I want to have deep conversations with people, but often find myself getting stuck in small talk, unable to steer the conversation towards anything I find meaningful or interesting. It’s easy to end up having friends who I only end up making small talk or talking about work with, even if we both want a closer connection.
I think that the fundamental thing that makes this closer connection happen is vulnerability - in order to have a close connection with someone, it’s important to feel comfortable being vulnerable. However, it’s often really difficult to create space for people to be vulnerable! That’s why I have this list of questions that I answer with people to try to create space for vulnerability. I usually will tell people that I have this list, and then let them pick questions off of it if they’re interested.
- What things in your past have shaped the way you see things now or go about your life?
- What do you want to be better at / change about yourself?
- What aspects of femininity / masculinity do you like?
- How much independence did you get from your parents growing up? Do you like the level of independence you had/have?
- What emotion do you feel most often?
- Would you want to be a parent? Why? How would you want to raise a kid?
- What’s the worst thing you’ve done to someone?
- What other career might you have ended up in?
- Should you seek power?
- What do you most like about yourself?
- What do you most dislike about yourself?
- Would you like to be famous? In what way or for what?
- With whom do you have the best connection in your family? Why?
- What do you value most in a friendship?
- How do you hope you’ll change as a person in the future?
- What’s your biggest insecurity?
- What makes you look down on other people?
- What do you think makes other people look down on you?
- How do you assign self-worth?
- What is the personal quality of which you’re most ashamed?
(Credit to Evy Kassirer and Jackie Luo for most of these questions)