69 Best Questions to get to know someone deeper

69 Best Questions to get to know someone deeper

Oftentimes people desire more meaningful conversations in hopes to skip the mundane chat and begin to understand someone else and themselves deeply. While it may be difficult for some people to jump right into “Have you ever had your heart so full of someone else you could barely call it your own?” a  revised quote by Liana Radulescu… There’s nothing like a good questionnaire to open the floodgates. 

In this unironic conversation starter of 69 questions to get to know someone deeper we explore love, sex, philosophy and life goals. I swear!! I couldn’t think of ONE MORE question ;)…

These questions are fun when you are starting to get to know someone and want to know them deeper, whether they are lovers or friends. But these questions are also fun when you know someone well and are looking forward to discovering each other in new ways through these thought provoking questions.

Questions about Love

  1. Is there a difference between “in love” and “love” 
  2. When did you learn what love was 
  3. What makes someone fall in love? (romantically) 
  4. What was your longest relationship?
  5. Can love exist conditionally?
  6. What is your love language?
  7. How long does the honeymoon phase last?
  8. How much should each partner contribute to a relationship?
  9. What is the best part of falling for someone?
  10. Have you ever truly been in love?
  11. What makes someone compatible?
  12. Do you believe in love at first sight?
  13. Do you fall in love easily?
  14. Have you ever experienced heartbreak?
  15. Have you ever broken someone else’s heart
  16. Have you ever stayed in a relationship longer than you should’ve?
  17. Would you rather plan the date or would you rather just be responsible for showing up?
  18. Can you be loved/cared for by someone who doesn’t respect you?

Questions about Philosophy

  1. What is your biggest fear?
  2. Do you believe in astrology
  3. What is beauty?
  4. What does happiness look like?
  5. What counts as unforgivable behavior in a relationship/friendship?
  6. Do you believe in second chances?
  7. If you had a superpower what would it be?
  8. Do you believe in gender roles?
  9. Do you believe in women/trans/nonbinary right to abortion(even without reason)?
  10. Do you believe in life after death?
  11. Do you live with any regrets?
  12. Name 5 things you appreciate about the person asking you these questions?
  13. Name 5 things you appreciate about yourself.
  14. What’s something in (your) life that makes you appreciate the human experience?
  15. Do you have preferences for the people you keep in your life?
  16. Do you believe in soulmates?
  17. Is it ever okay to lie in a relationship?
  18. Can you ever truly know a person (last question)

Friendly Reminder – Feel free to jump around and take as much time as you want answering questions and creating follow up questions.

Questions about Goals + Aspiration

  1. Are you self-goal oriented or family-goal oriented
  2. Is there any dream you gave up on but would go back to in a heartbeat if you could? (if so why’d you give it up?)
  3. Where do you see yourself in 5 years?
  4. Do you like to set realistic goals or do you like your goals to be as big as your dreams?
  5. Have you ever felt lost?
  6. What’s your earliest childhood memory
  7. Where would you like to travel?
  8. What is something you are looking forward to?
  9. What is a skill or trait you would like to obtain?
  10. Who is your biggest inspiration?
  11. What are your future career goals?
  12. Describe your perfect morning, how closely does your morning resemble this?
  13. Paint a verbal picture of what your “dream life” looks like
  14. Do you prefer to be well compensated in self-employment/freelance or working for someone else well compensated? (or are you most interested in the dismantlement of capitalism) 
  15. Have you ever stepped on someone else to get where you want?

Questions about Sex

  1. Have you ever faked an orgasm? If so, have you ever had a real orgasm?
  2. What’s a sex fantasy you are interested in exploring?
  3. Have you ever cheated or been cheated on?
  4. What do you consider cheating? (ex. Watching porn/friends of the attracted sex/sexting/etc)
  5. Once a cheater always a cheater?
  6. Where’s a unique place you’ve had sex?
  7. Morning / mid-day / or evening sex?
  8. How often do you think about sex?
  9. Do you regularly get tested?
  10. Do you like making eye contact during sex?
  11. Would you ever attend a sex party?
  12. What’s in your porn search history?
  13. Have you ever had a threesome?
  14. Do you consider yourself kinky?
  15. Do you like talking dirty during sex or do you focus on moaning?
  16. What is your favorite type of foreplay?
  17. When’s the last time you made love?
  18. What is something you want more during intimacy?
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