#70 Cayden

As a kid, Cayden was repressed, quiet, and very much closeted. But on a church mission trip, he met Andrew, who inspired him to come out. Now, as an adult, Cayden wants to know what became of Andrew.

Regrets, I've Had a Slew

In February, the Heavyweight team headed to Brooklyn for a live show at On Air Fest. There was a countdown of Jonathan’s most regrettable moments from the show, and an audience Q&A with producers Kalila and Stevie. And fortunately for you, we recorded it all.

Gobi | From This Is Love

We're taking a break to bring you an episode of This Is Love, from the makers of Criminal and hosted by Phoebe Judge. Where Heavyweight explores past regrets, This Is Love looks at the expansiveness of all kinds of love — sometimes love between people, sometimes not.  In June of 2016, Dion Leonard…

#69 Tamara

Tamara and B were best friends and roommates at their Christian boarding school. Then, in 12th grade, a teacher declared B to be possessed by a demon and an exorcism was performed. B and Tamara stopped speaking soon after. Tamara’s worried about B ever since.  If you or someone you know is thinkin…

#68 Songe

When Songe was 8 years old, he made fun of a girl with a facial tic. Just months later, he developed tics of his own—the first signs of the Tourette Syndrome he still lives with today. It felt like cosmic punishment. Songe has wanted to apologize to the girl ever since.

#67 Jenna

When Jenna was eight years old, she was taken from her mom and placed with a foster family called the Grizzles. For two and a half years, she built a life with them, and when they asked to adopt her, Jenna was thrilled. But then, abruptly, the Grizzles changed their minds. Three decades later, Jenn…

Trailer: Heavyweight Season 10

Heavyweight returns on September 17.   Listen wherever you get your podcasts. Pushkin+ subscribers can get all episodes ad-free! Sign up on the Heavyweight Apple show page or at pushkin.fm/plus.

2026 Update: James

James’s father’s dying wish was for his ashes to be spread on the 18th hole of a fancy private golf course. That was 16 years ago. In this episode, James, Jonathan, and their friend Howard attempt a golf heist to get into the club and set things right. In today's update, Jonathan calls up James fo…

Jonathan Vs. Kalila on Smash Boom Best

Jonathan and Kalila go toe-to-toe as guests on the children’s debate podcast, Smash Boom Best, where they debate the merits of phone calls vs. texting. We had a lot of fun doing it, and—if it’s not too bold to presume—we think you will have fun listening to it.

2026 Update: Julia

In grade 8, Julia was bullied so badly by a group of girls that she changed schools without telling anyone. Soon after, the girls from her old school showed up at her house and rang her doorbell. She didn’t answer it. For the past 20 years, Julia’s been wondering what those girls wanted. Ten years…