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99 Questions to Ask on a First Date

Feb 06 2018 Avatar for Cassi VillanuevaBy Cassi Villanueva
99 Questions to Ask on a First Date

Have you ever been asked a question so embarrassing it made you blush? Or one that made you laugh so much your cheeks hurt?

When you’re exploring dating sites, it can be daunting to think about what you’ll talk about on your first date. But these conversations can lead to amazing relationships — and can really help you get to know the other person!

No Leading. No Promising. No Interrupting.

No Leading. No Promising. No Interrupting

My husband and I both come from youth ministry backgrounds so it was no surprise that when we first began dating, playing the question game was par for the course. “The Question Game” as one of my core members long ago called it, is where you ask a person a question, they answer it, and then return a different question to you.

The funny thing we learned as we journeyed through ministry with teenagers was that as much as they loved the questions, we adults probably enjoyed them more. When a conversation falls silent or you’re just getting to know a person who you just met on a dating site, nothing breaks the ice like a good old-fashioned game of question ping pong.

“So, I can spend an entire date asking questions?” Well, if that’s your prerogative, sure! But honestly, you can ask as many or as few as you want. Often when my husband and I play (yes, after 14 years of marriage we still play the question game regularly), eventually we will land on a question that leads into a longer, deeper conversation.

Why Questions?

Why Questions?

    • They are direct and to the point.
    • They provide an intro to a conversation that hasn’t been started.
    • They help break the awkwardness of a first date.
    • They provide you an opportunity to begin getting to know a person right away.
    • They make you think about things you that may not have crossed your mind before.

    As you’ll find once you begin asking questions, there will never be a shortage. Sure, it’s easy to blank on new ones sometimes, but they’re out there (or shall I say, in there …).

    Silly and serious ones, deep and not so deep. Just use your imagination and have fun with it. (And know that anyone who’s on a dating site probably has the same worries as you!)

     

    Because I solemnly swear by the question game, I’m not going to leave you hanging. I’ll get you started by giving you a variety of questions to ask on your first date—99 in fact!

 Good Conversation Starters

Good Conversation Starters

1. Where did you grow up?

2. What did you study in college?

3. How many siblings do you have?

4. Are you a coffee or tea person?

5. What’s your favorite season?

6. Do you have a favorite sport to play?

7. What’s your favorite sport to watch?

8. What are some of your hobbies?

9. Are you a paperback, Kindle or book on CD kind of person?

10. What is your temperament/personality type?

11. What’s your favorite food?

12. Are you better at English or Math?

13. Do you like camping?

14. What’s your default category on Netflix?

15. What’s one of your favorite go-to snacks?

16. Who’s your favorite saint?

17. Are you a gym rat or a couch potato? Somewhere in between?

18. What’s the craziest thing you’ve ever done?

19. Apple or Android?

20. Chocolate or vanilla?

Serious/Deep Questions

Serious/Deep Questions

21. If you could live anywhere in the world, money not an issue, where would it be and why?

22. What is your biggest fear?

23. If you could have a meeting with our current president, what issues would you discuss?

24. What do you imagine yourself doing 5 years from now?

25. If you could go back into the past and change one event, what would it be?

26. If you were offered the ability to use mind control, would you accept it? Why/why not?

27. If you woke up to the news that a meteor was going to destroy the earth in 10 days, what would you do?

28. If you wrote a book about a topic that is very personal to you, what would the title be?

29. Which of the 7 Deadly Sins do you struggle with the most?

30. Describe your worst nightmare … in detail.

31. What is something your future spouse absolutely has to possess?

32. What’s something you’d like to ask me but are nervous to?

33. If you could change one physical thing about yourself, what would it be?

34. If you could change one thing about your personality/temperament, what would it be?

35. If you could have a better relationship with one of your family members, who would it be?

36. Have you ever been in trouble with the law?

37. If you could cure any disease, what would it be?

Funny conversation starters

Funny conversation starters

38. If you had to choose between being perpetually smelly (even after showering) or covered head to toe in hair that would grow back the minute you shaved, which would you choose?

