Caitlin Flanagan is one of the best essayists in America. She recently joined The Free Press, and I was glad to finally get her on the show. She is funny, opinionated, and not particularly interested in telling you what you want to hear. We started with Los Angeles, where she lived for 35 years before deciding she’d had enough. Flanagan grew up in Northern California thinking she would hate Los Angeles, fell in love with it instead, and watched it become something she no longer recognized. She has a lot to say about how that happened, and about what the homelessness crisis, the Palisades fire, and the general dysfunction of the city government reveal about progressive governance at the municipal level. From there we got into the topics she has spent much of her career thinking and writing about. We talked about the strange cultural moment we find ourselves in where marriage and motherhood seem harder to want than they used to be, and the subsequent growing political divide between young men and young women and what it means for dating. Finally, Flanagan makes her case as to why having children is still the most meaningful thing a person can do with their life. That is classic Caitlin: warmth and clarity in equal measure, on a topic most writers either sentimentalize or avoid entirely.