100 Date Night Questions

What to talk about on date night: 100 questions + printable conversation cards

Good conversation is a date night essential, whether we're going "out on the town" or staying in for an at-home date. For me anyway. I loved the beginning, when we were simply friends learning each other's favorite color or favorite type of music. There's nothing like that quality time and intent in discovering the intricacies of the other person.

It's all too easy to lose that novelty. But there is still so much we can learn about each other; so many ways we can still grow our intimacy through conversation. All it takes is a couple questions to get that going. No interrogating (no need to ask all 100 questions at once); no vague "so, what's new with you?" Just a few questions spread throughout the date night, or even throughout the week.

Truth is, I usually stall out. I notice the lull in conversation, and I start with a prolonged "Whhhhaat..." in hopes that something fun, funny or profound will follow. Instead, all that slips out is a line from Monty Python and the Holy Grail: "What... is your favorite color?"

The other night that lead to a full conversation of our favorite Monty Python bits ("are you suggesting that coconuts migrate?"); usually, however, it helps to actually write a couple questions down. Just 3-4 to put in my purse or in my pocket and refer to when we start looking like that elderly couple in the restaurant that remains in silence throughout the meal.

Here are 100 questions. Really, once you get started with one or two, it's easy to progress the conversation naturally. I broke these down into 10 basic themes to help you start thinking about your own questions to bring up on date night. Enjoy :)

What to Talk About on Date Night

Current Favorites

Talking about favorites is an easy, fun, and neutral way to start any conversation. Favorites can also change regularly, so they're easy to cycle through (especially things like current favorite song).
1. color
2. song
3. restaurant
4. book
5. hobby
6. exercise
7. movie / tv show
8. app
9. video clip
10. indulgence

This or That

Beyond favorites, there's something about knowing if a person prefers a mac or a pc (for example) that can be so telling about personality and how they tick. These are similar to favorites and can be expounded on, but are great for rapid-fire, too.
11. sunrise or sunset
12. beach or mountains
13. camping or cruise
14. mac or pc
15. hot or cold
16. read or write
17. watch or play
18. outdoors or indoors
19. glasses or contacts
20. filthy rich or dirt poor

Would You Rather...

I have a friend that's great at asking "would you rather" questions. I'm not so much. But it can be fun to put creativity into coming up with different scenarios to choose from. What follows are some ideas, but certainly not as creative as this could go!
21. ... have the power of invisibility or telepathy?
22. ... live where the sun always shined or where it never did?
23. ... eat a cooked frog or live bugs?
24. ... have a great personality and be unattractive or have a terrible personality and be very attractive?
25. ... have no electricity or no water?
26. ... never have to clean the kitchen again, or never have to clean the bathroom again?
27. ... be deaf or blind?
28. ... trip and fall in front of 10 people you don't know, or say something embarrassing in front of 1 celebrity?
29. ... capture memories only in videos or only in photos?
30. ... not be able to read or not be able to count?

What would you do if...?

Start with a question and let them expound with the answer. There are endless possibilities to complete the scenario, but you're just getting the conversation going.
31. If you could start any non-profit or service project, what would it be?
32. How would you spend $1,000 extra cash?
33. What would you do if you had to live on a mountain without warning?
34. If you wrote a book, what would it be about?
35. If you became famous, how would you live your life differently?
36. If you could open any business downtown, what would it be?
37. Where would you go/live if you could travel/live anywhere?
38. What would you do if you won a major lottery?
39. If you could have the perfect marriage, what would it look like?
40. What would your ultimate retirement look like?


