355 Funny First Date Questions for a Successful Date Conversation

Going on first date and dont know what to ask or say to him or her. We know this feeling because we all have been through this. But now no more this waiting to think and ask game anymore. Read below and check out our funny first date questions for a successful date conversation article to crack the date.

We’ve all been on a boring first date that feels like an interview, or even worse, a date where neither person can think of any questions to ask the other.

So here are some tips to help you. We’ll give you some of our favorite funny first-date questions that are sure to get the conversation going and help you both have a great time. So get ready to laugh, and let’s get started.

Funny First Date Questions

  1. Is your first thought about me good or bad?
  2. Should toilet paper hang above or below the toilet?
  3. What is your go-to song for karaoke?
  4. If you could be a popular person for a day, who would it be?
  5. What’s your favorite joke of all time?
  6. Do you always sing along when you hear a certain song?
  7. What’s the movie you’re most ashamed to say you like?
  8. What was the dumbest thing you did to try to make someone like you?
  9. What was the strangest thing you did as a kid that makes you feel bad now?
  10. Which character from “The Office” would you be, and why?
  11. From what movie can you say every line?
  12. Who did you first have a crush on?
  13. What’s the weirdest dress trend you’ve ever followed?
  14. Who would you like to have as a relative?
  15. Can you think of the worst dress trend you tried in middle school? What’s that? 
  16. What did you often get in trouble for when you were younger?
  17. Has anyone ever told you that you look like a well-known person?
  18. Do you worry about anything that might make you look bad? Do you have a fear of something that most people wouldn’t find scary
  19. How many selfies do you have to take before you get the right one? (Or is it a problem?)
  20. Did someone ever call you by the wrong name and you didn’t want to tell them? What did they call you if so
  21. Could someone figure out who you are from your Spotify or Netflix account alone?
  22. Who do you find beautiful that most other people don’t?
  23. What’s the craziest thing you’ve done to try and impress someone?
  24. What would you be topped with if you were a pizza?
  25. What was the worst or oddest first date you ever went on?
  26. Can you make someone else’s speech sound like yours? If so, I’d like to know!
  27. What’s the craziest thing you ever did on a dare?
  28. What would your unique move be if you were a video game character?
  29. How could you leave without being rude if you felt like you had to?
  30. If your life were a “expectation vs. reality” joke, what two pictures would you pick?
  31. Who was your most awkward crush? Or old love? (Be truthful!)
  32. How long do you spend every day on TikTok?
  33. What’s the best name you’ve ever seen for a WiFi network?
  34. What odd mix of tastes do you really like?
  35. Who would you choose as your new best friend if you could pick a famous person?
  36. What would they call the movie about your life?
  37. What was one of those things you thought for a long time when you were young?
  38. What cartoon character do you think you are most like?
  39. What about the other sex bugs you the most?
  40. What would you want if you could have three dreams come true?
  41. What do you think you know but are probably wrong about?
  42. What would be on the label if you had one?
  43. When you really shouldn’t have, when did you find yourself laughing when you shouldn’t have? 
  44. What are the best parts of a pizza?
  45. What’s the best and worst outfit you’ve ever worn for Halloween? 
  46. Should there be pineapple on pizza?
  47. What song would you sing if you had to sing at a karaoke bar?
  48. What would your rapper’s name be?
  49. What would you like to break the law the most?
  50. What would you call yourself if you were a DJ for the night?
  51. If you didn’t have to work, what would you do with your time?
  52. Which praise about you stands out as the best?
  53. Do you have any pets? What are you going to tell them?
  54. Which is a better way to start an awkward conversation: talking about the weather or food?
  55. When did you last do something nice for yourself?
  56. How would you sum up social media in one sentence?
  57. What’s the worst outfit you’ve ever had to wear?
  58. Have you ever been the target of a joke that wasn’t what it seemed? Have you ever been able to pull one off?
  59. Which animal makes the funniest sounds?
  60. What would you do first if you were a crab?
  61. Who would you want to be from a game or movie you played or watched as a kid?
  62. What did you love that was a bad waste of your money?
  63. What’s the weirdest or most embarrassing thing you’re scared of?
  64. What have you done that you think everyone else should do too?
  65. What was the worst shot you took in school?
  66. Is there a song whose words you’ve been singing wrong for a long time?
  67. Do you have a word that you have always said wrong?
  68. How would you say what you want to say if you could only use emojis for a day?
  69. What would you do first if you could instantly change your gender?
  70. If you could only eat one meal for the rest of your life, what would you choose?
  71. What book would you choose if you were stuck on a deserted island and could only bring one?
  72. What’s the strangest thing you’ve ever gotten or given as a gift?
  73. What’s the one ability you’d most like to have?

