149 Date Night Questions: Easy, Fun & Deep

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Imagine your ideal date- what comes to mind? 

Maybe it’s a romantic dinner for two, a leisurely stroll through a park, or a spontaneous night of activities.

Whatever your idea of the perfect date may be, one thing is for sure: a great conversation is a must-have.

There’s nothing quite like the thrill of getting lost in talks that flows effortlessly from one topic to the next, laughing and learning more about each other with every passing moment.

To help you get started, we compiled a good list of thought-provoking, enjoyable, and fun date night questions you can use to spark some interesting discussions and discover new things about your potential partner or special someone.

From favorite foods and music to inspirations and thoughts about life, these questions are sure to keep you connected and entertained.

So, if you’re ready to add a little sparkle during your lovely time with each other, let’s get started.

You may also like our 163 Second Date Questions, 101 Fun Questions For Couples, and 161 Anniversary Questions for Couples.

Easy Date Night Questions

If you’re on the hunt for some conversation-starters that won’t make you feel like you’re in the hot seat, let’s kick things off with some easy date night questions that will help you get to know your special someone in a comfortable, low-pressure way.

These questions are the perfect balance of fun and lightheartedness, without delving too deep into heavy topics. 

1. Do you have a best friend?

2. Have you lived in another country?

3. What hobbies do you have?

4. What is your favorite food?

5. What do you drink in the morning after waking up?

6. Who is your favorite musician?

7. What is a band or song you can’t stand?

8. What do you consider to be your strongest skill?

9. When you were younger, what did you want to be when you grew up?

10. What would you do if you won a large sum of money?

11. What is your favorite quote?

12. Do you have somewhere that you like to take your dates?

13. If money wasn’t an issue, what would you do for work?

14. Do you have a movie that you like to watch over and over again?

15. Do you have any superstitions?

16. What is something you wish you never had to do again?

17. Have you been in trouble with the law before?

18. Who is someone that you look up to?

19. What is something you enjoy doing in your free time?

20. What is something you wish you had more time to do?

21. Have you ever tried to cook for fun?

For more couple date night questions, check our list of romantic discussion topics for partners.

Diverse gay couple cooking in the kitchen.

Date Night Questions to Ask a Man

Get ready to ask away and discover all the wonderful things that make your guy special!

Whether you’re looking for a light conversation starter or a deep dive into your man’s psyche, these great date night questions are the perfect tool for getting to know him better.

22. What is something you find irresistible in a partner?

23. If you had any superpower, what would it be?

24. What is the corniest joke you know?

25. What is the worst advice you have ever been given?

26. Do you plan out your day in a daily planner?

27. What is something about you that most people would never guess?

28. What is one of the first things you notice about a person?

29. What pick-up line have you used in the past that has worked?

30. Do you think opposites attract when it comes to romance?

31. Have you ever had your heart broken?

32. What is one word you would use to describe yourself?

33. Where do you see yourself in ten years?

34. Do you feel comfortable when people ask a lot of questions about you?

35. Do you know your love language?

36. Are you living a life you are proud of?

Looking for married date night questions? Check this guide

You may also try our list of open-ended questions to ask a guy.

Man stretching and yawning on laptop.

Date Night Questions to Ask a Women

Looking to woo the woman of your dreams and create a date night to remember?

With our list of perfect date night questions below, get ready to charm, engage, and maybe even learn a thing or two about the woman across the table from you.

37. What is something that a partner can do to make you feel loved and appreciated?

39. What is the greatest advice you have ever been given? 

38. How fulfilled do you feel in your life?

40. How do you think other people would describe you?

41. Where do you see yourself in five years?

42. Have you broken someone’s heart in the past?

43. Is there something that people tend to assume about you that isn’t true?

44. What is something that always makes you smile?

45. What is your favorite scent?

46. What does the perfect date look like to you?

47. What is something you are always up for doing?

48. What is something you do every day to help your day go smoother?

49. Is there a celebrity you think you would be friends with if given a chance?

50. Do you like to try new things?

You may also like our list of date night questions for married couples.

Girl Paddling on the Buffalo River Arkansas.

Yes or No Date Night Questions

To make your conversations exciting, there’s no need to start things off with lengthy chats- in fact, a simple date night questions game will do.

Try our list of yes or no questions below to explore everything from wacky hypothetical scenarios to unexpected revelations about your date’s personality. 

Who knows what you might learn about each other along the way?

51. Do you like to exercise?

52. Do you like dogs?

53. Do you like cats?

54. Do you like kids?

55. Do you think you are funny?

56. Have you been to another country?

57. Do you know how to skip rope?

58. Have you cried during a movie?

59. Do you have a nickname?

60. Do you enjoy theme parks?

61. Are you afraid of heights?

62. Do you like playing video games?

63. Do you spend a lot of time scrolling social media?

64. Are you quick to apologize when you are wrong?

65. Would you go out to a public place dressed in matching outfits?

66. Do you think telling white lies is ok in a relationship?

67. Are you an adventurous person?

68. Do you have a curious mind?

69. Can you be spontaneous?

70. Do you ever let dishes pile up in your kitchen sink?

71. Do you like where you are in life right now?

72. Do you want children in the future?

73. Are you ready to settle down into a relationship?

74. If given a chance, would you go to Mars?

75. Do you like to eat breakfast?

76. Have I ever given you butterflies in your stomach?

77. Do you think I am a good listener?

78. Do you like to cuddle?

79. Do I make you feel special?

80. Do you like public displays of affection?

81. Do you enjoy spending time alone?

82. Do you think you would make a good parent?

83. If you had enough money, would you help out your family financially?

84. Have you ever broken one of your bones?

85. Have you been in a car accident?

86. Have you sung karaoke before? What about any of these duets?

You may also like our list of yes or no questions for couples.

