Anna Konkle

Anna Konkle

From Reclaiming with Monica Lewinsky by Wondery

May 5, 2026 · 1h 9m · Episode 65

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

More episodes of Reclaiming with Monica Lewinsky

Explore listener stats, chart rankings, contacts and more on the Reclaiming with Monica Lewinsky podcast page.