201 Questions for a First Date: Only The Best Questions!

  • Home
  • /
  • Charisma
  • /
  • 201 Questions for a First Date: Only The Best Questions!

Getting good questions for a first date is crucial because it helps you break the ice and connect with your new potential partner!

In this post I’ll give you the best questions so that you don’t end up sounding like an interrogator!

You’ll find great questions that easily trump the classic “what do you do?” question. From now on you won’t sound like an interviewer.

By the way, the more relaxed you feel, the better questions you’ll ask so don’t hesitate to get a couple drinks for yourself!

Anyways, let’s get started!

Questions for a first date from Reddit

  1. What is your family like?
  2. What has been the best part of this year?
  3. Are you an introvert or an extrovert?
  4. Do you think money makes the world go around?
  5. Do you like tattoos?
  6. If you won the lottery, what would you do with the money?
  7. What is the best thing about your personality?

Although these may be Interesting questions for a first date, I don’t like them because they are not open-ended. I.e. they are yes or no questions.

These are better (also from Reddit):

  • Are you a cat person or dog person? I mean, if you had to choose, which would you eat first?
  • I see you like traveling. I’m curious. If you were on a 12 hour international flight with a nice window seat, would you rather have a really upset stomach and have to go to the bathroom 10 times during the flight, or be stuck next to an Indian dude that smelled like curry?

Regardless of their response, you can follow up with another dumb question.

  • Then you work the personality questions into the humor. “You clearly don’t mind curry, what’s your favorite food?” or “You can’t stand curry, are you picky? what do you like to eat?”
  • Would you rather walk in on your grandma having sex, or have her walk in on you? (If they said they preferred grandma to walk in on them I would follow up) What if the guy is 350lbs and smells like an aged cheese? You’d still have a good time?

Questions to ask before a first date

Here are some great questions to ask before a first date or even a first date online. These questions are good date ice breaker questions too:

  1. What is your favorite place to eat out?
  2. My mom wants to come with us for our first date [wait a couple seconds] – just kidding!
  3. Do you like having picnics?
  4. Morning or evening dates?
  5. When do you have free time?
  6. I think you need me to help you with your studies!
  7. I hope I don’t make you miss too many classes!
  8. Why don’t we meet up at StarBucks at around 5pm?
  9. What do you think about going to a concert?
  10. What do you think about making pottery?
  11. I noticed you workout, how often do you go to the gym?
  12. I noticed you like traveling, where have you been?
  13. What is something about you that would surprise me?
  14. What is your favorite thing to do on a date?

For more ideas read: 50+ Hot Questions To Ask a Girlfriend

Good/ Great questions for a first date

The following questions are called “qualification questions” because you are making your girl qualify herself to you.

You say “I love mountain biking, what are you passionate about?” and she needs to prove herself to you by saying something that she’s passionate about i.e. working out, studying, etc.

It makes your girl wonder if you really like her or not. It’s a kind of flirting, it’s like you’re saying: “you’re OK, I’m not that impressed, prove to me that you’re worth my time.”

Here are some examples:

  1. I hope you are not the type of girl that spends all her money getting her nails done…
  2. I love mountain biking, what are you passionate about?
  3. I love working out, what do you do to look good?
  4. You look like the fun type of girl, although all of them say they are, what do you do that’s fun?
  5. Do you do anything in your life besides sitting around looking hot?
  6. So you are just looking to break someone else’s heart, am I right?
  7. So I guess your best friends would also call you boring…
  8. Do you ever know when to shut your mouth? You’re not always this way, right?
  9. Your acting like you didn’t get enough sleep last night
  10. I didn’t know you ate this type of junk food, I hope you are not the type of girl that doesn’t care about fitness
  11. You don’t have much respect for people, do you?

