The case of the progressive rich guy who doesn’t know what to do with his money.

Sam grew up middle class, built a company, sold it, and suddenly found himself with more money than he ever expected.

But instead of feeling free, Sam feels stuck. He doesn’t want to become the kind of rich person he used to judge. He doesn’t want money to change his relationships. He doesn’t want to hoard it. He doesn’t even want to talk about it.

In this episode, we find Sam a proxy: David Steely, a former millionaire who has since given most of his money away. Together, they talk about secrecy, guilt, redistribution, enoughness, and the morally complicated question: what are you supposed to do when you have more than you need?

From the episode:

— Resource Generation — an organization for young people with wealth and class privilege working toward wealth redistribution

— Showing Up for Racial Justice (SURJ) — a group that organizes white people for racial and economic justice

New to Proxy? Try Bisexual Wife Guy for a classic case, or Mic Chooses the Wrong Life, a story about regret, comparison, and the fantasy of the unlived life.

For episode liner notes, show gossip, and dispatches from the emotions beat, get our free newsletter File Under Feelings at proxyhq.org.

Proxy is an independent show, supported mostly by listeners. Paid members get bonus episodes, ad-free listening, live Proxy hangs, and the satisfaction of keeping emotional investigative journalism alive 🍏

Follow us on Instagram — @proxypodcast @yoweishaw

Visit — proxypodcast.com

Get in touch — proxythepod@gmail.com

The case of the person who worries their husband still sees them as his wife.

Alex is nonbinary, and their husband Henry is a straight cis man. Henry has been supportive through every step of Alex’s transition — pronouns, testosterone, top surgery — but Alex worries: if Henry is straight, does that mean he still sees Alex as a woman?

In this episode, we find Alex two proxies: Elvis, a trans man who transitioned inside his long-term relationship, and Ryan, Elvis’s straight cis husband. Together, they talk about labels, desire, dysphoric sex, and the tender, terrifying question underneath it all: will you still want me if I change?

New to Proxy? Try Bisexual Wife Guy for another story about identity changing inside a relationship, or Yowei Can't Speak Bro, about the emotional rules of people who say “that’s cool."

For episode liner notes, show gossip, and dispatches from the emotions beat, get our free newsletter File Under Feelings at proxyhq.org.

Proxy is an independent show, supported mostly by listeners. Paid members get bonus episodes, ad-free listening, live Proxy hangs, and the satisfaction of keeping emotional investigative journalism alive 🍏

Follow us on Instagram — @proxypodcast @yoweishaw

Visit — proxypodcast.com

Get in touch — proxythepod@gmail.com

The case of the podcast host who can't speak bro.

For the past twelve years, Yowei has been trying — and failing — to have a normal conversation with her husband's best friend. It's not for lack of goodwill. But somehow, every time, they can't find a rhythm. Yowei's theory: he speaks bro, and she doesn't know how.

In this episode, Yowei finds a proxy bro and gets a crash course in bro banter — the hidden rules and emotional logic behind the joking, shit-talking, and conversations that can last for hours without a single life update.

From the episode:

— Jason Stewart — podcaster, DJ, and co-host of How Long Gone. Follow him on Instagram and X @themjeans.

— Scott Kiesling — professor of linguistics at the University of Pittsburgh, whose work explores masculinity and how men use talk to build relationships and their identities. Learn more at sfkiesling.com.

New to Proxy? Try Bisexual Wife Guy for a classic case, or The First Ever Extrovert-Introvert Cage Match for another case about what happens when friends have different ideas of connection.

For episode liner notes, show gossip, and dispatches from the emotions beat, get our free newsletter File Under Feelings at proxyhq.org.

Proxy is an independent show, supported mostly by listeners. Paid members get bonus episodes, ad-free listening, live Proxy hangs, and the satisfaction of keeping emotional investigative journalism alive 🍏

Follow us on Instagram — @proxypodcast @yoweishaw

Visit — proxypodcast.com

Get in touch — proxythepod@gmail.com