100 Great First Date Questions And Conversation Starters

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First dates are supposed to be a playful and fun way to get to know someone new. If you really want to get a guy or girl to like you, how can you learn more about them to make sure you’re interested?

Luckily, these first date questions will help you do just that.

There may be quiet or awkward times during your conversation, and that’s completely normal. Those moments give you an opportunity to look into each other’s eyes and smile. But when you’re not soul gazing, you can and should spend your time getting to know each other.

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Preparing yourself by studying up on first date conversation starters will make flirting easier and far more effective. But be sure not to plow through these questions; give them a little time to simmer, and let your date ask a series of questions, too.

Whether it’s their favorite movie or TV shows, their biggest pet peeves, or what they have on their bucket list, a good first date includes learning about one another. Plus, asking these questions will (hopefully) keep them interested enough for a second date!

100 First Date Questions

Best First Date Questions

When you’re first getting to know someone, you don’t want to come out, guns blazing. Instead, these questions will help you break the ice without prodding too far into their personal life.

1. What are some of your favorite things to do when you have free time?

2. Where is your favorite place in the world?

3. Have you ever met anyone famous?

4. Do you have any siblings?

5. Do you have any pets?

6. Are you currently binge-watching any TV shows?

7. Do you know any other languages?

8. What makes you unique?

9. If you could hang out with anyone in the world for one day, alive or dead, who would you pick?

10. Who are the special people in your life?

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Funny First Date Questions

If your date has a good sense of humor, they’ll find these questions hilarious and entertaining. These also serve as great ice breakers if the conversation has started to slow a little bit.

11. What is your most embarrassing moment?

12. What would your DJ name be?

13. What was the funniest injury you have ever had?

14. Have you ever sent a naughty text to the wrong person?

15. When was the last time you drunk texted someone?

16. What superpower would you want?

17. If someone raided your bedroom, would they be surprised by anything they find?

18. What is the weirdest fact you know?

19. What is the worst date you’ve been on?

20. What is the worst movie you’ve seen?

Flirty First Date Questions

Aside from flirting by lightly touching your date or looking into their eyes, these questions are great to ask if you’re really hitting it off!

21. Do you like to work out?

22. What is the most romantic thing you’ve ever done for someone?

23. What is your best feature?

24. What do you think my best feature is?

25. If you could take me anywhere, where would we go?

26. Are you a romantic person?

27. What excites you?

28. Are you ticklish?

29. Have you ever gotten a massage?

30. Have you ever used a pick-up line?

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Interesting First Date Questions

Once you’ve gotten past the superficial part of your date, where you get to know basic facts about each other, go a little deeper and get to know them on level, showing your interest.

31. Would you ever jump out of a plane?

32. Have you traveled much?

33. When are you the most productive?

34. What is one thing on your bucket list that you haven’t done yet?

35. Do you have a secret talent?

36. Who are your three favorite people?

37. How would you describe yourself?

38. What do you consider a fun night out?

39. What is your favorite karaoke song?

40. What is your dream car and what color would it be?

41. If you won $10,000, what is the first thing you would buy?

42. What was one of the most exciting days of your life?

Questions to Ask a Guy on a First Date

Every man is different, so this will help you get more insight into his particular quirks and interests. Then, you can determine if you have anything in common.

43. What do you look for in a woman?

44. Who is your celebrity crush?

45. How did you meet your best friend?

46. What is your proudest accomplishment?

47. Who are your favorite sports teams?

48. Who is the kindest person you know?

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49. What wrong assumptions do people make about you most often?

50. Are you into tech?

51. What skill have you always wanted to learn?

52. Who is your nemesis?

53. What three events made the biggest impact on who you are today?

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Questions to Ask a Woman on a First Date

Skip the small talk and show her you’re interested in what she has to say. Plus, these leave plenty of room for follow-up questions, letting you into her personal life a little more.

54. What is your favorite comeback?

55. What do you wish people would stop asking you?

56. What do you look for in a man?

57. What is something about you that you think will surprise me?

58. What is something that always makes you smile?

59. Do you think guys should always make the first move?

60. What is the most expensive thing you ever bought?

61. How often do you see your friends?

62. What is your best friend like?

63. Do you sing in the car or shower?

64. What is in your pockets right now?

Deep First Date Questions

These questions are intellectually stimulating, and your date will have to do some thinking before answering. It’s a good indicator of whether or not they can be philosophical and look a little deeper into themselves?

65. What is your favorite childhood memory?

66. If you could work anywhere in the world, where would it be?

67. What is your deepest fear?

68. What do you appreciate more, physical touch or getting a gift?

69. What is your favorite quote?

70. What do you think you’ll be doing when you’re 85?

71. What is the hardest thing you’ve ever done in life?

72. Who was your most significant role model?

73. Is there a smell that always reminds you of good memories?

74. What are you good at?

75. What makes you happy?

76. How would your friends describe you?

77. What is the best present you gave someone?

78. What were you like as a kid?

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Important First Date Questions

When you ask these questions, you’re getting a better look into your date’s life and personality, their values, what they want in the future, and what that means in regards to your personal preferences and needs.

79. How do you relax?

80. How many online dates have you been on?

81. When would you want to retire?

82. Where do you see yourself in 10 years?

83. Do you want children?

84. What do you do on the weekends?

85. What were you like as a kid?

86. Do you trust your gut, or go with the flow?

87. What is your most valuable possession?

88. What is your biggest passion?

89. What is your biggest pet peeve?

90. How much alone time do you tend to need?

91. Where did you grow up?

Awkward First Date Questions to Avoid

There are topics of conversation that should be off-limits, including your date’s past dating life, their family, and money. Be sure to stick to questions that don’t cause uncomfortable silences.

92. How much money do you make?

93. How soon do you want to get married?

94. What is the shadiest thing you've ever done?

95. Why are you single?

96. Why did your last relationship end?

97. Are you close with your parents?

98. How long have you been single?

99. Have you ever been arrested?

100. How often do you talk to your best friend?

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Dina Colada is an author, speaker and dating coach who specializes in helping single women navigate the modern world of online dating. Her work has appeared on sites like Prevention, MSN, Women’s Health, Plenty of Fish and Zoosk. Visit her website for more.

This article was originally published at Dina Colada. Reprinted with permission from the author.