To learn more about qualification questions read: Why Do Girls Like Me? 8 Insightful Reasons

Funny questions for a first date

Here are my funniest questions that will make you fall in love from my post titled – What to Talk About on a Date: 27 Best Topics:

  1. Sooo…. When are we getting married?
  2. I need 12 kids by tomorrow morning, do you think we could get that done tonight? 😉
  3. I think you need a piggy back ride… right now!
  4. Now isn’t the best time to fall in love with me, what about later tonight?
  5. What is the funniest username you’ve ever seen online?
  6. What is something ridiculous your co-worker has ever done?
  7. Has your teacher ever farted while teaching?
  8. What is the funniest way to eat?
  9. Have you ever been scared of a cow?
  10. What is your funniest story?
  11. So when are you starting The International association for Tomato heads?
  12. What is the funniest compliment you’ve ever received?
  13. What is your funniest story with a creepy dude?
  14. What is the funniest thing you’ve seen at a friends house?
  15. What are some of the funniest things you daydream about?
  16. What was it like the first time you got drunk?
  17. How could you freak out any of your friends?
  18. If you had to be one character in your favorite comedy show, who would it be?
  19. How would you act if you were a guy?
  20. What do you think you’ll be like when you’re super old?
  21. If you would do anything crazy, what would it be?
  22. What do you do when no ones looking?
  23. What would be the first thing you did if you went back into your 7 year old body?
  24. If you had to live in a fairy tale, which one would it be?
  25. What is the funniest joke you’ve ever heard?
  26. What is the funniest prank you’ve ever seen?
  27. If you had a store, what would be the funniest thing you’d sell?
  28. What was the funniest thing you’ve done while being high?
  29. Who is your funniest relative? [1, 2]

Would you rather questions for a first date

Here are my best First date truth or dare questions from my article titled – What to do on a First Date: 23 Creative Ideas:

Truth: What was your worst kiss?

Dare: Sit in middle of the shopping mall for 1 full minute

Truth: Who was your 2nd grade crush?

Dare: Dance for 30 seconds in public

Truth: What was your most awkward moment with your parents?

Dare: Stare at any stranger for 10 seconds

asking a question on a first date

Questions for a first date to ask a guy

  1. What would be the first thing you did if you transformed into a girl?
  2. What makes you feel awesome?
  3. How much money do you plan on earning every year? How?
  4. Are looking for a hookup or a relationship?
  5. What do you think about kids?
  6. What is the hottest thing you’ve seen a woman wear?
  7. What do you do every day no matter what?
  8. Are you planning on becoming famous?
  9. If you ended up in jail, for what reason would you be there?
  10. What was your most awkward moment with your parents?
  11. What is your craziest friend like?
  12. How would you waste a million dollars?
  13. What is the #1 thing you regret doing?
  14. What are you proud of yourself?
  15. Entrepreneur or corporate?
  16. What was your biggest injury you’ve had in sports?
  17. Would you get yourself a pet? Which one would it be?

Questions to ask a girl on a first date

  1. What clothing do you wear when you’re feeling turned on?
  2. Where do you see yourself in a year?
  3. What did you do on your first job?
  4. What was your worst day at school like?
  5. Have you ever manipulated someone? What did you do?
  6. What type of family do you have?
  7. What did you do before your interview at your first job? How did you feel?
  8. Do you sing in the shower?
  9. What are you most proud of?
  10. Have you ever cried in front of everyone?
  11. What is something that you find funny, but people find crazy?

