Acclaimed writer Cheryl Strayed (Wild, Tiny Beautiful Things) discusses her new personal essay "Two Women Walk into a Bar," which follows her complicated relationship with her late mother-in-law; stand-up comedian Jay Jurden bridges the generational divide with some poignantly hilarious observations on Boomers and Gen Z; and singer-rapper-poet Dessa performs "Hurricane Party" from her latest album Bury the Lede. Plus, host Luke Burbank and announcer Elena Passarello unpack the benign (but complicated) relationships our listeners have with the people from their everyday lives.