Extremely & Interesting First Date Questions
Extremely & Interesting First Date Questions

Extremely & Interesting First Date Questions


A first date with someone new is likely to be awkward if the conversation seems forced or isn’t forthcoming. Though everyone looks forward to showing off their eloquence which, hopefully, will land them a second date, that is hugely dependent on the quality of questions they are able to ask their date.


Therefore, it is imperative that first date questions are gotten right in their ability to convey thoughts and in their quality as conversation starters. The first date questions below should guide you in getting the needed information about your date as well as keep your chat with them smooth. For best results, don’t ask the questions mechanically, one after the other. Rather, let them flow naturally, following the course of your conversation with your date.

First Date Questions

First Date Questions

1: Briefly describe your perfect day.

2: How often do you meet new people in your line of work?

3: What is an ideal holiday for you?

4: What do you think of work pressure, and how best can you handle it when faced with one?

5: Which book did you read recently? Can you give a brief summary of it?

6: Who is a mentor to you?

7: What makes you want to live another day?

8: Can you tell the meaning of your name?

9: Which city in the world will you give anything to visit?

10: Who is your favorite celebrity songstress?

11: Do you listen to songs from the ‘70s? Why?

12: At what level in your education did you realize the importance of a teacher?

13: When last did you visit a hospital?

14: Between staying at home every weekend and hanging out with friends in their homes, which would you rather do?

15: When last did you visit your parents?

16: If you were to choose all over, will you attend the university you finished from?

17: What is your most memorable day in high school?

18: When did you attend the best party ever?

19: Which part of the day are you most active in?

20: Who is an alcoholic to you?

21: On a scale of 0 to 10, rate your relationship with your siblings.

22: By what time is dinner best taken?

23: Do you own a radio outside the one functional in your phone?

24: Are you a TV person?

25: Do you like pets? Do you own one?

26: Have you had any reason to walk out of a seemingly good relationship?

Deep First Date Questions

Deep First Date Questions

27: What’s your take on single parenting?

28: Can you relate the politics of a country with its economy?

29: How well do you relate with your relatives?

30: When you are in danger, who do you quickly think of first?

31: What did you perceive as truth that eventually became a lie?

32: Have you lost anyone dear to you? How did you grieve them?

33: Which do you prefer: dating someone younger than you or your age mate?

34: Are you spiritual or religious?

35: Which best describes you: conservative or radical?

36: Which recent event changed your view on life?

37: Have you ever been criticized in your job? How did you handle the situation?

38: Education in the now or in the past: which one holds the most appeal to you?

39: Who taught you to read and write?

40: Can you describe your earliest memory of you and your father?

41: Which of your mother’s physical features did you inherit?

42: Has your body weight ever been a matter of concern to you? Why?

43: Sincerely, are you living out your dream?

44: Is life really short?

45: What is your own definition of untimely death?

46: Is education a means to an end or the end itself?

47: Which of your friends has proven to be your best friend?

48: Do you believe in the existence of a spirit world?

49: What are you most grateful for?

50: Have you witnessed someone dying?

51: Have you ever been in an unfortunate incident that turned out to be a blessing to you?

52: Can you paint a picture of your morning routine?

53: What is your first impression of me before we started chatting?

54: What can you equate kindness with?

55: Do you still believe in humanity? Why?

56: Which foreign cuisine have you tasted lately? Will you go back to it again and again?

Flirty First Date Questions

Flirty First Date Questions

57: Was your first kiss romantic or otherwise? Will you want it replicated or nah?

58: Which do you prefer on a first date: a full-body hug or a light kiss on your cheek?


59: In the absence of words, how do you tell someone that you are attracted to them?

60: If we were to be left alone in a room, what thoughts would spring to your mind?

61: Have you ever had sex on your first date?

62: Are you attracted to me?

63: What do you like about me?

64: Will you mind if I hold your hand in mine in public?

65: Is there anything about you that I would find difficult knowing without being told?

66: Can I make you laugh out loud?

67: Do you like the food we ordered?

68: How do you seduce someone you are fascinated with?

69: Which romantic movie do you like watching alone?

70: Has your body ever been massaged? Did you like the experience?

71: Which part of a person’s body entices you?

72: What’s your most comfortable sleeping posture?

73: If you want me to take you home, will you tell me?

74: When planning a romantic dinner with your significant other, which foods will top the list for you?

75: What’s the closest body contact you can make with a date on a first meeting?

76: Do you kiss on a first date?

77: Which part of your body is the most attractive?

78: What qualities in someone endear you to them?

79: Have you ever fallen in love on a first date?

80: In your opinion, what makes a date colorful?

81: Can you describe your worst romantic outing?

Interesting First Date Questions

Interesting First Date Questions

82: Have you ever worked from home? What circumstance led to that?

83: Between camping in your backyard and going on a vacation, which holds the most appeal to you?

84: How old were you when you first traveled by air?

85: What inspires joy in you whenever you remember it?

86: Whose opinion matters most in your home?

87: Will you choose your father again if you have to?

88: What is your skin color tone?

89: Which clothing line do you patronize often?

90: Can you define contentment in your own words?

91: What makes you fall out of love easily?

92: What’s the commonest knowledge people have of you?

93: What clothing accessory can’t you do without?

94: Which hairstyle is your most loved?

95: How many fun places have you visited in your locality recently?

96: Which animal frightens you?

97: What kind of person do you think I am?

98: What was growing up like for you?

99: What would you rather spend your day doing?

100: How fast do you learn new skills?

101: Have you ever been scammed?

102: What’s your take on dating apps?

103: What measure have you taken against a toxic person?

104: Have you been in a toxic relationship?

105: What’s your favorite snack?

106: Who taught you how to be courteous to people?

107: Which sport do you excel in doing?

108: Have you ever painted for a fee?

109: What’s the worst news you’ve ever heard?

110: Will you want to have children of your own?

111: If asked to dance, do you agree readily or hesitantly?

112: Have you ever been stranded while on a journey?

113: When was your first heartbreak?

114: What do you fear most about commitment?

115: How do you know someone is interested in you?

116: Do you visit your friends in faraway places?

117: What is the first gift you remember receiving from your mother?

118: Which work do you derive pleasure in doing?

119: How often do you ask for help from people?

120: What’s the most frustrating thing about life?

121: Is there any work you find difficult doing no matter how much you try?

Funny First Date Questions

Funny First Date Questions

122: Do you get scared when you watch horror movies?

123: Are you a people-pleaser or a hard nut to crack?

124: What will you do if there’s a fire outbreak and you had to run out in the night but you were sleeping naked?

125: What’s an unforgivable sin to you?

126: Which crime should one never be arrested for?

127: How good a liar are you?

128: What’s the color of blood?

129: Which fruit can you eat everyday and not get fed up with it?

130: Do you like my perfume?

131: Have you ever received a flying bird’s poo?

132: Do you have any regrets coming on this date with me?

133: If you have nine lives, what will you do with the ninth?


Written by Antonio Webb

Dreamer, thinker and writer who is still exploring the nuances of being a human in this world. When not writing or sleeping I keep myself busy in the aromas of the ingredients that I like to cook up for a delicious meal.