On a city rooftop under thick clouds, a woman in a purple hat, wrapped in a plaid blanket, points up hopefully at the starless sky while the man beside her clutches a thermos and gives her a flat look, and a pizza box blows past.

300 First date questions

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Here is our list of first date questions, sorted from easy openers to fun, deep, a little weird and flirty, plus some to text before you meet. Perfect for finding things that you have in common with your date.

Easy first date questions

  1. What do you like to do in your free time?
  2. Are you more of an indoors or outdoors person?
  3. Who is the most fascinating person you’ve met?
  4. What was the last book you really got into?
  5. What are some movies you really enjoyed?
  6. What amazing adventures have you been on?
  7. What pets have you had?
  8. What’s your favorite alcoholic and non-alcoholic drink?
  9. What are you kind of obsessed with these days?
  10. Where have you traveled?
  11. What food from another country could you happily eat every week?
  12. Are you a morning person or a night owl?
  13. What’s your favorite restaurant?
  14. How many siblings do you have?
  15. What would be your dream job?
  16. What would you do if you had enough money to not need a job?
  17. Who is your favorite author?
  18. What was the last show you binge-watched?
  19. What TV series do you keep coming back to and re-watching?
  20. What hobbies would you like to get into if you had the time and money?
  21. What would your perfect vacation look like?
  22. What music artist do you never get tired of?
  23. What’s the best thing that has happened to you this month?
  24. What would your perfect morning be like?
  25. Is there any art or artist you are really into?
  26. What do you do to unwind?
  27. What would be the best city to live in?
  28. What would you like to know more about, but haven’t had the time to look into it?
  29. Do you prefer to work in a team or alone?
  30. How techie are you?
  31. Where is the most fun place around where you live?
  32. Have you ever joined any meetup groups?
  33. What’s the most relaxing situation you could imagine?
  34. What is the most beautiful view you’ve seen?
  35. What’s the most recent thing you’ve done for the first time?
  36. How did you come to love one of your favorite musicians?
  37. How did you meet your best friend?
  38. Where would you move if you could move anywhere in the world and still find a job and maintain a reasonable standard of living?
  39. What did you do last summer?
  40. What did you do for the last holiday, and what are you doing for the next one?
  41. Who’s your favorite actor or actress?
  42. Who’s your favorite character from a TV show, movie, or book?
  43. What TV shows did you watch when you were a kid?
  44. What’s your favorite smell?
  45. What skill or ability have you always wanted to learn?
  46. What’s the best meal you’ve ever had?
  47. Where was your favorite place to go when you were a kid?
  48. What places have you visited that exceeded your expectations?
  49. What road trip story do you still tell?
  50. Besides your home and your work, where do you spend most of your time?
  51. What are your top 3 favorite things to talk about?
  52. Where would you like to retire?
  53. What are people often surprised to learn about you?
  54. What’s your go-to series or movie when you want to watch something but can’t find anything to watch?
  55. How many other countries have you visited?
  56. What holiday do you go all out for?
  57. Where's the best place around here to have a picnic?
  58. What’s your favorite thing to do outdoors? How about indoors?
  59. What do you never get tired of?
  60. What’s the last new thing you tried?
  61. On a weekend or holiday, what’s the best time of day and the best time of night?
  62. What are you looking forward to that’s happening soon?
  63. Where did you take family vacations to when you were younger?
  64. What’s something you’re interested in that most people wouldn’t expect?

