Never have I ever Play Now

Why ask questions?

In order to meet new people and strengthen relationships with them, it is important to ask the right questions. While exchanging your darkest thoughts, deepest desires and greatest dreams with each other, you are simultaneously taking the relationship to a whole new level. These questions are ideal conversation starters to dive into a deep talk with the person of your choice.

Our collection of 250+ questions is divided into six different categories, so you can find the right questions for your individual situation. Check them out and have fun!

Our collection of 250+ questions

Let’s start with our collection of 250+ questions to get to know someone better. Firstly, we collected 50 questions to ask a guy and then 50 questions to ask a girl. These two categories are perfect if you want to chat with the opposite gender on a more personal level. I mean, doesn’t every guy want to know what the girl of his dream is thinking? Or every woman what the boy of her dreams is feeling? The third category is filled with questions to ask your friends.

It doesn’t matter if they are old friends or you’ve just met them, you will find out something new. The last three categories are made for real funny, deep, and thoughtful conversations. These thought-provoking and deep questions are made for a night full of talking. And if these six categories aren’t enough for you: In the last list, we collected the 20 best questions for your 20 questions game!

50 questions to ask a guy

  1. What do you find attractive in a woman?
  2. Would you rather always make out for six hours or always have sex for less than 7 minutes?
  3. Would you rather have a bubble bath or a steamy shower?
  4. What turns you on?
  5. Would you make breakfast in bed for a girl you fancy?
  6. What do you love most about sleeping with a girl?
  7. What makes you insecure?
  8. What is it about us girls that makes you so horny?
  9. Would you rather do it with a cousin or be the one to end the relationship with your true love?
  10. How attractive do you think you are on a scale from 1 to 10?
  11. Would you rather be with someone shorter than you or taller?
  12. Which Disney Prince are you?
  13. What’s your definition of a “real man”?
  14. Would you rather have your nude photos sent to your family or all over the internet?
  15. If you were a girl for a day, what is the first thing you’d do?
  16. Would you rather have to wear sweatpants for the rest of your life or never be able to wear sweatpants again?
  17. Would you still like a girl if she was way taller than you?
  18. Are women equal to men?
  19. Would you rather be chronically under-dressed or overdressed?
  20. What is the first thing you notice about a woman?
  21. Which actor would play you in a movie about your life?
  22. Would you rather swim in a pool full of Nutella or a pool full of maple syrup?
  23. What’s the worst and best thing about being male?
  24. Would you rather marry the hottest person alive or marry the smartest person alive?
  25. Would you rather find true love today or win the lottery next year?
  26. What would you do if a guy asked for your number?
  27. Have you ever had a sexy dream?
  28. Would you rather take a body shot or have one taken off you?
  29. What are some unfulfilled things in your life?
  30. Where do you see yourself living when you retire?
  31. What are some of the things you wish a girl knew before dating you?
  32. Would you rather have a child every year for 20 years or never have any children at all?
  33. Who is your dream woman, dead or alive?
  34. What is the meaning of cheating for you?
  35. What do you personally think of your friend’s relationships?
  36. Would you rather be an extra in a really good movie or have a big part in a really bad movie?
  37. What do you think of hairy legs?
  38. Would you rather always have a small rock in your shoes or always have mud in your shoes?
  39. What’s your favorite song?
  40. Would you rather be happy or rich?
  41. Is there something that you’ve dreamt of doing for a long time? Why haven’t you done it?
  42. What’s the sweetest thing you’ve ever done for a girl?
  43. What do you think about having kids?
  44. What does love look like to you?
  45. Would you rather always know what time it is or always have exact change?
  46. What’s one thing about the opposite sex that you’re attracted to?
  47. Would you rather be an unknown superhero or a famous villain?
  48. Would you rather have everyone you know to be able to read your thoughts or for everyone you know to have access to your internet history?
  49. Do you believe in God?
  50. What was the best day of your life so far?

