I first interviewed comedian and writer Josh Gondelman way back in Episode 39, a conversation that took place nearly four years ago. So we had a lot to catch up on. We talk about the world opening back up and how that’s had an effect on Josh’s career and personal life.  I give a shout out to his substack newsletter, and what it feels like to give advice (or more accurately: pep talks) to others. The conversation delves into empathy, social interactions, and the importance of understanding different perspectives. In this part of the conversation, Josh and I discuss the importance of growing and cultivating community. They talk about maintaining friendships and being upfront about friendship intentions. Josh emphasizes the value of being a fan of your friends and using social media mindfully to support and appreciate others. We also touch on the reticence towards earnestness and the societal pressure to be cool or aloof. I do like the zero and five birthdays, and in advance of Josh’s upcoming 4-0, we talk about what that milestone feels like for him. Josh is an amazing talented (and kind) human, and I’m psyched to welcome him back to the show.