Regrets, I've Had a Slew

Heavyweight host Jonathan Goldstein has spent a decade helping strangers confront their deepest regrets. But when he took the stage at Brooklyn's On Air Fest in February, he turned the spotlight on himself, playing clips from his own show and walking through the moments he wishes he could do over. The result is a live episode that functions as both a confession and a meditation on what regret actually is—whether it's a pathology to overcome or something closer to evidence that we're free.

The Seven Regrets

Goldstein's live set is structured around seven "most regrettable moments" from Heavyweight's ten-year run. They range in severity from the merely awkward to the genuinely painful. In the first clip, he calls a 102-year-old woman named Deborah but accidentally calls her Barbara—a name that comes from nowhere, or possibly from the collision of his mother's middle name and a college girlfriend. He is, by his own admission, often unprepared for interviews, "roused from a nap, fingers sticky with grape jelly." In another episode, he derails a painful memory about private school by spending five minutes trying to understand what bloomers are, ignoring his producer's frantic "wrap it up" gestures.