Funny First Date Questions To Ask A Girl

Funny First Date Questions To Ask A Girl

If you are a boy and looking for a list of engaging and funny first date questions to ask a girl. Why fear we are here read this complete list of 38 questions. We bet after asking this questions you will definitely impress your girl.

  1. Have you ever accidentally sent a text or email to someone about whom you were complaining?
  2. What’s the strangest thing you’ve ever put in your mouth?
  3. Have you ever loved a celebrity so much that you cried when they started dating someone else?
  4. If you could have any pet, no matter how useful it would be, what would it be?
  5. What’s the skill you’re least likely to use?
  6. What’s the most hidden skill you have that no one knows about?
  7. Would you rather fight a duck the size of a horse or a horse the size of a duck?
  8. What kind of treat would you be if you were one, and why?
  9. If you couldn’t talk and could only make the sound of an animal, which animal would you pick?
  10. How come Mickey went to space?
  11. What would you choose if you could have any ability, but it had to be completely useless?
  12. If you could go back in time to any point in history, when and why would you go there?
  13. If you could be any character from a book or movie, who would it be and why?
  14. What’s the weirdest thing you’ve ever dreamed?
  15. If you could live anywhere in the world, where would you go and why?
  16. What is the most embarrassing thing that has ever happened to you in public?
  17. Would you rather have troll doll hair or no eyebrows?
  18. If you could spend a day in the life of any famous person, who would it be and why?
  19. Do you think you could stay alive if zombies took over the world?
  20. What’s the worst way someone has tried to get your attention?
  21. What’s the craziest thing you’ve ever worn to a costume party?
  22. Who would you be and why if you could be any Disney villain?
  23. What food would you choose to look like for the rest of your life if you had to?
  24. How many selfies do you have to take before you find the right one?
  25. If you could spend a day in someone else’s shoes, who would it be and why?
  26. Do you do anything weird or have any strange habits?
  27. What was the funniest joke you ever played on someone?
  28. What’s the craziest dress trend you’ve ever followed?
  29. If Cinderella’s shoe fit well, why did it fall off?
  30. What song on your playlist makes you feel the most ashamed?
  31. Which celebrity pair do you think has the best relationship?
  32. What’s the funniest pickup line you’ve ever heard?
  33. Are you as cool as you seem on Facebook in real life?
  34. What is your guilty pleasure TV show?
  35. What was your ex’s most annoying habit? 
  36. How do you feel about pineapple on pizza?
  37. Is there a show, movie, or book you like that makes you feel bad about yourself?
  38. Which would you rather have: to always look like a fish or to always smell like a fish?