50 questions to ask a girl

  1. What would you do if a girl asked for your number and hit on you?
  2. How do you know when you’re in love?
  3. Would you rather take amazing selfies but look terrible in all other photos or be photogenic everywhere but in your selfies?
  4. Would you rather have a side of dog treats with every meal or a side of cat food with every meal?
  5. What do you think about feminism?
  6. Would you rather forget how to speak or forget how to read?
  7. If you got pregnant today, what would you do?
  8. What are some of the things you wish a guy knew before dating you?
  9. Would you rather break out in uncontrollable dance every time someone hums, or never be able to sing again?
  10. What is the most important thing that guys should understand about the girl, and it seems to you that they do not understand?
  11. Would you rather be in jail for five years or be in a coma for a decade?
  12. What’s your favorite smell?
  13. What’s the worst and best thing about being female?
  14. Would you rather have to wear stilettos to sleep or have to wear slippers everywhere you go?
  15. What’s the worst thing about being in a relationship?
  16. Would you rather have it with the lights on or off?
  17. What do you think about marriage?
  18. Would you rather trade some intelligence for looks or looks for intelligence?
  19. Would you still like a guy if he was way shorter than you?
  20. How much honesty do you need in a relationship?
  21. If you were a boy for a day, what is the first thing you’d do?
  22. Would you rather get trapped in the middle of a food fight or a water balloon fight?
  23. What is your opinion on men who refuse to use condoms?
  24. Would you rather be on top or bottom?
  25. Do you believe that the saying “nice guys finish last” has any truth to it?
  26. Would you date two guys in the same day?
  27. Would you rather eat as much chocolate as you want, forever, without any negative side effects, or receive $1 million?
  28. Which Disney Princess are you?
  29. What are you completely over and done with?
  30. What memory do you just keep going back to?
  31. What are the qualities that you are looking for in a man?
  32. Would you rather go on a cruise with your boss or never go on vacation ever again?
  33. Do you think older men are sexy?
  34. Would you rather be framed for a murder you didn’t commit or frame your best friend for a murder you committed?
  35. Can I call you when I feel like hearing your voice?
  36. Which actress would play you in a movie about your life?
  37. Have you ever had to lose someone close to you?
  38. What’s the last concert you went to?
  39. How attractive do you think you are on a scale from 1 to 10?
  40. Would you rather play chess or checkers?
  41. What’s romanticized in modern culture but really shouldn’t be?
  42. What is the worst thing you’ve ever done in your life?
  43. Do you think bald is sexy?
  44. Would you rather die in 20 years with no regrets or live to 100 with a lot of regrets?
  45. What is the ugliest piece of clothing you own?
  46. What language would you like to speak fluently?
  47. What do you love about yourself?
  48. Would you rather have universal respect or unlimited power?
  49. Have you ever had an unrequited love?
  50. Would you rather die before or after your partner?

50 questions to ask friends

  1. What’s the most illegal thing you’ve done?
  2. Would you rather lose your sight or your memories?
  3. What was the best gift you’ve ever given to someone?
  4. What kind of food would you never try?
  5. What was/is your favorite subject in school?
  6. Would you rather give up air conditioning and heating for the rest of your life or give up the internet for the rest of your life?
  7. What’s your perfect burger?
  8. Have you ever been through an experience that you couldn’t explain?
  9. Would you rather never stop growing taller or never need to sleep?
  10. How many phones have you broken or lost?
  11. What’s the most useless thing you’ve ever learned in school?
  12. Would you rather spend a year at war or a year in prison?
  13. What would the exact opposite of you be like?
  14. How would you save the world?
  15. What scares you the most about the future?
  16. Would you rather have 10 years more with your partner or a one-night stand with your celebrity crush?
  17. What country can you name, but besides the name, you know almost nothing else about?
  18. What is the best advertisement you’ve ever seen?
  19. How would you explain what ‘love’ is?
  20. Would you rather forget your partner’s birthday or your anniversary every year?
  21. What was the worst thing you ever tasted?
  22. What’s one thing that totally relaxes you when you’re stressed?
  23. What’s something you were really stressed about, it turned out to be no big deal?
  24. Would you rather be able to breathe underwater or fly?
  25. What would your dream bedroom look like?
  26. What makes you special and unique?
  27. What were some of the turning points in your life?
  28. Would you rather lose the ability to read or lose the ability to speak?
  29. Would you rather go to the cinema or to a concert?
  30. What was your favorite toy as a child?
  31. What would you grab if your house was on fire?
  32. Would you rather invent a new gadget or discover a new species?
  33. What was the biggest mistake in history?
  34. How did you meet your best friend?
  35. What book did you read more than one time?
  36. What would be your perfect breakfast?
  37. What makes you the angriest?
  38. What keeps you up at night?
  39. Would you rather have every movie spoiled for you before you watch it or not be able to watch a new movie until it’s been out for a year?
  40. Have you ever gotten your heart broken?
  41. Would you rather never be able to leave your house or only be able to be in your house for five minutes at a time?
  42. When was the last time you cried, and why did you?
  43. What age do you wish you could permanently be?
  44. Would you rather have to wash your hair with dish soap or wash your dishes with shampoo?
  45. When does time pass fastest for you and when does it pass the slowest?
  46. What do you like to do that is traditionally considered feminine?
  47. What is the real story behind your last Instagram post?
  48. Who’s your favorite fictional character, and why?
  49. Would you rather walk to work in heels or drive to work in reverse?
  50. What is the most unusual fear you have?

