If you’re anything like me, you’ve probably spent a good chunk of your adult life avoiding meaningful confrontation and letting awkward situations fester until they’re basically emotional nuclear waste. Well, lucky for us avoidance specialists, Jonathan Goldstein’s “Heavyweight” podcast exists to vicariously resolve our decades-old hang-ups through other people’s journeys.
For the uninitiated, “Heavyweight” is the show where Goldstein, a man whose combination of persistence, social awkwardness, and profound empathy somehow creates magic, helps people confront their past regrets and unresolved mysteries.
In honour of the show’s triumphant return from an extended hiatus, I’ve compiled this list of the best “Heavyweight” episodes that will make you laugh, cry, and experience all kinds of emotions tied to all those deep, funny, dark, and sometimes life-changing regrets you’ve been harbouring.
#12 Jesse
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A quartet of years past, Jesse survived a life-threatening collision with an automobile. Currently, he seeks to locate the vehicle’s operator. His intention: to express gratitude.
#2 Gregor
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Two decades ago, Gregor loaned a few CDs to a musician friend. Those albums played a role in launching his friend’s rise to rockstar fame. Now, Gregor isn’t just looking for credit, he really just wants his CDs returned.
#32 Vivian
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In 1995, Vivian lost her uncle Helio to AIDS. Now, 25 years later, she embarks on a heartfelt journey to find the man who stood by his side in his final days.
#17 Skye
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In middle school, Skye’s best friends suddenly turned on her, scrawling “f*ck you” on her garage door before cutting her off completely. They never spoke again. Now, with her own son about to start middle school, he’s baffled that she never confronted them. Thirty years later, mother and son embark on a journey to finally uncover the truth.
#40 Barbara Shutt
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In the summer of 1968, Jonathan’s mother-in-law, Becky, shared an unforgettable few months with a woman named Barbara. But after that summer, they lost touch. Now, more than fifty years later, Becky uncovers something about Barbara that makes her question if she ever truly knew her at all.
#41 Barbara Wilson
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This is the conclusion of episode #40, *Barbara Shutt*. If you haven’t listened to the first part yet, be sure to go back and start there!
Heavyweight Short: Hallie
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At 17, Hallie had a brief encounter with a stranger who left a lasting impact on her life. Now, ten years later, she’s on a mission to find her.
#19 Joey
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Following a particularly unfortunate experience caused by social miscommunications, Joey has recruited the assistance of Jonathan “Debonair” Goldstein alongside Jonathan’s associate Gregor to recreate and rectify the problematic events of that day.
#52 Lenny
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Jonathan and Lenny were inseparable as kids, but life pulled them in different directions as they grew older. Now, with Lenny facing his final days and longing for companionship, Jonathan decides to reach out and reconnect.
#27 Scott
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Jonathan and Lenny were inseparable as kids, but life pulled them in different directions as they grew older. Now, with Lenny facing his final days and longing for companionship, Jonathan decides to reach out and reconnect.
#49 Another Roadside Attraction
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During Stephanie’s high school years, a mysterious bookstore appeared almost out of nowhere in her small Texas town. But just as suddenly as it arrived, it vanished without a trace.
#24 Jimmy and Mark
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At just 10 years old, Jonathan Marshall embarked on a 240-mile bike journey. Over three days, he and a group of boys crossed two states without any adult supervision. Now, 45 years later, Jonathan still finds himself reflecting on that unforgettable adventure and the friends who shared it with him.
#33 Bobby
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The story behind what’s widely considered the worst McDonald’s commercial ever created—and how Bobby unexpectedly became part of the chaos.
#44 Sara
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Sara got a letter from a woman who shared her name, claiming to be her childhood best friend. The catch? Sara has no memory of this person—not even a trace.
#30 The Marshes
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A tipsy comment led Steve Marsh and his siblings to uncover a secret their mother had hidden for nearly four decades. Now, Steve is determined to support her in addressing the truth.
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