Literary It girl Caroline Calloway joins Erin Hosier and Elizabeth Thompson to talk about her father's tragic suicide amidst her viral public shaming in 2019, her obsession with the late Prozac Nation memoirist and Gen X agent of chaos Elizabeth Wurtzel (who Erin knew well as EW's first assistant in 1999), and the generational legacies left by their unknowable fathers (particularly Wurtzel's secret bio dad Bob Adelman). Caroline interviews Erin about the making of Wurtzel's 2001 advice book, Radical Sanity - which is the inspiration for Caroline's latest - and the three discuss the fallout of the daddy issues complicated women inherit from complicated men.

[1:00–12:00] Becoming Caroline Calloway

The rise of Caroline’s Instagram-era fame, her viral captions, and the internet culture that turned her into a lightning rod. Caroline shares how grieving her father led her to a midnight pilgrimage to the Harvard library, connecting with the version of him she loved most.

[12:00–20:00] Scammer and SurvivalCaroline leans into the “scammer” label and reframes it.

[20:00–36:00] Father Fallout

TW: A frank discussion of Caroline’s father’s suicide, mental illness, and the parallels the hosts draw from their own paternal losses.

[36:00–53:00] Ghosts We Can LoveCaroline reads from Scammer, reflecting on the “younger version” of her father she grieves and how memory can be redemptive.

[53:00–1:03:00] The Wurtzel ConnectionErin recounts her friendship with Elizabeth Wurtzel and the confessional literary era of the 90s that reshaped women’s writing, and the tragic true story of EW's secret father

[1:03:00–1:14:00] Literary LineageCaroline explains her obsession with Wurtzel, the artifacts she collected, and why “messy women” matter.

[1:14:00–End] Mentorship, Madness, and MeaningA spirited discussion of mentorship, fandom, and finding beauty in complicated legacies.