95 Deep Questions to Ask (and Actually Connect)

How to play

1. 1Pick a question from any section below and both of you answer it honestly about yourself.
2. 2Before you reveal, each person guesses what the other one said.
3. 3Score a point for every guess that matches. Talk through the misses, that is where the good stuff lives.
4. 4In Who Knows You Best, you both answer on your own phones, guess each other, and the app tallies your match percentage for you.

Getting started

1. 1.What is something small that made you happy this week?
2. 2.If you had a completely free day with no plans, how would you spend it?
3. 3.What is a topic you could talk about for an hour without getting bored?
4. 4.Who in your life knows you best, and why them?
5. 5.What is something you believed as a kid that you find funny now?
6. 6.When was the last time you felt truly relaxed?
7. 7.What is a compliment you received that you have never forgotten?
8. 8.What does a perfect ordinary day look like for you?
9. 9.What is something you are looking forward to right now?
10. 10.If you could keep only three possessions, what would they be?
11. 11.What is a question you wish people asked you more often?
12. 12.What is something you are slightly obsessed with at the moment?
13. 13.How do you usually recharge after a hard week?
14. 14.What is a smell or song that instantly takes you somewhere else?
15. 15.What is one thing about you that surprises people when they learn it?
16. 16.What is the kindest thing a stranger has ever done for you?
17. 17.If your week had a soundtrack, what would the title track be?

Values & beliefs

1. 1.What is a value you refuse to compromise on, even when it costs you?
2. 2.What do you think makes a person trustworthy?
3. 3.Has a strong opinion of yours ever completely changed? What flipped it?
4. 4.What does success actually mean to you, in your own words?
5. 5.Do you think people are mostly good, mostly selfish, or somewhere in between?
6. 6.What is a rule you grew up with that you have decided to keep?
7. 7.What is a rule you grew up with that you have decided to drop?
8. 8.What do you think you owe the people you love?
9. 9.When is it okay to break a promise?
10. 10.What is something the world treats as normal that you find hard to accept?
11. 11.How do you decide what is worth being angry about?
12. 12.What is a belief you hold that most of your friends do not share?
13. 13.Do you think forgiveness is always the right choice?
14. 14.What is one thing money genuinely cannot fix?
15. 15.How do you want to be remembered by the people who knew you?
16. 16.What does loyalty look like to you in practice, not in theory?

Fears & vulnerability

1. 1.What is a fear you have that you rarely admit out loud?
2. 2.When was the last time you cried, and what was behind it?
3. 3.What part of yourself are you still learning to accept?
4. 4.What is something you are afraid people will find out about you?
5. 5.When do you feel the loneliest, even around other people?
6. 6.What is a mistake you made that still keeps you up sometimes?
7. 7.What do you do when you feel like you are not enough?
8. 8.Is there a conversation you keep avoiding? What is it about?
9. 9.What is the hardest thing you have had to forgive yourself for?
10. 10.When you are stressed, what is the first thing you stop taking care of?
11. 11.What is a fear you have outgrown that used to control you?
12. 12.What makes you feel safe with another person?
13. 13.What is something you wish you could say to a younger version of you?
14. 14.When was the last time you asked for help, and how did it feel?
15. 15.What is a part of your past you are still making peace with?
16. 16.What is something you pretend not to care about but really do?

Love & relationships

1. 1.What made you realize you could trust someone completely?
2. 2.What does love feel like to you when it is going well?
3. 3.What is a small thing a partner could do that would mean the world to you?
4. 4.How do you know when you actually feel close to someone?
5. 5.What did your first relationships teach you about yourself?
6. 6.What is your love language, and how did you figure that out?
7. 7.When you fight with someone you love, how do you usually want it to end?
8. 8.What is something you need in a relationship that you used to be embarrassed to ask for?
9. 9.Who taught you the most about love, for better or worse?
10. 10.What is a deal breaker for you that you did not understand until later?
11. 11.How do you show someone you care without saying it?
12. 12.What is the most romantic thing that has ever happened to you?
13. 13.What does being chosen by someone mean to you?
14. 14.When did you last feel truly understood by another person?
15. 15.What is a habit you bring into relationships that you are working on?
16. 16.What is something you hope the people you love already know?
17. 17.How has your idea of the right person changed over the years?

Life & purpose

1. 1.What were you doing the last time you completely lost track of time?
2. 2.If money were not a factor, what would you spend your days doing?
3. 3.What is something you want to be remembered for?
4. 4.What does a meaningful life look like to you right now?
5. 5.What is a risk you are glad you took?
6. 6.What is a risk you regret not taking?
7. 7.When do you feel most like yourself?
8. 8.What is something you are proud of that you do not get to talk about much?
9. 9.If you could master one skill overnight, what would you choose and why?
10. 10.What problem in the world would you fix first if you could?
11. 11.What is a part of your routine that quietly keeps you grounded?
12. 12.What does the word home mean to you?
13. 13.What is something you used to want badly that you no longer want at all?
14. 14.What is the best advice you have ever ignored?
15. 15.What would you tell yourself if you knew this was a turning point?
16. 16.What gives your life meaning on the days nothing exciting happens?

Past & future

1. 1.What is a moment you would relive exactly as it happened?
2. 2.What is a decision that changed the direction of your life?
3. 3.Who from your past do you wish you had stayed close to?
4. 4.What is something your younger self would be proud of you for?
5. 5.If you could send one message to yourself ten years ago, what would it say?
6. 6.What is a chapter of your life you are glad is over?
7. 7.What do you hope is true about your life in five years?
8. 8.What is a fear about the future you do not talk about much?
9. 9.What tradition do you want to carry forward, and why?
10. 10.What is something you are still hoping to learn or try?
11. 11.If you could keep one memory forever and lose the rest, which stays?
12. 12.What is a version of your future that genuinely excites you?
13. 13.What do you think the older you will thank the current you for?
14. 14.What is a goal you have quietly given up on, and do you miss it?
15. 15.What would make the next year feel like a good one?
16. 16.If today were a chapter title in your story, what would you call it?

Frequently asked questions

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