Jonathan Goldstein’s podcast, Heavyweight, is a smart and introspective show about revisiting the very moments we wonder about and regret. It’s for anyone who has ever held a grudge, doubted a choice, or imagined how things could have been done differently—and isn’t that every person?

In most of the episodes, Goldstein catches up with people who have shaped his past. He tracks down an ex-girlfriend from his youth, visits a long-estranged uncle with his father, asks an old spiritual mentor he fears he disappointed by not becoming a rabbi, and embarks on other such personal quests. The resulting conversations are often awkward—amusingly and painfully so, depending on the subject—but the storytelling is consistently graceful.

In some cases, Goldstein’s guests are the ones reckoning with the past as he facilitates their meditations and confrontations. In one episode, for example, a woman remembers the cruelty of childhood bullies and contemplates how she responded to this difficult situation.

Even the Heavyweight episodes that, on the surface, may seem lighthearted, speak to the complexities of human relationships and trickiness of determining our worth or success by comparing ourselves to other people. The questions that arise likely resemble those many of us have asked ourselves in some form. Should a rift between family members always be repaired? Why does a romantic rejection from so many years ago still sting? How do abandoned childhood beliefs and dreams relate to the paths of adulthood?

These are indeed life’s heavy quandaries, but Goldstein carries them with a poignant blend of wry humor and vulnerability, and he resists tidy resolutions. Take a listen—you won’t regret it. (Gimlet Media)