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.

Comedian and writer Aparna Nancherla discusses her memoir Unreliable Narrator and why her mother made her order pizza to combat her shyness; stand-up comedian Gary Gulman riffs on the false notion of dangerous scissors in elementary school; singer-songwriter and historian No-No Boy performs his song "1603," featured on his latest album Empire Electric, which tells the story of the first non-Native sighting of Oregon by a multicultural crew of sailors who fell through the cracks of history. Plus, host Luke Burbank and announcer Elena Passarello learn about the times our listeners suffered from impostor syndrome.

Cartoonist Emily Flake (The New Yorker) reveals Joke in a Box, her 70-card deck of creative prompts, which results in some live cartooning from the stage; writer and artist Tessa Hulls discusses her graphic memoir Feeding Ghosts, which looks at the three generations of Chinese women in her family; and indie pop duo Pure Bathing Culture perform "The Memento" from their latest album Chalice. Plus, host Luke Burbank and announcer Elena Passarello tells us some favorite (short) jokes.