
About this episode
Anna Konkle joins Monica Lewinsky to discuss dark humor, grief, and her journey in creating the series PEN15.
Emmy-nominated writer, actor, and co-creator of the critically acclaimed series PEN15, Anna Konkle joins Monica this week on Reclaiming for a conversation celebrating how dark humor can get you through almost anything. Anna retraces her path from a chaotic childhood to co-creating PEN15—a show that lets everyone process the tragicomedy of adolescence. She opens up about a five-year estrangement from her father that ended abruptly when she became his sole caregiver in his final months, and about the ways she’s been able to recategorize her mom—from a source of eye-rolling to a source of admiration. Anna reveals why now was the time to explore grief and reconciliation in her debut memoir, The Sane One, and how the solitary act of writing offered a different kind of healing than collaborative television. Expect a conversation brimming with laughter, warmth and tragicomic story swapping between Monica and Anna. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. Learn more about your ad choices. Visit podcastchoices.com/adchoices
People in this episode
Host: Monica Lewinsky
Guest: Anna Konkle
Topics covered
- dark humor
- grief
- reconciliation
- adolescence
- family relationships
Keywords
- Anna Konkle
- PEN15
- grief
- reconciliation
- dark humor
- memoir
- family
Mentioned in this episode
Books & works: PEN15, The Sane One
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