Funny First Date Questions To Ask A Guy

Funny First Date Questions To Ask A Guy
  1. When did you last urinate in a pool?
  2. If you could have any pet, no matter how useful it would be, what would it be?
  3. What’s the worst thing you’ve ever looked up on Google?
  4. What’s the strangest thing you’ve ever put in your mouth?
  5. What’s the weirdest thing you’ve ever dreamed?
  6. If you could spend a day in the life of any famous person, who would it be and why?
  7. What was the funniest joke you ever played on someone?
  8. Do you think aliens exist? If that’s the case, how do you think they look?
  9. If you had to be an inanimate item for a year, what would you choose to be?
  10. Do you think I look like the picture I use on social media?
  11. Have you ever texted someone while you were drunk that you wish you hadn’t?
  12. What game did you play really well?
  13. What song do you listen to when you’re about to get into a fight?
  14. Who from a cartoon do you think you are most like?
  15. What would you do for a living if you lived through the end of the world?
  16. What would you call yourself if you were a DJ?
  17. Imagine that you went to jail because you did something bad. How would you have handled it?
  18. What about the ad made you decide not to buy the product?
  19. Have you ever been driving home and couldn’t stop to use the bathroom?
  20. Who would do the best job if a movie were made about your life?
  21. What kind of food would you be, and why?
  22. Which character on a TV show would you want to be and why?
  23. What would you choose if you could have any ability, but it had to be completely useless?
  24. If you could live anywhere in the world, where would you go and why?
  25. If you could be any character from a book or movie, who would it be and why?
  26. What would be the one rule that everyone must follow for a day?
  27. What’s the most unusual skill you have?
  28. If you could spend a day in someone else’s shoes, who would it be and why?
  29. What’s your best joke about a dad?
  30. What’s your favorite food for a hangover?
  31. Where is the most unusual place you’ve ever gone to the bathroom?
  32. Do you have any fears or habits that make you stand out?
  33. Who would you marry if you could marry any character from a story?
  34. What’s the worst way someone has tried to get your attention?
  35. Do your best guess about me based on what you already know about me.
  36. What song on your playlist makes you feel the most ashamed?
  37. What would you eat for the rest of your life if you could only eat one thing?
  38. Would you rather fight a duck the size of a horse or a horse the size of a duck?
  39. What book would you choose if you were stuck on a desert island and could only bring one?

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Flirty first date questions

  1. What ability would you want to have in the bedroom?
  2. What’s the hottest thing you own to wear?
  3. You do know that you’re great, right?
  4. What makes you smile so beautifully?
  5. Do you always have this much fun?
  6. Do you think you could meet someone you like today?
  7. Where did you hook up that was the most unusual?
  8. Do you like to make the first move or have someone come up to you?
  9. What three words would you use to describe your perfect kiss?
  10. Where do you like to be kissed the most?
  11. How much more in love with you do you want me to get?
  12. Have you ever dreamed about someone you know in a bad way? Who were they?
  13. What turns you on the most, and why?
  14. What is the hottest thing you’ve ever done?
  15. Can I still look at you?
  16. Want to go to a quiet place?
  17. Do you think that love can happen at first sight?
  18. If you could choose one famous person to be your “Hall Pass,” who would it be?
  19. What do you like most about hugs?
  20. Do you want to go on a trip with me?
  21. What gets you going?
  22. What are you like?
  23. Did I just see you taking a look at me?
  24. Do you still want to hang out with me?
  25. Have you ever sent a dirty text to the wrong person? What went wrong?
  26. You know that you’re the most beautiful person in the room, right?
  27. What’s the dirtiest thing you’ve ever done on a date?
  28. Are you ready to meet someone special?
  29. Are you a lover who can’t give up?
  30. Which would you rather do: go skinny-dipping or make out in the rain?
  31. Do you know that you sometimes make me crazy?
  32. Is it too early to tell you how great it is to be with you?
  33. How can I get to know you better?
  34. How long will it be before you realize I’m looking at you?
  35. What great science that your atoms are the same as mine!
  36. Do you want to try something new tonight?
  37. You don’t seem to know how great you are, do you?
  38. Where do you think we should go next?
  39. What do you think makes the best date night?
  40. If you could only praise one part of my body, what would it be?
  41. Do you know what you want to do with the rest of your life? Or do you want me to help?
  42. Do you get the same butterflies I do?
  43. Who do you think would win if we played strip poker right now?
  44. How can I get eyes that look like yours?
  45. Want to find out a secret?
  46. What’s the most exciting thing you’ve ever done while you were in bed?
  47. What’s on your mind right now?
  48. You make me feel good. Can I do the same for you?
  49. Have you ever gone skinny-dipping? If you haven’t, do you want to?
  50. What is the thing you like most about a partner?
  51. What would you want to do if we were alone right now?

