160+ How Well Do You Know Me Questions: Family, Relationship, And Funny Ones

How Well Do You Know Me Questions - Cover Photo

When life gets boring, we all want to test how well our people know us. Regardless if it’s our lover, best friend, or family member. These questions you’ll find below will make this idea of yours come to life! Not only there are hundreds of them, but they’re divided into categories as well!

Random Questions

This category is excellent to start with, in case you’re curious to know what people know about your hobbies, interests, personal habits, your job, and way more topics. Questions are all safe, so you may also play with your family members. Spoiler alert: you’ll love them!

  1. What is my favorite food?
  2. Who’s the person you looked up to the most while growing up?
  3. What is my favorite type of music?
  4. Am I more of a long-term-oriented person, or more of a live the moment?
  5. What do I think I’m really good at?
  6. Did I ever get in trouble & went to the police while growing up?
  7. What’s my biggest goal in life?
  8. Do I get along well with my work colleagues;
  9. If I had to choose, what would my superpower be?
  10. What do I think is my most annoying habit?
  11. Do I have a dream car?
  12. What’s my favorite nickname?
  13. If I had the chance, would I choose to be famous?
  14. Where did I grow up?
  15. What’s one thing I really like about my job?
  16. Am I a religious person?
  17. Do I have a strict bedtime?
  18. Have I got a driver’s license?
  19. Do I drink alcohol or smoke?
  20. Who was I named after?
  21. What was my favorite TV show back when I was a kid?
  22. Have I ever ridden a horse?
  23. What’s the most embarrassing thing I’ve done in life?
  24. Do I have any side hustle?
  25. What is the first thing I do when I wake up?
  26. What’s my zodiac sign?
  27. What has been a highlight of my life so far?
  28. Am I addicted to anything?
  29. Do I think abortion should be legal?
  30. Am I more of a cat or dog person?
  31. What am I most self-conscious about?
  32. What’s my biggest pet peeve?
  33. Am I scared of any animal or insect?
  34. How many languages can I speak?
  35. What would I choose between money or passion?
  36. What’s my dream vacation destination?
  37. If I had a time machine, what year would I go back to?
  38. Is there any topping I hate having on a pizza?
  39. Which one do I hate most: doing the dishes or cleaning the house?
  40. Do I have any ‘rituals’ I don’t like to skip?
  41. Am I into sports?
  42. What’s my opinion on politics?
  43. Where do I see myself in 5 years?
  44. Am I the eldest or the youngest of my siblings?
  45. What’s my love language?

Questions Related To The Family

Questions Related To Family

Since family is the most important, there’s a special category of questions related to them and your childhood. If the person you’re asking these questions, guesses correctly most of them, it means that they really know you. You’ll probably get to share lots of other stuff among the way too! 

  1. Which sibling am I deeper connected to?
  2. If I had to pick 2 of my family members to o on an island, who would I pick?
  3. Which of my parents was stricter?
  4. How’s my relationship with my grandparents?
  5. Did I have a favorite TV show that I watched over and over again?
  6. Of all my family, who has a personality most similar to mine?
  7. Did I fit the stereotypes about my birth order in my family?
  8. Related to my mom, which household chore am I really bad at?
  9. What’s the biggest challenge my family has faced?
  10. What family traits have I picked up?
  11. What makes me happy?
  12. Do I have a favorite holiday pie?
  13. Have I ever had any near-death experiences?
  14. What was my favorite thing to do growing up?
  15. Who do I call when I need advice?
  16. Did I have a pet when I was a kid?
  17. Was I ‘forced’ to join any sport when I was a kid?
  18. What’s one weird tradition my family still keeps?
  19. If I had one wish for my family, what would it be?
  20. What’s my favorite vacation memory?
  21. What’s my favorite dish my mom cooks?
  22. Was I a more quiet type of kid, or a loud one?
  23. When did I get in the most trouble back then?
  24. What’s the funniest argument we had with our family growing up?
  25. Was I closer to my mom or dad growing up?
  26. What do me and my siblings normally argue about?
  27. Who picked my name?
  28. Did I believe Santa exists?
  29. Do I take leftovers home when I eat out?
  30. What would my parents say is my worst personality trait?
  31. How do I feel about adoption?
  32. What’s one thing in my house I would save in case of a fire?
  33. Do I have any nieces or nephews?
  34. Who was my hero growing up?
  35. Do I have any birthmarks?

