20 Questions to Ask a Guy or Girl to Truly Know Them

Updated on August 18, 2019
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Sam wishes you happiness forever in your relationship. And if you aren't in one yet, it will be OK! Everybody's been there.

In the regular 20 questions game, one player thinks of something and then everyone in the group takes turns asking questions so they can deduce what the person is thinking of and make a more educated guess. This version is a bit more exciting in that you get to ask twenty essential questions in order to truly understand who someone really is on a deeper level. Below I’ve included six sets, for a total of 120 questions.

20 Questions to Ask a Crush

  1. What do you think about when you’re trying to fall asleep?

  2. What’s the first thing you look forward to when you wake up in the morning?

  3. What was the last thing that made you laugh?

  4. What does your ideal guy/girl look like?

  5. What qualities must your ideal girl/guy have?

  6. What would you buy for someone you really cared about for their birthday?

  7. What’s the latest I could call you at night that you would still answer?

  8. If you liked someone, how would you let them know?

  9. Do you ever dream about people you know?

  10. What is your idea of a perfect date?

  11. Would you kiss someone on the first date?

  12. If you had a crush on someone, who among your friends would be the first to know?

  13. What’s something that scares you in a good way?

  14. What name do you think is pretty?

  15. Blonde, brunette, or redhead?

  16. Do you prefer girls/guys with makeup or no makeup/styled or natural hair?

  17. What’s the most romantic song on your playlist right now?

  18. What’s something unusual that you like?

  19. What’s something you think people don’t do often enough?

  20. What’s actually harder to do than people think?

20 Questions to Ask a Guy

  1. If the world was coming to an end tomorrow and you could choose only two people to save, who would they be?

  2. What is your favorite memory from your childhood?

  3. What is the thing you’re most thankful for and that you would never want to lose?

  4. Have you ever had your heart broken?

  5. If you had all the money in the world, how would you spend your day-to-day life?

  6. What scares you the most about your future?

  7. How would you describe your ideal life partner?

  8. What was your first crush like?

  9. Do you like kids or pets more?

  10. What scares you most about death?

  11. If you could marry more than one person, would you?

  12. What does third base mean to you?

  13. You’re on a deserted island and a genie appears offering 3 wishes. What do you wish for?

  14. What is one thing that will always make you smile no matter what?

  15. Do you believe in fate?

  16. What is your proudest accomplishment?

  17. Do you feel like something is missing from your life?

  18. What is something you would change about yourself?

  19. If you could relive an age, which age would you choose?

  20. What brings you to tears?

20 Questions to Ask a Girl

  1. What is something you regret not having tried?

  2. With whom do you feel like you can be yourself?

  3. What quality do you admire most about your best friend?

  4. What would make you fall out of love with someone?

  5. If money didn’t matter, what would be your dream job?

  6. What’s more important to you: intelligence or a sense of humor?

  7. What is your favorite book and why?

  8. Are you more liberal or conservative?

  9. Is money or power more important to you?

  10. Do you follow your heart more or your head more?

  11. What's something everyone should try at least once?

  12. If you had $1 million to donate to any charity in the world, which one would you donate to?

  13. Who is your favorite singer/band/musical group?

  14. Do you believe in second chances?

  15. Have you ever thought about what names to give your future kids?

  16. What memory do you wish you could erase from your head?

  17. Have you ever resisted temptation?

  18. Are you more attracted to brain or brawn?

  19. Would you consider yourself more spiritual or religious?

  20. Would you spontaneously take a trip with someone you just fell in love with?

20 Deep Questions to Get to Know Someone

  1. What is one mistake you could never forgive in a relationship?

  2. How much money would you need to be happy?

  3. Is happiness the end-all-be-all or is there something else humans should strive for?

  4. Name five reasons you have to love your life.

  5. Do you believe people should have freedom of speech even if it’s hate speech?

  6. If you had to choose between saving your mom or your dad, who would you choose and why?

  7. If you fell in love with someone else while married with kids, would you leave your family to be with that person?

  8. How would you feel if you found out your parents weren’t your biological parents?

  9. What would you do if you were told you only had a month to live?

  10. Do you think children born today will live better lives than your generation?

  11. How do you feel about cloning other animals for science?

  12. Do you believe there is a higher power in control of your destiny?

  13. What goal should humanity be focused on achieving?

  14. Should people have the right to follow religious practices that could hurt other people (religious views that are discriminatory or demeaning to other groups)?

  15. What's the biggest secret you've ever kept?

  16. If you knew that something you do that makes you happy causes someone else pain, would you keep doing it?

  17. What is something you wish you had more time to do?

  18. What is something you wish you had enough money to do?

  19. What is something you wish you had enough courage to do?

  20. If you could go back in time to undo or redo something, what would it be?

20 Questions to Get to Know Someone Over Text

  1. If you got to choose, what foods would be in your last meal?
  2. Do you have a crush on someone at school?
  3. What is the last thing you bought for yourself?

  4. What is your perfect day like?

  5. Who would you call if you were in serious trouble?

  6. What is something that lifts your mood no matter what?

  7. What’s something you love even though (or because) it’s terrible?

  8. Do you sleep on your front, side, or back?

  9. What is your worst nightmare?
  10. How many people have you kissed/hooked up with?
  11. Mac or Windows?
  12. Where is your phone when you sleep?

  13. Where is one place you'd like to go and what would you do there?

  14. What’s something you’d like to see before you die?

  15. If you got to choose your own nickname, what would it be?

  16. Have you done anything illegal?

  17. If you could choose 3 people to spend a two-week vacation with, who would you choose?

  18. Who in your family are you closest to?

  19. Are you more religious or spiritual?

  20. What is something you are glad you did even though you didn’t want to do it at the time?

First Date Questions

  1. Are you more of a sweet tooth or do you like salty foods?

  2. As a kid, what did you want to do when you grew up?

  3. What is your favorite holiday?

  4. What food will you absolutely not eat?

  5. What’s your favorite drink?

  6. What is your favorite book/movie/song?

  7. How often do you see your family?

  8. Were you a quiet kid or a troublemaker?

  9. What’s on your bucket list this year?

  10. What’s something you wish you were talented in?

  11. What’s your favorite sports team?

  12. Do you like cats or dogs more?

  13. Are you more of an outdoors person or an indoors person?

  14. Which part of your body are you most proud of?

  15. What do you think is the ugliest animal in the world?

  16. Do you prefer relaxing with family or friends?

  17. If you could live in another country, where would you want to live and why?

  18. What is your least favorite chore?

  19. Would you rather be rich or famous?

  20. How spontaneous are you on a scale from 1 to 10, 1 being “leaving the house gives you anxiety attacks” and 10 being “you’ll buy a groupon ticket tonight to go skydiving halfway around the world tomorrow?”


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    • dashingscorpio profile image


      23 months ago from Chicago

      Asking questions are a good way to break the ice with someone new. However it's important not to believe everything you're told.

      It's human nature for people to say or do whatever they believe the person they're (infatuated) with wants to hear. Everyone attempts to put their "best foot" forward to impress someone they like.

      Ultimately it takes (time) to truly get to know someone.

      Generally it's not until after there has been an emotional investment or "commitment" made that people start to feel (safe) enough to reveal their "authentic selves" without the fear their mate will leave. In some instances they may no longer care!


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