Some great conversations have resulted from watching a movie, then talking about how we would deal in those situations. Movies are an easy and fun way to dive into topics that we might not otherwise address (or ever face).
41. If your appearance was altered beyond recognition, how would you prove your identity to me?
42. If you were famous for something, what would you want that to be?
43. What movie/tv show best portrays the story of your life? Is it a comedy, drama, action, etc.?
44. What would you do if there was a world-wide power outage?
45. What would you do if someone stole your identity and you couldn't get it back?
46. What would you do if a couple close to you passed away and you were left to raise their child(ren)?
47. If you had to restart your life (relationships, education, etc.), where would you start?
48. What would your life be like if you said yes to everything?
49. If you were to be on a reality TV show, which one would you be on?
50. What is your favorite super hero? Which one would you want to be?

Hopes and Dreams

These should be talked about frequently. It gives us the opportunity to state our passions so we can pursue them, and helps us know our significant other's passions and find ways to support and encourage them in those. It's also good to align our goals with each other's and with God's direction.
51. If you could be paid to do anything, what would you do?
52. What would you most regret not having/doing/being in life?
53. If you had to teach something, what would you teach?
54. If money did not exist, how would you spend your days?
55. Best case scenario, where do you see yourself in 5-10 years?
56. What is your ideal home/car/career/family?
57. What are three goals you have had for over a year?
58. What is a habit you could start today that would help you reach your goals?
59. How would your life be better if you could reach your top two goals?
60. If you obtained/accomplished one major thing throughout your life, what would it be?


Talking about past memories is definitely bonding--seeing how past events have influenced them into the people they are today. However, when put on the spot, some of us aren't great at coming up with random memories, so it helps to have some questions to bring those past experiences to mind.
61. What was your favorite outfit as a kid?
62. Who was your best friend, and what was he/she like?
63. What were some of your favorite things ten years ago?
64. When you were a kid, what did you want to be when you grew up?
65. What was one of your most embarrassing moments?
66. What was one of your proudest moments?
67. Is there a scent that brings back a past memory? What is it?
68. Who was your favorite teacher?
69. When/what was your earliest memory?
70. What was your favorite family holiday?

Worst Case Scenario

These questions can be kind of a downer, so should be used sparingly and with caution. However, I wanted to include them, because talking about the tough stuff builds intimacy and can be beneficial in preparing for the unexpected.
71. If you knew you had 30 days to live, how would you spend that time?
72. If today was your last day on Earth, what would you do?
73. What would you do if you got cancer?
74. What would you do if a fire destroyed your house?
75. What would you do if a tornado came toward you while you were driving?
76. What would you do if someone broke into your home while you were there?
77. What would we want to happen to our kids if we both died in a car accident?
78. What would you do (with job, home, kids, etc.) if I died?
79. If, after an accident, you were kept alive by machines, would you want me to sign a DNR?
80. What would we do if we lost our jobs tomorrow?


Sometimes spiritual questions seem like they're meant to be left to Bible studies, but they easily have place in our daily conversations. They can be a good checkpoint for our personal faith walk, or for our faith walk as a couple/family.
81. What is your favorite/most-read book of the Bible?
82. What are times you felt closest to/furthest from God?
83. When do you remember first having a personal relationship with Christ?
84. What hymn or Christian song means the most to you?
85. Was there a spiritual mentor you looked up to when you were younger?
86. What is one thing likely getting in the way of your full potential in Christ?
87. How could we grow closer to Christ as a family?
88. Is there a major challenge we should be praying about as a family?
89. What is one thing you have learned about God this year?
90. When was the last time you saw a direct answer to prayer?

State of Being

Finally, sometimes it's just good to find out how the other person is doing. The usual "how was your day" often results in a simple "fine" or "okay." These questions can help expound and get deeper into the other person's daily life.
91. What is your daily routine like? (i.e., what is the first thing you do when you get to work?)
92. What are your favorite/least favorite parts of your day?
93. What is your most used app?
94. What is your most frequented Web site?
95. How do you prefer to take a break at the end of the day?
96. What makes you feel great about yourself?
97. When do you feel most at peace?
98. What person/place/thing inspires you the most?
99. What makes you excited?
100. What one thing could you do today that would make tomorrow better?