Best questions for a first date

  1. What would your dream house look like?
  2. What is your favorite style of dance?
  3. What is your dream vacation?
  4. What was your favorite TV show growing up?
  5. What was the craziest thing you’ve ever done on Halloween?
  6. What’s your favorite show on Netflix?
  7. What is your workout routine?
  8. Your hair looks amazing, what did you do this morning?
  9. What is your dream country?
  10. What was the worst prank you’ve fallen for?
  11. What was your favorite movie character as a kid?
  12. What was your worst experience while working?
  13. Have you ever cheated in school?
  14. Have you ever thought of writing your own book?
  15. What is something interesting about you that you’ve never told anyone else?
  16. What is your favorite sport?
  17. What was the warmest, most loving experience in your life?
  18. Who is your favorite celebrity?
  19. What was your worst moment in your life?
  20. Have you ever felt like an 80 year old?
  21. What has surprised you so far this year?
  22. Have you ever cheated on your boyfriend?
  23. Do you hook up with every guy you meet?
  24. Who was your crush in middle school? Why?
  25. What is the number one thing you must do within the next 10 years?
  26. What was the most beautiful secret you’ve ever seen?
  27. What is something that you can’t get enough of?
  28. Have you ever felt like a 5 year old while at work?
  29. Did you ever end up with a creep for a first date?
  30. How did you escape that creepy date?
  31. What would you be doing if you had 12 kids ages 1-5 years?!
  32. If you could tell the whole world one thing, what would it be?
  33. What is something that you wish you understood?
  34. What was the nastiest food you’ve ever tasted?
  35. What was the luckiest day of your life?
  36. If you could build anything, what would it be?
  37. If you could own anything for free, what would it be?
  38. What would be your perfect BBQ party?
  39. If you could watch 9/11 happen, would you want to?
  40. Do you like guys with big muscles or big brains?
  41. If you had 1 million dollars right now with 10 minutes to spend it, how would you spend it?
  42. If you could go into your past and chance something that you’ve done, what would it be?
  43. If you could start doing one habit what would it be?
  44. What celebrity would you want to meet in real life?
  45. What was the funniest line that a guy used to pick you up?
  46. What was the cutest line that a guy used to pick you up?
  47. What was the creepiest line that a guy used to pick you up?
  48. If you could get revenge on your boss, how would you?
  49. What is your favorite social media app?
  50. What is your biggest regret?
  51. What is your favorite alcoholic beverage?
  52. Are you scared of spiders
  53. Would you ever put pineapple on your pizza
  54. What was the worst way you’ve ever spent your money one?
  55. Have you ever been hit on by another girl?
  56. What is your sexiest dress?
  57. What do you think about going to a museum?
  58. What song makes you cry?
  59. Do you like smart guys?
  60. What is your favorite quote of all time?
  61. What do your parents think of you?
  62. Have you ever tried role play?
  63. What do you do that makes you feel sad?
  64. Would you ever work on a farm?
  65. Would you ever work at a strip club?
  66. What are you planning on studying at university?
  67. What do you hate about your younger brother?
  68. What was the craziest fight you’ve had with your siblings?
  69. How do you waste your time
  70. What was the craziest account you’ve had with a stranger?
  71. What is your craziest opinion?
  72. Do you like older guys?
  73. Do you think there are real ghosts?
  74. What has been your craziest dream?
  75. What do you think when you look at yourself in the mirror?
  76. What has been the naughtiest thing you’ve ever done?
  77. Who was your first best friend?
  78. Did you ever have love at first site?
  79. What was your most awkward kiss?
  80. Have you ever been in the friend zone?
  81. Are you the type of girl that gets super drunk?
  82. Have you ever been seen as a hero?
  83. What is something you want to learn?
  84. What is something you can’t get yourself to do?
  85. Have you ever been embarrassed to cry?
  86. What was your angriest moment?
  87. How do you plan to survive a zombie attack?
  88. Would you live in the 1700’s if you could?
  89. Have you ever manipulated anyone?
  90. What was the best gift you’ve ever visited?
  91. As a child what did you want to become?
  92. What did you do as a child that drove your parents mad?
  93. What was the worst advice you’ve ever listened to?
  94. When are we going to have the most romantic make out session?
  95. What is something you just don’t understand about guys?
  96. Did you ever think that you were gay or bisexual?
  97. What is something about me that drives you nuts?
  98. How is your hair so naturally shiny?
  99. I love your sense of style, where did you buy it?
  100. Where did you learn how to be so likable?

asking a question on a first date

Questions you should never ask on a first date:

  1. Are you on your period?
  2. How much do you weigh?
  3. Do you even earn money?
  4. What is that bulge between your legs?
  5. Why won’t you pay for my food?
  6. Why won’t you grow up?  [3, 4]


Before you start using all these great questions, I want you to remember that you don’t have to do all the talking.

Don’t force yourself to keep the conversation moving. Don’t feel pressured and anyways, the less you care, the better the date.

Your friend,

Colt Smith

{"email":"Email address invalid","url":"Website address invalid","required":"Required field missing"}

About the author 

Coach Colt here, the founder of Dating Armory, your go-to source for no-nonsense, practical relationship advice. I'm a bisexual male in a same-sex open relationship and a researcher in sex, love, and relationships with 7+ years of experience. I specialize in helping both men and women navigate the crazy world of dating.

Don't miss my other guides packed with practical dating advice (no bullshit repeated Platitudes) and tons of real life examples:

My Top 57 First Date Ideas That Always Work (As a Dating Coach)

Are Coffee Dates Good? It (Kinda) Depends

17 Basic Coffee Date Tips (From a Dating Coach)

How to Get a Gay Boyfriend: 25 Tips That Work