50 funny questions to ask

  1. What is the weirdest dream you’ve ever had?
  2. What was the most embarrassing moment of your life?
  3. Have you ever had a crush on an animated character?
  4. What alcoholic drink best describes your personality and why?
  5. How long would you survive a zombie apocalypse?
  6. What have you done wrong for most of your life and only recently found out the right way to do it?
  7. Would you rather have a photographic memory or an IQ of 200?
  8. Would you rather slowly walk across red hot coals or put your hand on a hot iron for 10 seconds?
  9. What TV shows did you watch when you were a kid?
  10. What’s the most ridiculous thing you have convinced someone is true?
  11. What childish thing do you still enjoy?
  12. Would you rather change the outcome of the last election or get to decide the outcome of the next election?
  13. What was your most embarrassing moment in school (so far)?
  14. Would you rather buy all used underwear or all used toothbrushes?
  15. Who’s famous for their talent, but really shouldn’t be?
  16. What’s the worst food combination you can imagine?
  17. Which reality TV series would you love to be part of?
  18. What age do you feel right now, and why?
  19. What’s the strangest hobby you’ve heard of?
  20. Do you believe in aliens?
  21. What’s the weirdest celebrity crush you’ve ever had?
  22. If you could replace the handshake as a greeting, what interesting new greeting would you replace it with?
  23. Would you rather get a paper cut every time you turn a page or bite your tongue every time you eat?
  24. What’s the most ridiculous tattoo you’ve ever seen?
  25. What flavor combination is kind of weird, but you really like it?
  26. What’s the weirdest thing you used to eat as a child?
  27. Would you rather get your paycheck given to you in pennies or never be able to use cash again?
  28. What’s the strangest way you’ve become friends with someone?
  29. What is the craziest thing you’ve ever done?
  30. What’s the most ridiculous argument you’ve had?
  31. Would you rather have to wear stilettos to bed or have to wear slippers wherever you go?
  32. What’s the weirdest conversation you’ve ever overheard?
  33. What’s the strangest gift you’ve ever received?
  34. What’s the most embarrassing thing you’ve ever done to get someone’s attention?
  35. Would you rather only drink water or never eat cookies again?
  36. What is the worst TV show/movie you’ve ever watched?
  37. Which fictional character would you marry if you had the chance?
  38. What’s your most embarrassing sex story?
  39. What are you too old for but still enjoy?
  40. If you were a ghost, how would you haunt?
  41. Would you rather be stranded in the jungle or in the desert?
  42. Would you rather always say what you are thinking or never say anything again?
  43. When and how did you find out that Santa isn’t real?
  44. What was the weirdest habit you had as a child?
  45. When was the most inappropriate time you farted?
  46. Would you rather be a brilliant scientist or a world-famous painter?
  47. What is the best joke that you know?
  48. When was the last time you laughed so hard you cried?
  49. What’s the most ridiculous thing you’ve done because you were bored?
  50. If you could be any animal, what would you be?

