The first date can be one of the most nerve-wracking experiences. What can you talk about that’s not too personal? Here are 101 questions to help get your brain warmed up before meeting someone new!

The “first date questions to ask him” is a list of 101 interesting and thoughtful questions that you can ask your date. The questions are separated into categories, including the type of person you are dating, what they do for work, their favorite movie, etc.

First date: 101 interesting and thoughtful questions to ask your date


Couple on a date

With these questions, you can skip the ‘getting to know you’ stage. (Photo courtesy of Getty)

First dates may be nerve-wracking, especially if you don’t know one other.

When you’re seated across from someone and don’t know what to say, awkward silences that last just a few seconds may seem like hours.

Fortunately, has created a list of 101 thought-provoking questions to help you rekindle the conversation and discover more about your date.

We wouldn’t advocate hammering them with all of these, however, since it can seem more like an interrogation than a love date.

On a first date, what questions should you ask?

The following questions are meant to get the discussion going.

Some questions will be more relevant than others, so pick and choose carefully.

Couple chat as they walk down the street

‘How has Covid been for you?’ is a question you should avoid asking your spouse. (Photo courtesy of Getty)

  1. What is your favorite location on the planet?
  2. Which historical period would you choose if you could go back in time?
  3. Do you have any brothers or sisters?
  4. What are your working hours?
  5. When you were little, what did you want to be when you grew up?
  6. Has that objective changed, and if so, why?
  7. When it comes to relationships, do you have a ‘type’?
  8. Give an example of your dream date.
  9. What is your favorite kind of food or cuisine?
  10. What’s your favorite unusual meal pairing?
  11. Do you consume alcoholic beverages? If yes, what’s your favorite alcoholic beverage?
  12. Do I resemble the person you imagined me to be in real life? (If you met online or via a friend’s referral for a blind date)
  13. On weekends, what do you usually do?
  14. Do you have any upcoming excursions or plans?
  15. Do you have any interests outside of work?
  16. What is your all-time favorite film?
  17. What is your favorite band or musician?
  18. Who would you like to portray you in a movie about your life?
  19. Did you have a good time at school and as a kid?
  20. What is one unexpected fact about you?
  21. What’s the finest gift you’ve ever received?
  22. And what’s the finest gift you’ve ever given someone?
  23. Is there anything nice you’re reading right now?
  24. Do you have a difficult time deciding what to eat?
  25. What is the finest piece of advise you’ve ever received?
  26. Do you prefer to spend your free time resting or doing something active?
  27. Is athletics a big part of your life?
  28. Have you been alone for a long time?
  29. How are you getting on with it?
  30. What kind of pals do you have?
  31. What were you like when you were a kid or a teenager?
  32. Is there anything excellent on right now that you’re watching?
  33. Did you grow up in this area?
  34. Did you attend college or university? If so, how did you like it?
  35. What was the worst job you’ve ever had?
  36. What is your pet’s greatest pet peeve?
  37. What path did you take to get to where you are today in your career?
  38. Do you own any animals?
  39. Are you more of a cat or a dog person?
  40. What would you do with a million dollars if you won the lottery?
  41. Do you have a list of things you want to do before you die?
  42. What is your most “unpopular” viewpoint?
  43. Do you prefer the morning or the evening?
  44. Who would you be if you could be anybody for a day?
  45. What day is your birthday?
  46. Do you believe in astrology? If that’s the case, what is your zodiac sign?
  47. What is it like to live in this area?
  48. Is there anything interesting around here that I should go see? (restaurants, bars, and the like)
  49. What makes you giggle every time?
  50. Are you someone who like to plan ahead or go with the flow?
  51. Do you have a “signature dish” that you like preparing?
  52. What does relaxing look like to you?
  53. What imaginary universe would you choose to inhabit?
  54. Which is better: burgers or pizza?
  55. Do you have any core principles or convictions?
  56. What would you save if you had to save one object from your house in the event of a fire?
  57. Which ice cream flavor is your favorite?
  58. Who do you think is the most fascinating person you know?
  59. Do you have any apprehensions?
  60. What has been the most memorable day of your life?
  61. And the most difficult?
  62. What is the most bizarre thing you’ve ever done?
  63. What is your ‘happy spot,’ according to you?
  64. What was the worst date you’ve ever had?
  65. Are you a sweet or savory person?
  66. What’s the one thing you’ve always wanted to do but haven’t gotten around to?
  67. What do you believe is one feature of your personality that people notice?
  68. Which Disney film is your personal favorite?
  69. Do you have any party tricks under your sleeve?
  70. Have you ever tried out a corny chat-up line in person?
  71. What would you say to your younger self if you could convey a message?
  72. What are you most looking forward to in the future?
  73. How did you spend your time during the lockdown?
  74. Do you consider yourself to be more introverted or extroverted?
  75. Do you see the world through a half-full or half-empty lens?
  76. What luxury item would you choose if you were a contestant on I’m A Celebrity?
  77. What would you do if the world ended in one hour?
  78. Who would you bring back from the dead if you had the chance?
  79. What’s the most humiliating thing you’ve done in your life?
  80. If you were Prime Minister, what would be the first legislation you would enact?
  81. What is your guilty pleasure song, television program, or film?
  82. Have you ever fractured a bone in your body?
  83. Do you remember being a part of any’subcultures’ when you were younger? (emo, mod, indie kid, and so on)
  84. Which season is your favorite?
  85. Do you have any dating stumbling blocks?
  86. Do you believe in extraterrestrials or ghosts?
  87. Was there a separation between Ross and Rachel? (controversial!)
  88. What was your all-time favorite performance?
  89. What’s the most ridiculous item you’ve ever purchased?
  90. Which actor/band do you believe is the most overrated/underrated?
  91. What superpower would you select if you could have one?
  92. What is your ideal vacation location?
  93. Do you like being a part of a large family, being an only child, or having an older sister, for example?
  94. What animal do you believe you’d be if you were one?
  95. What kind of animal do you think I am?
  96. Is it Christmas, Halloween, New Year’s Eve, or Easter that you prefer?
  97. Who would you contact if you were arrested and thrown in jail?
  98. What is your very first memory?
  99. Have you ever left someone hanging?
  100. Do you want anything more to drink?
  101. Do you want to go out with us again?

MORE: The emergence of the ‘zero date’ — everything you need to know about the newest dating craze

MORE: A dating app for those who desire ‘kid-free relationships’ is about to start.

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The “flirty first date questions” is a book that provides 101 interesting and thoughtful questions to ask your date. It will help you get to know them better, while also making the conversation more fun.

Frequently Asked Questions

What are good questions for a first date?

A: Some questions to ask are What is your favorite color? or Do you have any siblings?

What are fun dating questions?

A: Fun dating questions are a broad category of questions that can be asked to gauge the personality, interests and habits of someone you may have romantic interest in. These types of questions typically include asking about likes, dislikes and hobbies.

What to say to keep a conversation going on a first date?

A: This is a difficult question as there are many factors that come into play. However, I would recommend trying to stay away from talking about what you do for work or where you live. Instead try asking them about their interests and hobbies!

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