Funny Questions

One thing’s for sure: you probably haven’t ever thought of the questions below. They’re hilarious, bring tons of laughs, and let you know the opinions of people while making some unusual conversations.

  1. What’s the weirdest text I’ve ever gotten?
  2. Did I ever catch my parents making love? 
  3. What’s my weirder quirk?
  4. What is something I look really stupid doing?
  5. What childish thing do I still enjoy?
  6. Would I rather have an elephant-sized dog or a dog-sized elephant?
  7. If I were famous for something silly, what would it be?
  8. What’s one non-essential item I would bring with me to an island?
  9. If my life was a movie, would I dare to watch it with my parents?
  10. What do I think of hairy legs?
  11. If I had a pet parrot, what’s the first thing I would teach it to say?
  12. If I came with a warning label, what would it say? 
  13. How do I feel about pineapple on pizza?
  14. What’s my favorite character from The Office
  15. Do I sleep in pajamas or naked?
  16. What’s my favorite corny joke?
  17. What do I think is the dumbest way to die?
  18. What’s my worst dating decision?
  19. Would I rather have hands for feet or feet for hands?
  20. When did I stop believing in Santa?
  21. If I were a chair, which celebrity I’d like to sit on me?
  22. What’s my go-to excuse for canceling plans?
  23. Have I ever pooped my pants as a grown-up?
  24. If I could be a fictional character, who would I be?
  25. Have I ever gone skinny dipping?
  26. What’s the most awkward first date I’ve ever been on?
  27. If I could haunt one person as a ghost, who would I choose?
  28. Did I ever do something embarrassing when I was drunk?
  29. What’s something guaranteed to make me laugh?
  30. What alcoholic drink describes me best?
  31. What qualities in the opposite sex give me ‘the ick’?
  32. If I got to choose my name, what would it be?
  33. Would I rather date a stupid or ugly person?
  34. Do I sleep with lights on or off?
  35. What’s the dumbest injury I’ve ever had?
  36. If I were on death row, what would my last meal be?
  37. When I poop, do I drop my pants around my ankles, or take them all the way off?
  38. What would my three wishes for a genie be?
  39. Do I still sleep with a stuffed toy?
  40. Who do I wish I would torture for the rest of my life?
  41. What’s the fruitless talent I have? 
  42. If I started a Youtube channel, what would it be for?
  43. What would be my weapon of choice in a zombie apocalypse?

Romantic Questions

Romantic Questions

It’s very important to check once in a while how well your lovely partner knows you. To make it a really heart-to-heart session of questions, make sure you both answer the same questions. It gotta be fifty-fifty, right?

  1. Where do I see us in a few years?
  2. What was my first impression of you?
  3. How many people have I dated before you?
  4. Where’s my favorite spot to be intimate?
  5. Am I forgiving?
  6. When did I begin to fall in love with you?
  7. Do I have any insecurity?
  8. What would my perfect getaway look like?
  9. When we are together, what’s one thing I love to do?
  10. Who do I consider my closest friend?
  11. What makes me cry when no one’s around?
  12. What’s my pet peeve in our relationship?
  13. What are the tells when I lie?
  14. How do I like my coffee?
  15. Which habit of yours irritates me?
  16. Do I snore?
  17. Am I afraid of something?
  18. What was I wearing when we first met?
  19. What was my favorite part of our first date?
  20. What are my turn-ons?
  21. Do I like church weddings or private simple ones?
  22. Who was my first kiss?
  23. Other than your physical appearance, name 3 other things I like about you.
  24. What was the first meal I cooked for you?
  25. What’s my love language?
  26. How do I tell you I’m upset?
  27. Would I like to use any toys in the bedroom?
  28. What’s my idea of a perfect date?
  29. How many kids do I want to have in the future?
  30. What’s one gift I’ve gotten from you I love the most? 
  31. Do I have any favorite physical features of yours?
  32. What’s the item I gave you on my last trip?
  33. How many pairs of underwear do I have?
  34. Do I think a distance relationship could work for us?
  35. What’s my biggest goal in life?
  36. Based on you, what’s my greatest weakness?
  37. Do I get easily jealous?
  38. Am I a night owl or a morning bird?
  39. Which colleague irritates me the most?
  40. Describe my ideal wedding.


The thing about these questions is that not only do they tell you how well your people know you, but they also lead to many conversations and storytelling. Whoever’s playing will definitely end up more connected than they were before answering the questions. Life-changing, that’s what they are!

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