For the last few weeks, I’ve been surrounded by new people in new environments.

In those moments, I tend to engage in a lot of risk-free small talk: What brings you here? Who do you know? How’s your day going so far.

Only one problem: I hate small talk.

Like a person inching tentatively into a body of cold water, the excruciating search for alignment and overlapping interests feels tedious, protracted, and unnatural.

The conversations that I enjoy the most are the ones that plunge into existential questions about the human condition. They feel risky, refreshing, and reinvigorating.

Only one problem, I’m not very good at initiating.

What questions, prompts, or approaches have y’all found to accelerate depth of connection?