When the writer, radio producer, and humorist Jonathan Goldstein set out to create his Gimlet podcast, “Heavyweight,” whose second season concluded on Thursday, he considered introducing each episode with a subway P.A. system that would talk to him like the voice of God. On the podcast, Goldstein—a longtime producer at “This American Life” whose radio show “Wiretap” aired on the CBC for more than a decade—acts as a kind of social instigator and meddling therapist. With gumption, empathy, and comic awkwardness, he ventures into people’s lives and tries to help them resolve things from the past: an unsolved human mystery, lingering guilt, a falling-out, hurt that’s turned to grievance. The subway-voice idea, he thought, could be both funny and thematic, like Mork talking to Orson. But it was too elaborate. Instead, each show begins with Goldstein calling an old friend, Jackie Cohen, who banters briefly, laughs at him, and hangs up. It’s like a microcosm of the show: Goldstein acts like an entertaining noodge, makes something happen, gives us a laugh. Then we hear the show’s pleasing theme song, “Sun in an Empty Room,” by the beloved Canadian band the Weakerthans, and we feel good.

Last week, I talked to Goldstein at a café of sorts inside a deli near the Gimlet offices, in Gowanus, Brooklyn. Hanging above him was a dusty shrink-wrapped submarine sandwich the length of a hockey stick; schoolkids bustled around, yelling and buying candy. I told Goldstein that the Jackie intros reminded me of a little comic-within-a-comic, like in Tony Millionaire’s “Maakies.” “I think about comics a lot,” he said. “It’s like ‘Krazy Kat,’ where in every panel, the cat gets hit in the head with a brick. That was the thing that made me feel like it’s O.K. to have her hang up on me week after week. There’s something reassuring about knowing where it’s going.”

I had long heard good things about “Heavyweight” but had not listened to it; I was saving it for a time when I could focus. That time came over the Thanksgiving weekend, when I listened to the whole first season, and what existed of the second, in a kind of rapture, often while driving around New England. (Midway through the first season, I pulled off I-91 North, heading northeast through Holyoke; minutes later, I was horrified to discover that I was somehow south of Holyoke, back in Springfield. What had I done?) Goldstein is engrossing—a sharp, confident writer with natural comic timing. When he talks, you listen in state of simmering amusement that frequently boils over. His sensibility seems to say, Sure, I’m absurd—but so is the world, so let’s confront it and enjoy its absurdity together. (Of his collegiate self on a trip to Manhattan: “Getting off the bus at 8 A.M., I tilted my fedora towards my ponytail and took it all in.” At the office, solving a mystery: “Jorge and I spend the afternoon snacking on honeydew slices and sifting through honeydew-juice-soaked letters.”) As I listened, I kept thinking fondly of “Dr. Katz, Professional Therapist,” the animated show in which Jonathan Katz played a therapist, comedians played his patients, and H. Jon Benjamin played his doofus son. There, as here, self-deprecating comedic humility balances the gravity of life, of the things we talk about in therapy or when confronting the heaviness of the past. This tone makes for a satisfying listening experience, neither too earnest nor too cute. The name “Heavyweight,” Goldstein told me, is meant to suggest the emotional burdens that we carry around, as well as “the connotation of the boxer juxtaposed with the connotation of me . . . the non-boxer.”

In the first season, which came out last fall, the stories centered on Goldstein and his friends and loved ones. He began by attempting to resolve a decades-old rift between his father, Buzz, and Buzz’s brother, Sheldon. Both men are in their eighties, and, as Goldstein puts it in the episode, they “still possess voices and temperaments suited to shouting out Brooklyn tenement windows.” They’ve barely spoken in decades, but Goldstein manages to bring Buzz from his home, in Montreal, to Sheldon’s home, in Florida, where they proceed to tell dirty stories, smoke cigars, bicker, grouse, and, prodded by Goldstein (Sheldon: “He asks the weirdest questions. What is he, a broad?”), talk about ancient pains and memories. Once they give in, they make quick progress. The end, in which both brothers feel better, feels like a hard-won minor miracle. Dr. Goldstein is no slouch. When dealing with tough relationship conversations, he told me, recording is helpful. “The microphone is a safety net,” he told me. “It’s like you’re able to turn to the camera as though addressing the viewing audience and say, ‘Do you see what I’m dealing with here?’ ”

The most famous episode of “Heavyweight” is the second of the first season, “Gregor.” In it, Goldstein gets his friend Gregor to reconnect with Gregor’s long-lost friend Moby, to whom he had once lent his collection of Alan Lomax CDs, which Moby had then used to create his album “Play,” which made him a megastar. Gregor is bitter: he never heard from Moby again, he says, and he wants his CDs back. The resolution is as satisfying, provocative, and funny as that between Sheldon and Buzz, and the episode won the Skylarking Award (an award for fun) at the Third Coast International Festival. (Winning makes him uneasy, Goldstein told me: “I do better with failure.”) “Gregor” is the splashiest example of the kind of thing that “Heavyweight” does well, but the other episodes are often just as rewarding, without the dimension of the past taking your generosity and becoming a zillionaire who seems to forget that you exist. The episode “Galit,” in which Goldstein reconnects with his first girlfriend, who’d broken his young heart, was so affecting that after it ended, I paused it, rather than continuing to the next episode, so that I could keep thinking about everything it had riled up in my own mind.

For the second season, Goldstein, having pursued many of the available stories connected to his own life, branched out into some that came from listeners. This process introduced another level of vulnerability, he told me. “Wiretap,” his old CBC comedy show, combined monologues and telephone calls, scripted and improvised, mainly conducted with his parents and friends that he’d known for decades. Several of these people appear in Season 1 of “Heavyweight.” “It felt like my particular skill set, if you want to call it that, was most at the ready with people that I felt comfortable being a nuisance to,” he said. With the second season, he didn’t know if he’d be up for bringing strangers that kind of discomfort. But there was something liberating about it, too. “And, in fact, when things are uncomfortable it sometimes leads to the best moments,” he said.

The second season often has a feeling of exploration, of venturing further into the wider world: Why did a woman’s foster mother make her stop playing basketball in high school? Why was a cancer survivor kicked out of her sorority? In one powerful episode, a man who was seriously injured after being hit by a car four years ago meets the man who hit him—and expresses gratitude. (Wisely, Goldstein brings a therapist to help facilitate.) Listening to it, I was interested and attuned, yet startled when I suddenly became overcome with emotion at a moment of grace. Last week’s show, about a suitcase full of love letters found on a Brooklyn street corner in 1999, begins as a kind of sidewalk “Griffin & Sabine” but ends with what amounts to a twist: the story begins to rebuke Goldstein and his fellow-investigators, as they discover that the writers of the love letters, long over their youthful romance and married to other people, turn out to be fine, and perfectly unsentimental. The past is past, the letter-writers gently explain, and we, via Goldstein and co., are the ones hanging on. (Mork calling Orson: Come in, Orson.)