25 deep questions to ask

  1. How do you think you’ve changed over the past few years?
  2. Would you rather spend every weekend indoors or spend every weekend outdoors?
  3. What’s the most interesting fact you know?
  4. How would you describe your relationship with your family?
  5. How did you deal with your feelings and emotions growing up?
  6. What was one time you really stepped out of your comfort zone?
  7. Would you rather have a unibrow or a full back of hair?
  8. What’s the most essential part of a friendship?
  9. What is the most important thing you have learned in life?
  10. Would you rather be able to see your own future or be able to see everyone’s future but your own?
  11. What’s the worst advice someone has given you?
  12. What was the happiest moment of your life?
  13. What are you most grateful for?
  14. Would you rather oversleep every day for a week or not get any sleep at all for four days?
  15. What always brings a smile to your face?
  16. Would you rather never remember someone’s face or never remember someone’s name?
  17. How do you deal with difficult situations?
  18. Would you rather go blind young but always have a full head of hair, or go bald young but never lose your sight?
  19. Where do you see yourself in 5 years?
  20. What took you way too long to figure out?
  21. When you were a kid, what seemed like the best thing about being a grown-up?
  22. Have you ever had to lose someone close to you?
  23. Do you have any insecurities in your life?
  24. Would you rather have the legs of a frog or the head of a fly?
  25. If you knew you were going to die in a year, what would you change about how you live?

25 thought-provoking questions to ask

  1. What makes a good life?
  2. Would you rather know all the secrets of space or know all the secrets of the ocean?
  3. What are your views on what happens after you die?
  4. Why do you think we dream?
  5. If you could move anywhere in the world, where would you go?
  6. Given the choice of anyone in the world, who would you want as a dinner guest?
  7. Would you rather meet your favorite fictional character or your favorite musician?
  8. What are the top three things you want to accomplish before you die?
  9. What is your very first memory?
  10. What adventures would you like to have before you die?
  11. Would you rather vacation in the mountains or at the beach?
  12. What do you miss about your childhood?
  13. What do you hate about politicians?
  14. What’s your dream job, and why?
  15. What is the super-power you most want to have?
  16. What are your life’s dreams, and what do you want for your future?
  17. Would you rather always have mismatched shoes or always have mismatched earrings?
  18. If you went into a coma and woke up in the year 2120, what would be the first thing you would want to know?
  19. Would you rather always stink and not know it or always smell something that stinks that no one else smells?
  20. What game or movie universe would you most like to live in?
  21. If you could put something on the cover of a newspaper, what would it be?
  22. What do you really wish you knew when you were younger?
  23. Would you rather sleepwalk every night or sleep talk every night?
  24. If you could see into the future, what’s one thing you want to see?
  25. If you had the super-power of invisibility, how would you use it?

Bonus: The best 20 Questions Game questions

  1. If someone gave you a million dollars right now, what would you spend it on?
  2. Who is the luckiest person you know?
  3. Would you rather have a completely automated home or a self-driving car?
  4. Would you rather marry someone that you don’t love or marry someone that doesn’t love you?
  5. What’s the most paranormal thing that has happened to you?
  6. What do you imagine your future family will be like?
  7. What are some things people have selflessly done to make your life better?
  8. What does your name mean?
  9. What was the best meal you’ve ever eaten?
  10. In your opinion, what is the most useless animal?
  11. What movie have you seen more than seven times?
  12. What’s the most pleasing accent to hear your language spoken with?
  13. What do you think people automatically assume about you when they look at you?
  14. Would you rather never be stuck in traffic again or never get another cold?
  15. What was your hardest decision so far?
  16. Would you rather have a home on the beach or in the mountains?
  17. What is the most beautiful word for you?
  18. What can you talk about all day?
  19. Would you rather be the best at something no one cares about or be slightly above average, but nowhere near the best at something people care about?
  20. Would you rather have all eyes on your or blend into the background?

✍️  May 26, 2020

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Conversation Starters & Icebreakers

The PsyCat Games magazine topic conversation starters & icebreakers is dedicated to the best questions to start a great and interesting conversation for girls and guys. You can also use those questions for your first date or even a reunion with your friends at a party.