conversation starters for really deep people
I’ve had this running list of my version of the question game for years—just random questions that I ask myself then want to know other’s answers to.
Get to know someone deeper.
what is the best piece of advice you have been given?
what is a mistake you made, that you don’t want others to make?
what is your relationship with your sibling(s)?
who do you look up to the most in life?
what is the biggest lesson you have had to learn?
what is something you are currently learning about yourself?
who was the worst friend you’ve ever had, and how did they change you?
who was the greatest friend you’ve ever had, and why do you want to be more like them?
tell me something someone has told you that you have never forgotten (positive or negative)
how do you want to raise your kids?
how can you be growing in your faith?
does it ever get easier to say goodbye?
why do we create art?
are there parts of your religion that you struggle with or doubt?
what do you want to be remembered by?
are you proud of yourself? why or why not?
do you believe in soulmates— or love at first sight?
where do you think the soul is located in the body?
do you hate or love harder?
what scares you the most about the future?
are you afraid of dying?
if everyone you ever loved was in a room, who would you look for first?
would you rather everyone know everything about you, and have to face their opinion and judgment and misunderstanding, or keep everything hidden but always feel alone?
what are you hesitant to ask me?
where do you do your best thinking/ideating?
what are your expectations in a friend? do you think they are healthy?
what gives your life meaning?
is your mind shaped by addictions, past or present, or free from them?
do you forgive yourself for what you have gone through and the things you’ve done?
do you like yourself/ are you satisfied with who you are?
how do you cope?
what makes you feel truly alive?
when you can’t sleep at night, what is on your mind?
do you feel valued?
do you feel enslaved to money?
what have you had to unlearn?
what struggle have you inherited from your parents?
who do you need to forgive?
what did your saddest moment feel like?
what color is your pain, and where do you feel it in your body?
is love a decision?
what leaves you in awe?
what has felt like the most defining or pivotal moment in your life?
what is a flaw you know you need to work on?
are you happy?