2025 Update: Leif + A Conversation with Anna Konkle

2025 Update: Leif + A Conversation with Anna Konkle

Author: Pushkin Industries July 17, 2025 Duration: 55:17

For our penultimate Heavyweight encore, we’re joined by Pen15 co-creator Anna Konkle to revisit last season’s junior high drama — #53: Leif.

On Valentine’s Day in junior high, Leif was supposed to ask Kalila out. But he never did. Leif’s lack of action that day impacted Kalila’s life to come. And so seventeen years later, she wants to know: what happened.

For more, head over to Pushkin+, where you can subscribe to hear an extended cut of Kalila’s conversation with Anna.


Credits

This episode was hosted and produced by senior producer Kalila Holt, along with Jonathan Goldstein and Phoebe Flanigan. The supervising producer is Stevie Lane. Production assistance from Mohini Madgavkar. Editorial guidance from Emily Condon. Special thanks to Max Green, Flora Lichtman, and Connor Sampson. In the IM recreation, Karina was played by Reagan Didier, and Leif was played by John Claassen — thanks to Greg Holt and Tony John for making that possible. The show was mixed by Bobby Lord. Music by Christine Fellows, John K Samson, Blue Dot Sessions, Katie Mullins, Florian Le Prisé, and Bobby Lord. Our theme song is by The Weakerthans courtesy of Epitaph Records.

See omnystudio.com/listener for privacy information.


There’s a particular kind of memory that doesn’t fade-it’s the unresolved moment, the regret that quietly shapes a life. Heavyweight, from Pushkin Industries, is built on the belief that it’s never too late to go back and try to set things right. Host Jonathan Goldstein doesn’t just reminisce; he gets in the car, makes the phone call, and arranges the meeting. Each episode is a deeply human, often surprisingly funny journey into someone’s past to confront a lingering question: an apology never given, a friendship lost over a misunderstanding, a childhood promise broken. The tone here is a unique blend, fitting its categories of Society, Comedy, and Culture-it’s empathetic and thoughtful, yet laced with Goldstein’s wry, self-deprecating humor. You’ll hear the awkward silences, the nervous laughter, and the genuine breakthroughs. This isn’t a podcast about easy answers; it’s about the messy, courageous, and cathartic process of seeking closure, one personal heavyweight at a time. The conversations are intimate, the stories are specific, and the emotional weight is real, making for listening that is both moving and unexpectedly uplifting.
Author: Language: English Episodes: 100

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