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100 First Date Questions to Start a Conversation

Updated on May 23, 2018

A first date can be rather unnerving. No matter how confident you are of yourself you still feel the nerves when you go on your first date. Everybody wants their first date to be a memorable; however for many the first date turns a rather forgettable experience. Individuals that go on a first date are clueless about how things are going to unfold, and rightly so. On your first date you want everything to be perfect. You want to have a conversation with your date, but fail miserably. Why does this happen? A romantic date is likely to be a dampener if you ask the wrong questions. On a first date, both men and women seem confused about how to start a conversation.


What questions help start a meaningful conversation

A question that weighs heavily on a person’s mind when he/she is going on a first date is… What should I talk about? When this question pops up in the head you are likely to feel the butterflies flutter in your stomach as you get nervous. Thoughts about what you are going to talk on your first date can cause havoc. Try and remain calm before your date. Do not think about what will happen on your date. Instead, just be positive and approach the big day like any other. A great way to start a conversation on a first date is with questions. Meaningful conversations stem from meaningful questions. A wise way to open up with your date and get rid of nerves is by asking appropriate questions. However, many of us do irreparable damage by asking wrong questions while on a romantic first date.


While a fair share believe its men that commit the common mistake of asking wrong questions on a first date, the truth is both men and women get it wrong with questions. Keep in mind, questions asked can make a first date momentous or disastrous, so be careful with the questions you ask. In a bid to try and break the ice, individuals try and get too personal, and this aspect is a major put off. Personal questions should be avoided on your first date. Be wise with your questions, discussions and conversations. On many first dates, one individual may go on talking and asking questions without allowing the other to speak, this should not happen.


First Date Questions- Do’s and Don’ts

The first thing you need to do is ensure your date is comfortable. Do not bombard your date with complicated questions, if this works, it will only be against you. The best way to build a bridge for a conversation is with a simple question. First date questions should be interesting and engaging conversation starters. Furthermore, be a good listener on your first date. On a romantic date you need to be open to varied possibilities. The fact that you are on a date says you are eager to know the person, or interested in the person. Good questions help ease the way for a solid conversation. Share experiences, childhood memories, goals, and aims with each other, it’s a great way to make each other feel comfortable. Do not feel shy to talk about mistakes you have made or lessons you have learned from life. Talk about your achievements, but do not brag. As you converse you invariably find your comfort zone.

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Keep the following in mind on your first date

  • Be sensitive in your approach.
  • Do not ask your date about his/her ex.
  • Do not be too nosy with your questions.
  • Do not ask inappropriate questions or objectionable questions.
  • Do not dig into your date’s past. You are not here to scrutinize you date’s dating history.
  • Do not go on talking; give your date a chance to talk.
  • Be a good listener.
  • Frame your questions wisely. Remember you are on a date and not an interviewer at an interview.
  • When you expect answers to questions you ask, also be prepared to answer questions that come your way.
  • Make sure you ask questions that help engage in a conversation.
  • Do not ask too many questions.
  • If you feel like you are out of things to talk about, it’s wise to excuse yourself and head to the washroom for quick enlightenment and then get back with a meaningful question.
  • Be thoughtful with your opinion but do not be overly opinionated.

As the date progresses with the conversations you have, you will be able to able to gauge whether your date is showing keen interest to take this forward towards a serious relationship or just looking at spending an evening with you. Your approach says it all on a date. Do not be hasty; take it a step at a time with your approach. Most important…Be You! Simple and meaningful questions you ask on a first date pave the way for a great conversation.

The lines below showcase a list of questions you can use in your approach on a romantic date.


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Once you get comfortable with your date it is natural that you want to learn more about him/her. Do not touch upon sensitive issues. You will be curious to know whether your date has had any romantic experiences in the past or whether he/she has been in a relationship with someone, or aspects about their dating experience. You cannot ask your date bluntly about what you seek to know. You have to be careful with your approach pertaining to a sensitive topic or subject which is personal. A wise way to get to know more about your date’s personal life is by being a little naughty and funny in the course of the conversation and casually putting forth a question. At this point it’s important for you to observe your date’s body language. You will immediately be able to tell if your date is comfortable answering your question. Depending on how your date reacts and responds, decide spontaneously whether you want to dwell deeper with serious questions.