Fun first date questions

  1. If there was an Olympics for everyday activities, what activity would you have a good chance at winning a medal in?
  2. What are you still using that everyone says you should replace?
  3. Among your friends, what are you best known for?
  4. What happens when you're put in charge of directions?
  5. What are some obscure things that you are or were really into?
  6. What do you order that makes the bartender judge you a little?
  7. What are some things everyone should try at least once?
  8. What game is banned in your family, and what happened?
  9. What fad did you never really understand?
  10. If your hometown had a local legend about you, what would it be?
  11. What are you always game for?
  12. Who's the most famous person you've met, and how did you play it cool?
  13. Cutest animal? Ugliest animal?
  14. What skill from an old job refuses to leave you?
  15. Where’s the strangest place you’ve ever been?
  16. What little mixup became a running joke?
  17. What harmless thing scares you way more than it should?
  18. What do you get competitive about that absolutely doesn't matter?
  19. What household chore is just the worst?
  20. What perfectly normal food took you years to trust?
  21. If you could give yourself a nickname, what nickname would you want people to call you?
  22. What teenage fashion choice do you have to explain in old photos?
  23. What odd talent do you have?
  24. What phase did you go through that your friends still bring up?
  25. What country do you never want to visit?
  26. Which childhood gift would still get you pretty excited?
  27. Where would your friends or family be most surprised to find you?
  28. What food combination do you keep trying to talk people into?
  29. What’s expensive but totally worth it?
  30. What do you get roasted for in your friend group?
  31. If you had to be famous, what would you want to be famous for?
  32. What do you always end up bringing to a party?
  33. Before you make a call, do you rehearse what you are going to say?
  34. What's the funniest group chat you're in, and what's it called?
  35. When was the last time you sang to yourself or to someone else?
  36. What place did you stop going to for a really petty reason?
  37. When was the last time you walked for more than an hour?
  38. What does your family do that requires explaining to guests?
  39. Best and worst flavor ice cream? What would make for an excellent new ice cream flavor?
  40. What do you keep getting volunteered for?
  41. All modesty aside, what are you better at than 90% of people? It doesn’t have to be useful or serious, it can be something ridiculous.
  42. What's the best thing you've ever found on the ground?
  43. What’s the most interesting fact you know?
  44. What did your bedroom walls look like when you were 14?
  45. What store makes you forget what you came for?
  46. What do you like but are kind of embarrassed to admit?
  47. What did you learn about someone by helping them move?
  48. What's the biggest crowd you've had to present something in front of?
  49. How do you start or join a conversation at a party full of strangers?
  50. What’s something that most people haven’t done, but you have?
  51. What ridiculous thing has a town you've lived in bragged about?
  52. What machine or appliance in your house aggravates you the most?
  53. What have you ordered by pointing and hoping?
  54. What business would you be terrible at running?
  55. What trivial argument are you prepared to drag out forever?
  56. What’s the worst movie you’ve ever seen?
  57. What's the best costume you've ever pulled off?
  58. What do you care least about?
  59. What dish makes people overestimate your cooking skills?
  60. Would you rather live full time in an RV or full time on a sailboat?
  61. What purchase do you still defend even though you get grief for it?
  62. What’s the strangest way you’ve become friends with someone?
  63. What do you have to stop yourself from correcting?
  64. What companies made you so mad that you would rather suffer bodily harm than give them any more of your money?
  65. What did you get way too excited about recently?
  66. What’s the most ridiculous thing you’ve done because you were bored?
  67. What did you discover you were saying wrong?
  68. How often do you dance? Silly/ironic dancing counts.
  69. How much fun have you managed on twenty bucks?
  70. What’s the most spontaneous thing you’ve done?
  71. What's on your fridge door right now?
  72. What really cheesy song do you love?
  73. What has a kid or a pet done around you lately that made you laugh?
  74. What’s the worst or best job you’ve had?
  75. What’s your go-to funny story?
  76. If the company you work for / the college you go to had an honest slogan, what would it be?
  77. How well do you cope when you don’t have your phone with you for an extended period of time?
  78. Would you rather have an incredibly fast car or incredibly fast internet speed?
  79. What are the top three social situations you try to avoid most?
  80. What took you way too long to figure out?
  81. What nicknames have you had throughout your life?
  82. Where’s the last place you’d ever go?
  83. What fact floored you when you heard it?
  84. If you unexpectedly won $10,000, what would you spend it on?

