69. Do you have a favorite sibling or cousin? What makes them your favorite?
  70. Funniest dating story?
  71. What is one thing you think everyone should try at least once?
  72. Do you consider yourself adventurous or do you prefer to stick to what you know?
  73. What is something you want to know about me but are shy about asking?
  74. Do you typically know when someone is flirting with you?
  75. How do you hope this date will end?


So, which of the 75 conversations starters for dating was your favorite? Do you have a few you’ll hang onto for when you’re stuck wondering what to talk about with your date? Did our list inspire some of your own conversation starters for dating? 


Here’s wishing you deep connection, stimulating conversation, and successful dating! As always, if you need a little support as you venture through the dating world, our relationship coaching can help. Don’t be afraid to reach out – you don’t have to navigate this alone!