Deep First Date Questions

  1. If you could only give to or work for one charity for the rest of your life, which would you choose?
  2. What does your best friend think is the worst thing about you?
  3. What would you want to do in your last 48 hours if you only had that long to live?
  4. What would you do if all of a sudden you turned into a man or woman?
  5. Do you like getting up early or staying up late?
  6. When do you feel like you don’t belong?
  7. How do you think your next relationship will end (marriage, one-night stand, etc.)?
  8. What’s the worst date you ever went on?
  9. What was the most stupid thing you did as a kid?
  10. What is your most embarrassing fear?
  11. What are you crazy about right now?
  12. What are some bad things you have gotten hooked on?
  13. Do you know more than one language?
  14. What’s your biggest fear that makes no sense?
  15. Tell me two facts and a lie, and I’ll try to figure out which one is the lie.
  16. What would be the one thing you would tell your younger self?
  17. What would you change about your life if you knew you were going to die in 6 months?
  18. How would your mom describe you in three words?
  19. When do you want to be alone the most?
  20. When I say the word “love,” what’s the first thing you think of?
  21. What was the worst first date you’ve ever been on?
  22. Where did you go that was the most unusual?
  23. What is the smallest choice you’ve made that has changed your life the most?
  24. How often do you do one of the seven fatal sins?
  25. What do you usually do when you get into a fight?
  26. Which is more important to you: being close emotionally or being close physically?
  27. When did you last sing a song for someone else?
  28. Why do you think you still don’t have a date?
  29. What’s the most embarrassing thing that’s ever happened to you?
  30. What has been your favorite year so far?
  31. Which side of your brain do you use more?
  32. What role does religion play in your life?
  33. What is the strangest thing someone has ever said to you?
  34. What’s the best thing about a partner for you?
  35. When did you last go out on a date?
  36. What hobbies would you do if you had the time and money to do them?
  37. How would your mom describe you in three words?
  38. Do you know what language of love you speak?
  39. Would your boss pick you to take his or her place?
  40. Do you think everyone is meant to be with that “one” person or soul mate?
  41. Do you think that everyone is meant to be with that “one” person?
  42. What’s the worst date you’ve had outside? 
  43. Tell me about the most crazy thing on your list.

Funny Questions To Make You Think and Push your Conversation Ahead

  1. Which would you rather have: the ability to fly or the ability to teleport?
  2. Why do square boxes come with round pizzas?
  3. Which would you rather have: to be the smartest person in the world but also the person everyone dislikes the most, or to be averagely smart but liked by everyone you meet?
  4. Do you think a naan thrown like a Frisbee or a loaf thrown like a javelin would go farther?
  5. Why does ketchup not go well with potatoes but goes well with French fries?
  6. Do you think a naan thrown like a Frisbee or a loaf thrown like a javelin would go farther?
  7. Would you rather always have itchy skin or always have sticky skin?
  8. What kind of slightly annoying curse do you want to hurl at people?
  9. What would your friends and family think you did if you were caught and no one told them why?
  10. If you could have dinner with any intellectual, living or dead, who would it be and why?
  11. Which world would you rather live in: one without art or one without science?
  12. What would you want to know if you could find out the answer to any question?
  13. When you choke the Smurf, what color will it turn?
  14. Would you rather have a bad short-term memory or a bad long-term memory?
  15. Which time period would you choose to live in and why?
  16. What would your friends and family think you did if you were caught and no one told them why?
  17. Would you rather have a bad short-term memory or a bad long-term memory?
  18. What would you eat for the rest of your life if you could only eat one thing?
  19. What sport would be the most funny if everyone had to drink a certain amount?
  20. Who would you rather fight, a Ninja or a Navy Seal? 
  21. If you could decide to live forever, would you? What’s the deal?
  22. Which would you rather have on a deserted island: a copy of your favorite book or enough of your favorite food to last a lifetime?
  23. Which would you rather have: a perfect memory or the power to forget whatever you want?
  24. What kind of dog would you want to be if you were one?
  25. kid oil doesn’t come from a kid, like coconut oil does.
  26. If a turtle doesn’t have a shell, is he naked or homeless?
  27. Which would you rather have: the ability to go back in time to any point in history or to see into the future?
  28. Which place from a book or movie would you most like to visit?
  29. What would you prefer to do: Say all your words backwards or talk for a week only through charades?
  30. Why doesn’t the glue stick to the inside of the jar it comes in?
  31. Why do you press harder on the buttons on your remote control when you know the batteries are dead?
  32. Does the Energizer Bunny have power if it strikes someone?
  33. Who would you choose to be a fantasy character for a day and why?
  34. If you could live in any country other than your own, which one would you choose and why?
  35. Why aren’t rocks a better name for hemorrhoids? 
  36. Do you have any idea what your dog thinks of you?
  37. Which would you rather have: the ability to speak and understand every language in the world, or the ability to talk to animals?
  38. Which would you rather have: a perfect memory but bad physical coordination, or perfect coordination but a terrible memory?
  39. Do eyebrows count as hair on the face?
  40. Which would you rather do for a living: write famous books or play famous music?
  41. If you could learn one language right away, which one would you choose and why?
  42. Who would you ask and what would you ask, if you could ask any scientist one question?
  43. Who would you be and what would you do if you could be any historical person for a day?
  44. Which would you rather have: the ability to live without sleep or the ability to sleep as long as you want and always feel relaxed when you wake up?

