Vulnerability Questions

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.

(Credit to Evy Kassirer and Jackie Luo for most of these questions)