Heather Havrilesky is the popular and beloved creator of the “Ask Polly” advice column, which she has just moved to Substack after a long run in New York Magazine. Meghan invited Heather onto the podcast to talk about the legacy of “Ask Polly,” the creation of Polly’s alter ego in the advice giving world, "Ask Molly,” and about how she came to be an existential advisor to people who feel lost in the world or confused by life. This interview is a little different from the usual Unspeakable fare. Meghan and Heather have been friends for a long time and have had some differences over the last couple of years over culture war issues such as #MeToo and whether misapplied intersectionality is impeding public discourse. (You can probably guess what Meghan thinks.) They get into some robust disagreement in this conversation, so fasten your seatbelt. Don’t worry, everyone gets home safe.
Heather Havrilesky writes the "Ask Polly" advice columnist on Substack and is the author of What If This Were Enough (2018), How to Be a Person in the World (2016), and Disaster Preparedness (2010). She also maintains the Ask Molly newsletter, written by Polly’s evil twin, and has written regularly for New York Magazine, Bookforum, the New York Times Magazine, The Awl, and several others.