39. Would you rather be born with a tail or a third eye?

40. If reincarnation were real, would you rather come back as a cat or a dog?

41. If you were a cat, would you be the kind that loves people or the antisocial hide under the bed type?

42. What is the strangest thing about you?

43. If you could only eat pizza or hamburgers for the rest of your life, which would you choose?

44. What is your idea of the ultimate practical joke?

45. If you could choose any superpower, what would it be?

46. Would you rather have rainbow colored teeth or hair?

47. If you HAD to donate a body part, what would it be?

48. Would you rather the weather be perpetually sunny or snowy?

49. Where are you the most ticklish?

50. If you had to wear the same outfit every day for the rest of your life, what would it be?

51. What kind of pajamas do you wear?

52. If you could have the world’s greatest legs or greatest singing voice, which would you choose?

53. If you had to be a color of the rainbow, which color would you be?

54. If you had to own either a snake or a skunk which would you choose?

55. Do you have any funny human tricks you can do (double-jointed, tongue-to-nose, etc)?

56. Would you rather be covered with snakes or roaches?

57. Pick your apocalypse—zombie or nuclear?

Personal questions

Personal questions

58. What is something you would like to see change in the world?

59. What would you consider to be one of your greatest talents?

60. Have you ever been hurt by someone so bad that you still have a hard time forgiving them?

61. What do you struggle with the most when it comes to the Catholic faith?

62. What is your idea of the perfect date night?

63. Are you a pretty trusting person or does it take you a while to let people in? Why?

64. What person has made the biggest impact on your life?

65. If you could choose your future number of children, how many would you have?

66. Which member of your family are you closest to and why?

67. What is your biggest dream?

68. In what capacity do you like to serve others (soup kitchen, donations, help babysit, etc.)?

69. Is there a side to you that you don’t often let others see?

70. You’re on a plane and suddenly the captain announces that you’re going to crash. What is the first thing you do?

71. What is your favorite holiday?

72. Do you believe religion and politics to be good talking points, or things that should be private?

73. Who do you wish was still alive today?

74. What’s your favorite thing about your face?

75. How many speeding tickets or traffic citations have you received?

76. Do you have a hero? Who?

77. Have you ever had surgery?

Random conversation starters

Random conversation starters

78. If you were ever given the opportunity to travel to space, would you accept it?

79. What is the nicest thing someone not related to you, has ever done for you?

80. If you could be best friends with any tv character, who would it be?

81. What was your favorite childhood cartoon?

82. Have you ever read a book that made you cry?

83. If you could choose an instrument to suddenly be amazingly proficient at, which would it be?

84. If you could be the world’s best athlete, what sport would you play?

85. Would you ever run for public office?

86. What was your least favorite subject in school?

87. Are you a real or artificial Christmas tree kind of person?

88. What’s a pet peeve of yours?

89. Would you rather skydive or go caving?

90. What is something on your bucket list that would surprise people?

91. If you could meet anyone, living or deceased, who would it be and why?

92. If you were a teacher, what grade would you choose to teach?

93. Do you prefer sweet or salty foods?

94. If you could travel back in time, what era would you choose to land in?

95. If you could take someone’s place as the lead role in a movie or show, who and what would it be?

96. Do you prefer the beach or the mountains?

97. Pick your poison—wine, beer or tequila?

98. Which is scarier, an earthquake or a tornado?

99. Would you like to go on a second date?

Meeting someone from a faith-based online dating site can be fun and exciting. With the right questions, you’ll have fun learning all about them!

Avatar for Cassi Villanueva

Cassi Villanueva is a freelance writer and contributing blogger at Catholic Singles. Born and raised in the south, when she's not writing, she can be found spending time with her husband and four children in the northern suburbs of Atlanta, GA.

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