Deep first date questions

  1. What are some accomplishments that you are really proud of?
  2. What did you assume grown ups had figured out until you became one?
  3. Who is the kindest person you know?
  4. What's something you were raised to believe that you had to unlearn?
  5. Who are your kind of people?
  6. What small promise do you take pretty seriously?
  7. If you could give everyone just one piece of advice, what would it be?
  8. What did someone talk you out of being wrong about?
  9. What wrong assumptions do people make about you?
  10. What's a skill one of your parents had that you wish you'd picked up?
  11. What has been the best period of your life so far?
  12. What's something you changed your mind about in the last few years?
  13. How have you changed from when you were in high school?
  14. What would twelve-year-old you think of your life right now?
  15. When do you feel most out of place?
  16. What are you stubborn about, and why is that a good thing?
  17. What small seemingly insignificant decision had a massive impact on your life?
  18. What do you hope you never get too sensible for?
  19. If you lived to 100, would you rather keep the body or the mind of yourself at 30 until you were 100?
  20. What good advice do you keep finding reasons to ignore?
  21. What are you most grateful for?
  22. What kindness from a stranger came at just the right time?
  23. What’s the most essential part of a friendship?
  24. What's something you're bad at and have made your peace with?
  25. If you knew you were going to die in a year, what would you change about how you live?
  26. What are you learning that's making you feel like a beginner again?
  27. How much personal space do you need to be comfortable?
  28. What kind of old person are you already becoming?
  29. What says the most about a person?
  30. What do people apologize for that doesn't bother you?
  31. What’s the worst advice someone has given you?
  32. When has someone trusted you before you trusted yourself?
  33. If you could have the answer to any one question, what question would you want the answer to?
  34. What compliment meant more to you than the person probably realized?
  35. When you were a kid, what seemed like the best thing about being a grown up?
  36. What do you think people should be more embarrassed about than they are?
  37. What were some of the turning points in your life?
  38. What did your family argue about at the dinner table?
  39. What small things brighten up your day when they happen?
  40. What are you glad you did but are never doing again?
  41. If you could send one letter to yourself in the past without the goal of making yourself rich (no lotto numbers, stock picks, etc.), what age would you choose and what would the letter say?
  42. What have you come to appreciate about someone you disagree with?
  43. What do you miss about life 10 or 20 years ago?
  44. What risk failed but still feels worth taking?
  45. What’s getting worse and worse as you get older? What’s getting better and better as you get older?
  46. What's a rule you live by that you made up yourself?
  47. What habit do you wish you could start?
  48. What deserves a celebration even if there's no card for it?
  49. What’s the best way to get to know who someone really is?
  50. What's a fight you're glad you lost?
  51. Who besides your parents taught you the most about life?
  52. What do people get wrong about your job?
  53. When are you the most “you” that you can be? In other words, when do you feel most like yourself?
  54. What did you do against everyone's advice that worked out?
  55. How much social interaction is too much?
  56. When do you hear your parents coming out of your mouth?
  57. How different do you act when you are with acquaintances vs. people you are comfortable with?
  58. What were you rebellious about as a kid, and did any of it stick?
  59. What’s been the most significant plot twist in your own life?
  60. When has changing your mind felt like a relief?
  61. What were some of the happiest times of your life so far?
  62. Where do you feel at home before you've unpacked?
  63. Which friendship has had the biggest impact on you?
  64. When did you first feel like an actual adult?
  65. What’s your favorite quote or saying?
  66. What's something you'll always make time for, no matter how busy you get?
  67. If you had the power to change one law, what law would you change?
  68. What do you believe that most of your friends don't?
  69. What’s the hardest you’ve worked for something?
  70. What part of your life now will you probably miss in the future?
  71. What do you do differently than most people?
  72. What kind of effort do you notice that often goes unnoticed?
  73. Who is the best role model a person could have?
  74. Which movie found you at exactly the right time?
  75. What do you think your parents got right?
  76. What's a small kindness someone did for you that they've probably forgotten?
  77. What has a job taught you about how to treat people?

Weird first date questions

  1. What’s your favorite piece of furniture you’ve ever owned?
  2. What would be hard to explain about your day to a medieval peasant?
  3. What’s the strangest phone conversation you’ve ever had?
  4. What would people do on a holiday you invented?
  5. If you could go back in time as an observer, no one could see you, and you couldn’t interact with anything, when would you want to go back to?
  6. What perfectly normal place feels like you're not supposed to be there?
  7. If you found a briefcase with $1 million in $100 bills on your doorstep, what would you do with it?
  8. What animal gets way more respect than it deserves?
  9. Who is the most bizarre person you’ve met?
  10. What job do you think you could fake your way through for a week?
  11. What would you do with the extra time if you never had to sleep?
  12. What's in your search history that would need some explaining?
  13. What sports would be funniest if the athletes had to be drunk while playing?
  14. Which store could keep you entertained if you got locked in overnight?
  15. What's your favorite band name (not necessarily your favorite band)?
  16. What useless fact lives rent free in your head?
  17. What’s happening now, that in 20 years people will look back on and laugh about?
  18. What have you seen for sale that raised more questions than answers?
  19. If you could instantly receive a Ph.D. in any discipline including all the knowledge and experience that goes along with it, what would your Ph.D. be in?
  20. What looks like it should make a noise but doesn't?
  21. What do you suspect everyone else is just pretending to understand?
  22. What would the warning label on you say?
  23. What's the strangest thing you own, and why do you still have it?
  24. What do you imagine happens in stores after everyone leaves?
  25. What's a normal thing you find deeply suspicious?
  26. What harmless conspiracy could you start about your local grocery store?
  27. What boring job looks secretly pretty fun to you?
  28. What crime would you be terrible at committing?
  29. What's something you only trust when it looks a little beaten up?
  30. What deserves a warning label even though it's harmless?
  31. What lie would you sneak onto your own Wikipedia page?
  32. If you got arrested tonight, what would everyone assume you did?
  33. What word should exist but doesn't?
  34. If you came back as a ghost, where would you haunt and who would you mess with?
  35. You're a dragon who's bored with gold. What are you hoarding?
  36. What would a roommate give you one star for?
  37. Which historical figure would be the worst roommate?
  38. What house rule did you grow up with that you later found out was weird?
  39. Realistically, what are your last words going to be?
  40. If you were a pro wrestler, what's your entrance song and finishing move?
  41. What conspiracy theory do you secretly want to be true?
  42. What's the biggest animal you think you could take in a fight?
  43. Which legendary creature would you be pleased to hear actually exists?
  44. If you went into witness protection, what fake life would you pick?
  45. What sounds fake even when you're the one explaining it?
  46. What tiny mystery in your neighborhood needs solving?
  47. What have you found that left you with a lot of questions?
  48. What completely wrong explanation made sense to you as a kid?