Funny Questions To Ask In Online Dating

  1. Have you ever liked an old picture or message on your crush’s profile by accident while you were looking at it?
  2. What song would you listen to for the rest of your life if you could only hear one?
  3. What’s the silliest thing you’ve ever bought on the Internet?
  4. If you could be any animal for a day, which one would you be and why?
  5. Which TV show would you choose to live inside for a day and why?
  6. What would you say to a guy in a bar if you wanted to pick him up?
  7. Who do you think you were in a previous life?
  8. Have you ever laughed so hard that you splashed someone with food or water?
  9. Do you like it when pizza has pineapple on it?
  10. Have you ever fought over food? 
  11. How do you feel when people in a restaurant sing “Happy Birthday” to you?
  12. Which would you choose: dating the most annoying person you’ve ever met for a month or not dating at all for a year?
  13. What would you change your name to and why, if you had to?
  14. What’s the corniest one-liner you’ve ever gotten on this dating app?
  15. If you were popular, what would your stage name be?
  16. What’s the most stupid thing you’ve said on a first date?
  17. What’s the craziest dress trend you’ve ever followed?
  18. You can only use ketchup, ranch, or hot sauce for the rest of your life. Which will it be?
  19. Would you rather live with someone who farts or someone who snores?
  20. What would you be bad at if you were a superhero?
  21. Which job would you choose if you had to choose between being a professional clown or a professional mime?
  22. What’s the most stupid mistake you’ve made with your clothes?
  23. Do you know how to make a TikTok dance?
  24. Who would be the worst person to be stuck in an elevator with?
  25. Are you ashamed that you’re using a dating app?
  26. My dog looks exactly the same as yours. Do you think (insert picture of dog) they’re related?
  27. If you could go back in time to any point in history, when and why would you go there?
  28. You want someone to kill bugs for you, right?
  29. Which social media site would you use for the rest of your life if you could only use one?
  30. What was the first picture you put up on your wall when you were a kid?
  31. One of the best questions to ask on a first online date is, “What’s the weirdest thing you’ve ever eaten?”
  32. What would you eat for the rest of your life if you could only eat one thing?
  33. Who would you be and why, if you could be any character from a book?
  34. What would you call peanut butter if you didn’t call it peanut butter?
  35. Would you rather be stuck on an island with a famous person or a character from a book?
  36. What’s the craziest thing you’ve done to try and impress someone?
  37. What tool would you use if you were a character in a video game?
  38. What movie would you watch for the rest of your life if you could only watch one?
  39. What would you choose if you could have any ability, but it had to be completely useless?
  40. If you could, would you spend the night in a scary house?
  41. What’s the most strange thing you’ve ever looked up on Google?