100 First Date Questions to Start a Conversation

  1. So, Tell Me about yourself, where did you grow up?
  2. What do you like doing in your free time?
  3. What makes you laugh?
  4. What are your hobbies?
  5. Tell me about your family…do you have siblings?
  6. Have you always lived in this city/state?
  7. Do you have a pet name? How did you get your pet name?
  8. What music do you like listening to?
  9. Do you like pets?
  10. Do you like reading, what type of books do you like reading?
  11. Where did you do your schooling or which college did you attend?
  12. What movies do you like watching?
  13. What’s your favorite childhood memory?
  14. What’s your favorite song?
  15. What’s your idea of a perfect vacation?
  16. Are you a morning person or a night person?
  17. Are you more of an indoor or outdoor person?
  18. Is there something you want to change in this world?
  19. What’s your most cherished moment with family?
  20. Who was your first crush?
  21. What’s the craziest thing you have done?
  22. What’s your most cherished moment with friends?
  23. How much have you changed since school?
  24. What is your favorite food?
  25. What is the most beautiful view you have come across?
  26. What would be your dream job?
  27. A movie or TV show you like to watch over and over again?
  28. Are you obsessed about anything?
  29. How is your Sunday like?
  30. Is there an interesting fact you are aware of that the world needs to know?
  31. Do you like adventure trips?
  32. What’s your zodiac sign?
  33. What was the last party you attended?
  34. Where do you like to hang out with friends?
  35. What’s your biggest regret in life?
  36. When was the last time you walked for more than an hour?
  37. What is your favorite sport?
  38. What’s your best way to unwind?
  39. When was the last time you sang to yourself of someone?
  40. What did you Google last?
  41. Is there something you want to try at least once?
  42. Who is the kindest person you have known?
  43. What was something you did recently for the first time and really enjoyed?
  44. What is your idea of a relaxing situation?
  45. What do you fear most?
  46. Something you would be willing to pay any price?
  47. Something you like to keep yourself updated often, continually, or constantly?
  48. An odd talent you have nobody knows about?
  49. What’s your best ice cream flavor and worst ice cream flavor?
  50. What’s the best thing that has happened to you this year?
  51. What did you do last summer?
  52. What’s the worst pickup line someone has tried on you?
  53. Has something had a significant impact on your life?
  54. What is the best pickup line you have heard?
  55. Do you like gadgets, what’s your favorite gadget?
  56. What’s your favorite everyday activity and you most boring everyday activity?
  57. What’s your idea of a perfect romantic date?
  58. What are you most grateful for?
  59. Do you like texting on the cellphone or talking on the cellphone?
  60. Do you sing or hum while taking a shower?
  61. A restaurant you love going often and why?
  62. When do you feel out of place?
  63. What’s on your bucket list?
  64. Chinese Food or Italian food and why?
  65. A fad you never really understood or cared for?
  66. What’s your favorite non-alcoholic and alcoholic drink?
  67. Have you been on a blind date?
  68. What’s your favorite television show?
  69. Any accomplishments you are proud of?
  70. Do you prefer to work as a team or alone?
  71. Do you like going shopping?
  72. Have you been misunderstood by people?
  73. If you had a lot of money would you still work?
  74. Do you get easily irritated?
  75. If you could give one piece of advice to the world what would it be?
  76. What’s the app you use often on your phone?
  77. Would you like to be famous, if yes what would you want to be famous for, if no, why not?
  78. A strange place you have been to?
  79. Which animal do you find cute and why?
  80. You favorite area at home?
  81. Who is your favorite actor/actress?
  82. Before buying something do you read reviews or just go with your gut feeling?
  83. What do you find most attractive in a man/woman?
  84. What’s the strangest conversation you have ever had?
  85. Something you are always game for?
  86. What do you do on weekends?
  87. Who are the 4 most important people in your life?
  88. What’s a trend you swear by?
  89. Do you like travelling?
  90. Anything you would like to change about yourself?
  91. What’s your perfect Morning?
  92. Your favorite band/singer?
  93. Who is your favorite author?
  94. Have you had a forgettable experience on a date?
  95. Has anybody made a pass at you? How did you react?
  96. Is there a city you want to live in?
  97. What’s your favorite piece of furniture?
  98. Did you have a crush on someone in school or college?
  99. What qualities do you look for in a person and what qualities do you dislike in a person?
  100. What are your ambitions?

More Questions to ask on a First Date to Start a Conversation

  • Have you got bored at a family party?
  • Is there something you like but are embarrassed to admit?
  • What are you passionate about?
  • If you could be any person for a day who would it be?
  • What’s your most valuable possession?
  • Do you feel nervous when you are out of your comfort zone?
  • What’s your favorite line from a song?
  • What’s your favorite line from a movie?
  • What’s your daily schedule like?
  • Something that took you a long time to figure out?
  • What do you miss about life 15 years ago?
  • Is there a place you like to visit regularly?
  • What’s your biggest pet peeve?
  • Do you like playing video games, what’s your favorite game?
  • How important is planning in your life?
  • Are you a career driven person?
  • A habit you want to cultivate?
  • What’s the most ridiculous thing you have done when you were bored?
  • If you could eat just one thing for the rest of your life, what would that be?
  • What do you care less about?
  • What band are you listening to right now?
  • What are you favorite toppings on a pizza or burger?
  • Where do you see yourself 10 years from now?
  • What’s your guilty pleasure?
  • What’s the best way to get to know someone?
  • What is your favorite holiday destination?
  • With whom do you enjoy having a phone conversation with and why?
  • An appliance at home you just cannot do without?
  • If you were given an opportunity to start a business what business would you start, and why?
  • What smell/s do you like?
  • Are you a social media person?
  • What’s been a turning point in your life?
  • Do you have a favorite quote or saying?
  • How important is money in a relationship?
  • Is there something from childhood you would love to have in adulthood?
  • What’s your favorite Holiday tradition?
  • Have you had a nickname you didn’t like?
  • What do you never get tired of?
  • What’s the most spontaneous thing you have done?
  • Besides home and your workplace where do you spend most of your time?
  • What do you talk about often?
  • Something that is not required that you carry in your purse/wallet?
  • Do you prefer taking the train or the bus and why?
  • What’s the hardest thing you have done?
  • What social situation/s do you try and avoid often?
  • What the best thing and worst thing about getting older?
  • Are you scared of insects or anything else?
  • What do you do differently than most people?
  • What’s your social life like?
  • Have you played a prank on anyone or has anyone played a prank on you?
  • Is there something you’ve always wanted to learn but haven’t?
  • A household chore you enjoy doing and why?
  • What movie did you see last?
  • Do you prefer Saturday Nights or Sunday Mornings?
  • Who is the most bizarre person you have met?
  • Do you prefer tea or coffee and why?
  • Besides your parents, who taught you most in life?
  • Do you like to dance?
  • What’s the best thing and worst thing about being grown up?
  • What’s the worst advice you have received from someone?
  • What’s the cheesiest song you love listening to?
  • What’s in your refrigerator right now?
  • What’s the best meal you have had recently?
  • What says a lot about a person?

© 2018 Ansel Pereira


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