Flirty first date questions

  1. How soon after a good date should the first text come?
  2. What's the most effort you've put into a text that was supposed to look casual?
  3. What were you nervous about before meeting me?
  4. What's the boldest thing you've done to get someone's number?
  5. What kind of trouble could you talk me into?
  6. What hobby have you faked an interest in for someone you liked?
  7. What's your flirting style, honestly?
  8. What's the most romantic thing you've seen a stranger do?
  9. What would your exes agree is your best quality?
  10. What's the worst way someone has asked you out?
  11. Who taught you how to flirt, and how's that working out?
  12. What sounds attractive on paper but never works on you?
  13. What makes someone get better looking as they talk?
  14. What song would get you to ask someone to dance?
  15. What opening line worked on you despite your better judgment?
  16. What date idea sounds romantic but is miserable in real life?
  17. What's your best pickup line, and how often has it actually worked?
  18. What did you get completely wrong about dating when you were younger?
  19. What outfit lost to the one you wore today?
  20. How do you get through a slow dance when you can't dance?
  21. How would your friends review your flirting?
  22. Who in your family would grill a date the hardest?
  23. What kind of nerdy do you find attractive?
  24. How did you try to impress a crush as a teen?
  25. What's the smoothest thing anyone has ever said to you?
  26. What have you guessed about me so far?
  27. What was your escape plan if we didn't hit it off?
  28. How would you improve the traditional dinner date?
  29. What would your friends say your type is? Do you agree?
  30. What could someone be hilariously bad at and still charm you?
  31. What are you hoping I don't ask you tonight?
  32. What's your most charming bad habit?
  33. What's a ridiculous excuse you've used to talk to someone cute?
  34. What gives you away when you're trying to play it cool?
  35. What would make getting caught in the rain a good date?
  36. What's something about you that gets more attractive the longer someone knows you?
  37. Where would you take me to see you in your element?
  38. What would we be arguing about in a cooking class?
  39. What ordinary skill do you find unreasonably attractive?
  40. What makes being nervous around someone part of the fun?
  41. What romantic movie nonsense would actually work on you?
  42. What kind of goodbye makes you smile on the way home?
  43. What could I tease you about and still get another date?

Questions to text before a first date

  1. Which of your profile photos needs an explanation?
  2. What did you overhear this week that you can't stop thinking about?
  3. What's the best thing you've eaten this week?
  4. What does a Sunday look like when nobody needs anything from you?
  5. What emoji do you use way too much?
  6. What did you buy recently that you're a little too excited about?
  7. What's your drink order, so I can plan ahead?
  8. What place near you is overrated, and where should we go instead?
  9. What do you insist on picking out in person?
  10. Out of ten, how's your week going, and what's the headline?
  11. What's your bad haircut story in two sentences?
  12. What small thing ruins your mood instantly?
  13. What song have you had on repeat this week?
  14. What's your honest answer when someone asks what you do for fun?
  15. What movie title sums up your day so far?
  16. What song are you playing first if you get the aux?
  17. What went off the rails at work this week?
  18. What video did someone send you this week that you've watched more than once?
  19. What did you do today that deserves a little applause?
  20. What would you order for us if I left you in charge?
  21. What was your first concert, and how does it hold up?
  22. What word does your phone keep autocorrecting wrong?
  23. What did you recently have to talk yourself out of buying?
  24. What opinion can you defend in ten words?
  25. What did you pass today that was worth stopping for?
  26. What's your policy on stealing a fry from my plate?
  27. What are you procrastinating on right now?
  28. What meme sums up your week?
  29. What's the best gas station snack?
  30. What's the last thing that made you laugh out loud?
  31. What's a food you'd never order on a date?
  32. What situation always gets the same GIF from you?
  33. What should I know before I meet you in person?
  34. What would your friends add to your dating profile?
  35. What did you plan for tonight before the couch got involved?

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