Funny First Date Conversation Starters Questions

  1. What would you tell your young self if you could go back in time?
  2. When you were in grade school, were you weird or cool?
  3. Give me one food you would never try, even if someone paid you $100 to do so.
  4. If you could only eat one food for the rest of your life, what would it be?
  5. What would you choose if you could have an unlimited amount of one thing for the rest of your life? 
  6. What would you rather do: be a fly on the wall of the White House for a whole day or a gardener at the White House for a whole week?
  7. Who would you choose to have dinner with from history, and why?
  8. What is your ideal trip or break, and why?
  9. If you could only keep three apps on your phone, which ones would they be?
  10. What is the most interesting thing about what you do for a living?
  11. What’s your favorite odd mix of foods?
  12. Where would you go and why if you could go anywhere in the world right now?
  13. What bugs you the most?
  14. Do you like to try new places and foods? What kind of food do you like best?
  15. What’s the riskiest or most unexpected thing you’ve ever done?
  16. Have you ever gone somewhere alone? If you haven’t, would you ever think about it?
  17. What’s the worst reason you’ve ever given for not going to work?
  18. Invasion of zombies. Who are your three defense team members?
  19. Have you ever had a pet or do you have one now?
  20. Is your car or your bedroom cleaner?
  21. Which book, movie, or TV show is your favorite, and why?
  22. What was the funniest hurt you ever went to the hospital for?
  23. What’s the worst joke you’ve ever heard out of all the old ones?
  24. If you won $10 million in the lottery, would you still work?
  25. Do you think I look like my social media personal picture?
  26. What’s your favorite hobby or activity to do in your free time?
  27. Which do you scratch first if you have an itch in your nose, butt, or eye?

Funny First Date Questions to Ease the Moment

By asking these fun and light-hearted questions throughout your first date, you can make it a place where you and your date can be yourself. These questions break the ice, get rid of awkwardness, and make it easier to talk about more important things. Remember that the point of the first date is to enjoy each other’s company and lay the groundwork for possible future adventures.

  1. What was the craziest thing you ever bought?
  2. What would the name of the movie about your life be?
  3. What’s the strangest thing you do that you quietly like?
  4. What makes you laugh every time?
  5. Which made-up world would you choose to spend a day in if you could?
  6. What’s the strangest combination of foods that you quietly like?
  7. Which movie are you the most ashamed to say you liked?
  8. What’s the strangest thing you’ve brought back from a trip?
  9. How do you usually dance when no one is watching?
  10. Where would you go right now if you could move anywhere?
  11. What would you eat for the rest of your life if you could only eat one thing?
  12. Which would you like to explore more: the deep sea or space?”
  13. How do you feel about pineapple on pizza?
  14. What is your go-to story for a party?
  15. What song line keeps playing over and over in your head?
  16. If you wanted to get out of this date without being rude, what would you do?
  17. What was your favorite show when you were a child, and do you still watch it?
  18. What’s the worst thing you’ve ever done in terms of social norms?
  19. What was the most ridiculous rule you had to follow when you were young?
  20. What would you do for a day if you could do any job?
  21. What would your superpower be and why, if you were a superhero?
  22. Who would play you in a show about your life?
  23. What device would you miss the most if you had to give it up for a year?
  24. What song on your playlist makes you feel the most ashamed?
  25. How bad was the worst first date you ever went on?
  26. Who in history would you choose to have dinner with if you could?
  27. What was the funniest thing you ever did when you were drunk?
  28. What is your best thing around the house?
  29. Which meme would you be if you were one?
  30. Which animal would you want by your side if they could talk?
  31. What’s something in your pocket or bag that would make me laugh right now?
  32. Which would be a better way to start an awkward talk here: the weather or the food?
  33. Do you believe in aliens? If you met one, what would you do?

FAQs on Funny Questions for First Date 

Q: Can I use these questions on a first date that takes place online?

A: Yes, of course! Whether you’re meeting in person or online, these questions work like a charm.

Should the only things I ask on a first date be funny ones?

A: Funny questions are great, but you should also ask some questions that make you think.

What should I do if my date doesn’t find jokes funny?

A: No problem! Watch how they react and change your method based on what you see.

Q: Can I ask these questions again on the next date?

A: You can add to them or talk about something new to keep the chat going.

Q: Is it okay to also ask about personal things?

A: Yes, but make sure you and your date are both relaxed and don’t cross any lines.

Conclusion

We hope you liked our content and now you are little more confident on going for the first date. If you liked our content then dont forget to visit Go Digital Mag for daily funny and entertaining content.

Vijay Chauhan

Vijay Chauhan is a professional SEO & Content writer at Go Digital Mag and Indiantripster. He is a big Anime & Movie lover. He likes to watch these shows and writes about them. Apart from these he is professional digital marketer who loves travelling and food. Vijay loves to explore new places and shoot videos to post reel on his instagram to share all these amazing places to the world. You can contact Vijay Chauhan on Instagram & Linkedin.

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