75 Questions to Ask on a Second Date

So you’ve gone on a first date and things went well enough that you’re both interested in going out again. Now you need to make sure that the second date is just as good, if not better than the first. One way to do that is by coming prepared with some questions to ask. Here are some of our favorites.

75 Questions you can ask on a second date:

  1. What are your favorite hobbies?
  2. What kind of music do you like?
  3. What are your favorite movies?
  4. What kind of movies do you like?
  5. What are your favorite TV shows?
  6. What are your favorite books?
  7. What are your favorite sports teams?
  8. What is your favorite food?
  9. What are your favorite places to eat?
  10. What are your favorite vacation spots?
  11. What is your favorite color?
  12. What is your favorite sport?
  13. What is your favorite season?
  14. What is your favorite animal?
  15. What is your favorite flower?
  16. What is your favorite thing to do on a weekend?
  17. What is your favorite holiday?
  18. What is the last book you read?
  19. Who are some of your favorite authors?
  20. What are you looking for in a relationship?
  21. Do you prefer to read, watch TV, or play video games in your free time?
  22. Do you have any siblings?
  23. Where did you grow up?
  24. Have you ever traveled outside of the country? If so, where did you go and what did you think of it?
  25. Do you have any close friends or family members that live far away from you?
  26. If so, how do you keep in touch with them?
  27. Do you have any plans for the future that you’re excited about?
  28. Do you have any fears or phobias that I should know about?
  29. What is your family like?
  30. Do you have any pets?
  31. Are you looking to get any pets in the future or do you think they’re more trouble than they’re worth 
  32. Where did you grow up?
  33. Where did you go to school?
  34. What is your job?
  35. Do you like your job?
  36. What are your goals for the future?
  37. Do you want to get married?
  38. Do you want to have children?
  39. Do you have any pet allergies?
  40. Do you have any medical conditions I should know about?
  41. What is the best thing that has ever happened to you?
  42. What is the worst thing that has ever happened to you?
  43. If you could have any job in the world, what would it be?
  44. If you could live anywhere in the world, where would it be?
  45. If you could have any superpower, what would it be?
  46. If you could meet any celebrity, who would it be?
  47. If you won the lottery, what would you do with the money?
  48. Are you a morning person or a night person?
  49. Do you prefer summer or winter?
  50. What is the best thing about your job?
  51. Worst thing about your job? 
  52. If you could retire tomorrow, would you, and why or why not
  53. What kind of car do you drive?
  54. What is your favorite type of car?
  55. What is your dream car?
  56. Where do you live?
  57. Do you own or rent your home/apartment/condo/house?
  58. How long have you lived there? 
  59. Do you li it there or are you looking to move? 
  60. If you could move anywhere, where would it be and why does that location in particular interest you so much? 
  61. What did you do today? 
  62. How was your week? 
  63. Tell me one fun fact about you. 
  64. What are you passionate about? 
  65. What were some of your favorite childhood memories?
  66. What are your hopes and dreams for the future?
  67. What has been the most meaningful and significant relationship in your life?
  68. What are some of the things that make you who you are?
  69. What makes you happy?
  70. What do you do when you’re feeling down?
  71. What are some of your biggest accomplishments?
  72. What have you always wanted to do but haven’t yet had the chance?
  73. What do you think is the key to a successful relationship?
  74. What has been your most difficult experience in life and how did you get through it?
  75. Who are the people that have had the biggest influence on your life and why?

Frequently Asked Questions

Should I kiss on the second date?

There’s no right answer to this question, as it depends on your own personal preferences and what you feel comfortable doing. If you’re not sure if you want to kiss your date on the second date, or if you’re waiting for a specific signal from them, then it might be best to just ask them directly. This will help avoid any potential awkwardness if one of you was expecting a kiss and the other wasn’t.

How do you know if a second date went well?

If they paid attention to you and seemed interested in hearing about your day, that’s a good sign. If they were polite and didn’t seem put off by your conversation, that’s also a good sign. If they asked about seeing you again and seemed happy when you said yes, that’s the best sign of all. If they do any or all of these things, your date probably went well.

How do you secure a second date?

First, try to find common ground with your date. If you find something you both enjoy, the second date will be much easier. You’ll already have something to talk about, and you’re more likely to have a good time.

Another tip is to be yourself. Don’t try to be someone you’re not; your date will see through that and it’ll only get awkward. Just relax and be yourself – you already have something in common with your date, so there’s no need to hide it.

Finally, don’t be afraid to make the first move. If you want to see your date again, let them know! A little confidence can go a long way when it comes to dating.


Asking questions on a date can be tricky because if they are too personal, your date might feel uncomfortable. However, if they are too mundane, the conversation between the two of you might feel awkward and forced, because small talk can only carry a conversation so long before it starts to feel repetitive and dull. Instead, try out some of these questions on your next second date.

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