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101 Unique Questions to Ask on a First Date


A first date can be a nerve wracking experience and there is nothing worse than running out of things to talk about. In this article, I will outline 101 unique open questions which will spark fantastic conversation with a woman and allow for hours of conversation. Use this article as a cheat sheet whilst on a date, if necessary.

To have a great conversation you often have to ask an open question and then follow up to the other person's response with statements. Try not to ask a reel of questions. Instead, ask a question; listen to their response and then say your own opinion.


Below are 101 unique questions which will spark a woman's emotions and allow for vibrant conversation on a first date:

1) What excites you about (insert city in which you live)?

2) If today was the last day of your life, how would you spend it?

3) What impact do you want to leave the world?

4) Would you rather be less attractive and rich or extremely attractive and poor?

5) Would you break the law to save a family member?

6) What type of guy are you attracted to?

7) Which song makes you feel amazing and why?

8) What is the most romantic experience you have ever had?

9) Would you rather have true love or win the lottery?

10) Favourite childhood animated movie?

11) Describe your best holiday experience in your life.

12) If you could visit any country in the world, which would you visit and why?

13) What was your childhood fear?

14) How would you spent 10 million pounds?

15) If your boyfriend cheated on you, would you slap him or cheat on him?

16) Can you describe your greatest fantasy?

17) What was the weirdest relationship you have ever had?

18) If I was an ice cream, how would you eat me?

19) How close are you to your family?

20) What makes you smile in life?

21) What is your favourite ice cream flavour and why?

22) Who was your first crush?

23) What are your ideas about true love?

24) What's your favourite colour? 

25) Describe the most embarassing moment in your life?

26) What's the habit you're proudest of breaking?

27) What was your funniest moment in your life?

28) If you ruled the world, what would your change?

29) Who's the person in your life that you admire most, and why?

 Do you like spontaneity or do you like routine?

31) Tell me about your friends?

32) Is there anything you're really passionate about?

33) Do you believe in love at first sight?

34) Can you describe your dream house to me?

35) Are there any causes you strongly believe in?

36) 3 physical features you get complimented on a lot?

37) Can you describe your first kiss?

38) Give the names of 3 things you dislike most and why?

39) What's the worst injury you've ever had?

Do you have any pet names? If yes, how did you get them?

41) Do you believe that the cup is half empty or half full?

42) Do you remeber who taught you to ride a bike?

43) Can you describe the craziest thing you have ever done?

44) Favourite film star?

45) How do you like to spend New Year's Eve?

46) Describe your relationship with your parents?

47) Favourite day of the week?

48) Do you have any bad habits?

49) Do you consider yourself sexually open minded?

50) How do you feel about porn?

51) What is your biggest goal in life?

52) How would your friends describe you in three words?

53) Have you ever experimented with drugs?

54) Which living celebrity would you like to know?

55) If you could invite any three people from history to dinner, who would you invite?

56) Do you have a favourite film?

57) What is the most courageous thing you have ever done in your life?

58) What is your earliest memory?

59) If you had three wishes, what would you wish for?

60) If you could have a superpower, what would be your superpower?

61) What is the best advice you have ever received?

62) Who was your hottest boyfriend?

63) Has a guy ever asked to marry you?

64) Have you ever kissed a girl?

Ever been in a catfight? Who scratched who?

Can you fake any accent? If yes, would you show me?

67) If you had one day in your life to live over again, which would you choose and why?

68) If your house was on fire and you could save one possession, what would you save?

69) How often do you talk to your parents?

 Favourite quote in life?

71) If you could speak one language, what would it be and why?

72) If you had your own country, what would be some of the rules?

73) What is your favourite four letter word and why?

74) If you had a label round your neck, what would it say?

75) What was the last nice thing your dad did for your mum?

 How many times have you lost your mobile, and were there any interesting ways?

77) American pancakes or English (flat) pancakes?

78) Put your iTunes on shuffle. Give me the first 6 songs that pop up.

79) How do you vent your anger?

80) How would you define art?

81) What is your astrological sign?

82) What would be a question you'd be afraid to tell the truth on?

83) In your opinion, what makes a great relationship?

84) What is your ethnic background?

85) Do you save money or spend it?

86) Ever had a rumour spread about you?

87) If you could change your natural hair colour, would you?
 To what?

88) Coolest thing you have ever been for Halloween?

89) Pirates or ninjas?

90) What kind of smoothie sounds really good right now?

91) Do you prefer to wake up early or stay in bed till late in the morning?

Ever tried online dating? Worst experience?

93) What is your favourite way to spend a Saturday?

94) Where do you see yourself 10 years from now?

95) If your life were a book, what would you name it?

96) Beach holiday or sightseeing holiday? Why?

97) Would you prefer an exotic meal in a five-star hotel or a delicious chocolate-cake from a local bakery?

98) Do you believe in God?

99) How many kids would you like to have? 

100) What turns you off the most?

101) Did you ever have a crush on a male teacher?

I hope this guide will help you on your first dates. I suggest using this as a cheat sheet on your phone.
 If you enjoyed this, check out my other blog entries or other RSD articles.

Best of luck.



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