Friends having fun with a man holding a microphone and tablet.

Would You Rather Date Night Questions

Another entertaining way to learn more about your partner’s preferences, values, and even sense of humor is by asking would you rather questions.

Not only does this game help break the ice and keep the conversation light, but it also offers insight into your date’s personality and what makes them tick. 

87. Would you rather live in the country or the city?

88. Would you rather go to a sporting event or see a play?

89. Would you rather stay in for the night watching movies or dance the night away at a club?

90. Would you rather get up early in the morning or stay up late at night?

91. Would you rather win a million dollars or have perfect health for the rest of your life?

92. Would you rather read a book or watch a movie?

93. Would you rather time travel ten years into the past or ten years into the future?

94. Would you rather have a tropical vacation or a mountain getaway?

95. Would you rather eat pizza or tacos?

97. Would you rather go for a scenic hike or go out partying all night?

98. Would you rather give money to a charity or give money directly to a homeless person?

99. Would you rather watch a horror movie or a comedy?

100. Would you rather go for dinner in a restaurant or a picnic in the park?

101. Would you rather go for a long walk or a long drive?

102. Would you rather try new foods or eat comfort foods?

103. Would you rather work out together or get a couples massage?

104. Would you rather spend the day in a hot air balloon or on a sailboat?

105. Would you rather receive an embarrassing text message or a scary voicemail?

106. Would you rather binge on chocolate or ice cream?

107. Would you rather sit around a campfire or a fireplace?

108. Would you rather sit in a hot tub with me or a sauna?

109. Would you rather have me give you a neck rub or a foot rub?

110. Would you rather get a puppy or a kitten together?

111. Would you rather take pictures in matching pajamas or matching outfits?

112. Would you rather receive a bouquet of flowers or balloons?

113. Would you rather take a hot or cold shower?

114. Would you rather make the first move on a date or let the other person make the first move?

115. Would you rather get a kiss on the cheek or on the forehead?

116. Would you rather tell someone how you feel through a text message or in person?

117. Would you rather receive an expensive gift or a sentimental gift?

118. Would you rather give me a nickname only we know or one we use in front of other people?

119. Would you rather kiss me in front of your friends or in front of your family?

110. Would you rather lie to someone to protect their feelings or be honest and hurt their feelings?

111. Would you rather have an endless supply of money or infinite happiness?

112. Would you rather have your partner be good in bed or a good cook?

113. Would you rather go to an escape room or a museum for a date night?

114. Would you rather have me cut your hair or have access to your social media for 24 hours?

115. Would you rather be able to change something in your past or predict your future?

116. Would you rather eat sushi or strawberries?

117. Would you rather be an expert at something or average at a bunch of things?

118. Would you rather drink tea or drink coffee?

You can also check out our list of would you rather questions for couples.

Coffee on table with books.

Deep Date Night Questions

Sure, small talk has its place, but when you’re looking to make a lasting impression, you need to dig a little deeper

By asking thought-provoking questions that delve into your date’s passions, fears, and dreams, you’ll uncover a whole new side of them that you may have never seen before. 

You can also use the following as spouse date night questions since some topics work best for married couples.

119. Have you found your purpose?

120. Do you have anything you are passionate about?

121. Have you protested something before?

122. What is the kindest gesture anyone has done for you?

123. What is a smell that reminds you of your childhood?

124. What does your perfect day look like?

125. What is a talent that you wish you had?

126. What do you believe is your best feature?

127. If we could take a vacation together and money wasn’t an issue, where would we go and what would we do?

128. What is something in your life that you are so grateful for?

129. What is your relationship status with your parents?

130. Are you generally happy?

131. What is your biggest fear?

132. What is your biggest regret?

133. Do you think either of us has changed since we started dating, if yes, how have we changed?

134. What is your favorite moment that we have had together?

135. Who would you call first if you had a big decision to make?

136. Do you think it is possible just to be friends with an ex?

137. What is a good way to cheer you up when you are feeling down?

138. What was one of the most challenging times in your life?

139. What do you feel is more important in a relationship, a physical or emotional connection?

140. How do you want a friend to support you when you have problems?

141. Do you have deal breakers when it comes to relationships?

142. If you could go back to school for anything, what would you take?

143. What do you like the most about yourself?

144. What is something that inspires you?

145. When are you the happiest?

146. What do you feel I have helped you with during our relationship?

147. Do you think the tough times in our relationship have brought us closer?

148. Do you feel safe with me?

149. Is there something I can do to make you feel more loved in our relationship?

You may also like our list of funny first date questions.

Mixed Race Couple Hugging and Standing While Laughing.

Final Thoughts

So the next time you’re planning a date night, consider trying out some of these questions and see where the conversation takes you.

If you tried any of these topics on a date night before, we would love to hear your experiences, so feel free to share your thoughts in the comments below! 

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