You may know Pete Holmes as the creator, writer, and star of the Judd Apatow-produced HBO series Crashing—the semi-autobiographical series about an aspiring standup comedian whose life turns upside-down when he discovers his wife cheating on him.

As someone who wears his vulnerabilities on his sleeve, Holmes isn’t phased by exposing his personal life to scrutiny: “It feels really good to make jokes, find the lighter side, and share some of the wisdom that comes through painful experiences by bringing them into a story.”

Holmes also hosts You Made It Weird, a podcast dedicated to having real conversations with fellow comedians. The fact that he can start with a question as basic as, “How was finding parking?” and reach something as complex and deep as “What is the meaning of life?” by the end, keeps him, and us, coming back for more.

Holmes joins Off Camera to discuss what it’s really like to get divorced, why a little delusion goes a long way in pursuing your dreams, why being vulnerable is the best way to connect to others, what we can learn from comedians, and why he’ll never tire of having amazing conversations.

As Holmes says, “I feel qualified to talk about Pete Holmes, because I’m Pete Holmes-ing the hell out of this Pete Holmes.” We’re glad we get to talk to an expert.