2025 Update: Leif + A Conversation with Anna Konkle

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.

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