Deep Questions
How long does is take to get to know someone?
According to a recent study published in the Journal of Social and Personal Relationships, researchers posited that it takes roughly:
– 50 hours of time together to move from mere acquaintance to casual friend
– 90 hours to go from that stage to simple “friend” status
– Over 200 hours before you can consider someone your close friend.
While time is certainly one piece of the puzzle, the quality of conversation changes as you move through those phases of a friendship or relationship as well. To really know someone, both individuals have to reach a state of openness and vulnerability, trusting one another to really know who they are.
Our curated list of deep questions was constructed with this process in mind. These topics span a myriad of topics (including core beliefs, fears, insecurities, family dynamics, and more) meant to spark meaningful conversations and deepen personal connections. So open up and dive in! It’s our hope that there is equally something here for the closest of friends or the newest of acquaintances.
And, as always, we extend to you a warm Chatterbox invitation to upvote your favorite questions!
- What is something you’ve done/felt/seen/etc. that you wish you could experience again for the first time?
- What do you think would shock the younger you the most about the older you?
- What area of your life would you most like to improve?
- Have you ever had an epiphany? What was it about, and what sparked the realization?
- What’s a mistake you keep repeating?
- What unpleasant experience are you most proud of yourself for making it through?
- If you could send a one-sentence-message-in-a-bottle to yourself from ten years ago what would it be?
- What was most different about your life one year ago?
- What do you get the most compliments about?
- What is a childhood habit or preference that you’ll never outgrow?
- Ideally, how would you spend your birthday?
- What is the luckiest thing that has happened to you? What is the unluckiest thing that has happened to you?
- What was the happiest moment of your life? The saddest?
- Are you happy with how the year is unfolding?
- What is your biggest non-academic, non work-related accomplishment?
- If you could erase one thing or event from your memory, what would you choose?
- If you could change one thing about yourself physically, what would you change?
- Has anything happened in your life that you felt severely underprepared for?
- What issues or conversations do you go to each of your parents with?
- What physical traits do you share with your relatives? Personality traits?
- If you could retire at 35, how would you spend your time?
- Which of your friends are you the most proud of?
- Who would you most like to get back in touch with?
- What friend are you able to not speak to for a long period of time and then pick up right where things left off?
- If you had to pick one friend to make all your decisions for you who would it be?
- If you could re-do any one year of your life which would it be?
- Is there something about you that people assume because of your appearance or demeanor? What is a trait or preference you have that people don’t expect you to have?
- What is the greatest challenge or struggle you have ever faced?
- Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?
- Do you believe that people can change?
- Do you believe you will accomplish your dreams? Why or why not?
- When was the last time you cried in front of someone?
- When you want to give up what keeps you going?
- Of the people you’ve lost in life, who do you miss the most? What is it about them that you miss?
- What would you say was the most difficult moment of your life so far?
- Who has been the biggest influence on your life? What lessons did that person teach you?
- What are the most important lessons you’ve learned in life?
- What is the worst argument you have ever been in?
- What single event or decision do you think most affected the rest of your life? Was there a turning point in your life?
- What is your biggest academic or work-related accomplishment?
- You’re old and on your deathbed. With your last breath, you may deliver your last words to anyone you know. What do you say and who do say it to?
- Would you choose different life obstacles or keep the same ones you were given?
- What are you bored with?
- Have you ever desired or longed for something, but once you got it, discovered it was overrated?
- When did you realize you weren’t invincible?
- What’s a brief summary of your outlook on life?
- What’s the strangest situation you’ve ever found yourself in?
- If you had to attend a college different than the one you did, where would you have chosen?
- If money weren’t an issue and you had to enroll tomorrow, which PHD program would you choose?
- Have you ever dreamed of starting a business?
- What is a profession you admire but could never be a part of?
- How do you think about porn?
- What was your biggest mistake in how you approached dating?
- How would you approach dating differently if you could start over again?
- Who was your first love? What drew you most to them?
- What are (or were) your dating deal breakers?
- What do you miss about being single?
- Who is the friend that you feel the closest with given how little time you have actually spent with them?
- Who is the easiest person for you to talk to?
- Who is the hardest person for you to be nice to?
- If you could take back any one interaction you’ve had with a friend what would it be?
- What were your dreams like as a child? How often did you have nightmares?
- When did you first feel like an adult?
- What is the most ridiculous thing you believed as a child?
- What is your earliest memory?
- What was your favorite thing about the place you grew up?
- My most most nostalgic meal is _________.
- What part of your body do you have the most issues with?
- What personality profile test do you believe in most?
- How do you approach heartbreak?
- Generally speaking, how much influence do you have on people?
- What one word do you think the people who know you best would use to describe you to a stranger?
- What is something you have outgrown?
- What triggers you most during an argument?
- What is your top priority in life?
- What are you most thankful for?