The case of the tryhard who wants to care less.

Yowei has a problem. She overprepares, overthinks, and gets so caught up in worrying about doing a good job that sometimes it makes her worse at her job

Jay Caspian Kang is a staff writer for The New Yorker and co-host of Time to Say Goodbye. He manages to do serious, thoughtful work, while giving the impression that he couldn't care less what anyone thinks. What's his secret? Can you care deeply about your work without being consumed by whether it succeeds?

Together in this episode, Yowei and Jay explore rejection, ambition, Buddhism, and the surprising costs and benefits of being less attached to outcomes. Plus, Jay shares his recipe for low investment.

From the episode:

• Listen to Time to Say Goodbye, Jay's weekly podcast about politics, culture, fishing, surfing and some other stuff.
• See the photo hanging in Yowei's recording booth and get the low-investment reading list and the photo of Jay in Yowei's recording booth in our free newsletter File Under Feelings. Sign up at proxyhq.org — just click "Join for free."
• Hear more of Jay's advice on speaking bro in a bonus episode of Bad Hang, available to paid members at proxyhq.org.

New to Proxy? Try Bisexual Wife Guy for a classic case, or Yowei Can't Speak Bro, about what happens when friends have different ways of talking and connecting.

Follow us on Instagram — @proxypodcast @yoweishaw

Get in touch — proxythepod@gmail.com

The case of the other woman.

Ellie never thought she’d be the other woman. Then she fell in love with a married man.

In this episode, we find Ellie a proxy: another woman who knows what it’s like to end up in the same impossible position. Together, they talk about shame, responsibility, and what it means to live with a choice you regret when you don’t regret where it led.

Proxy’s fall membership drive is happening now. If you want to help keep the show independent — and get bonus episodes, ad-free listening, live Proxy hangs, and more — become a paid member at proxyhq.org 🍏

New to Proxy? Try Bisexual Wife Guy for a classic case, or Alex's Husband Is Too Straight, about a nonbinary person married to a man who still identifies as straight.

Follow us on Instagram — @proxypodcast @yoweishaw

Visit — proxypodcast.com

Get in touch — proxythepod@gmail.com

The case of the guy who keeps falling for his female friends.

Ryan Jay has a problem. He makes friends with women. They get close. Then he falls for them.

It’s happened enough times that Ryan Jay is starting to question whether he actually knows how to be friends with women without wanting to date them.

So we bring in a proxy to help Ryan Jay figure out why friendship keeps turning into romance for him — and whether there’s another way to do this.

Proxy’s fall membership drive is happening now. If you want to help keep the show independent — and get bonus episodes, ad-free listening, live Proxy hangs, and more — become a paid member at proxyhq.org 🍏

From the episode:

— Andrew Smiler, a licensed therapist and the author of Clinical Work with Men: Understanding Masculinity in Psychotherapy. Find out more about his work at www.andrewsmiler.com.

New to Proxy? Try Bisexual Wife Guy for a classic case, or Taelor Doesn't Want to Have Sex, about an asexual woman trying to figure out how to find the kind of intimacy she wants, without the part she doesn’t.

Follow us on Instagram — @proxypodcast @yoweishaw

Visit — proxypodcast.com

Get in touch — proxythepod@gmail.com

Before Proxy comes back on September 22, Yowei and Kyle hold a tiny business meeting about the state of the show: more listeners, fewer members, a new membership goal, and what it’ll take to make year three. Also, Comcast has thoughts.

The case of the woman about to start medical school who’s scared to ask for help with her drinking.

Chloe loves her life. There’s just one problem: she’s starting to drink more than she wants to, and she doesn’t understand why.

But Chloe is scared that asking for help could threaten the career she’s worked so hard for. So how do you deal with a drinking problem before it becomes an emergency? How do you know when it’s serious enough to do something? And what actually helps people change?

In this episode, we find Chloe a proxy: an addiction psychiatrist who got sober at the same age Chloe is now. Together, they talk about genetics, trauma, secrecy, accountability, AA, and what it takes to address a problem before your life falls apart.

Proxy’s fall membership drive is happening now. If you want to help keep the show independent — and get bonus episodes, ad-free listening, live Proxy hangs, and more — become a paid member at proxyhq.org 🍏

Learn about alcohol treatment:

— National Institute on Alcohol and Alcoholism — evidence-based information about medications, behavioral treatment, and mutual-support options

— NIAAA Alcohol Treatment Navigator — finding quality treatment in the U.S.

— Healthdirect Australia — alcohol treatment and support in Australia

Resources for doctors and medical students:

— Drs4Drs — confidential support for doctors and medical students across Australia

— Australian Doctors in Recovery — confidential peer support for healthcare professionals in recovery

— Federation of State Physician Health Programs — directory of U.S. physician heath programs

New to Proxy? Try Bisexual Wife Guy for a classic case, or Sam Doesn’t Know How to Be Rich, another story about trying to understand a troubling pattern before it turns into an emergency.

Follow us on Instagram — @proxypodcast @yoweishaw

Visit — proxypodcast.com

Get in touch — proxythepod@gmail.com

The case of the asexual woman who wants romantic partnership with no sex.

Taelor wants a partner who wants what she wants: closeness, commitment, emotional intimacy, a life together. Just not sex.

But years of dating as an asexual woman has left Taelor wondering if what she wants is too specific to find. Does she keep trying? And if love without sex isn’t possible for her, how does she cope? How do you grieve a life you still want but aren’t sure you’ll get?

In this episode, we find Taelor a proxy: an asexual woman who's been married for 12 years without having to compromise on sex. Together, they talk about boundaries, loneliness, and how to keep fighting for the love you want when the world keeps telling you your version of it doesn't count.

From the episode:

— The Ace Couple podcast that Courtney hosts with her partner Royce

— Courtney Lane's work as a Victorian hair artist and historian

Funding for this story was provided by the University of California, Berkeley’s Greater Good Science Center, as part of its “Spreading Love Through the Media” initiative, supported by the John Templeton Foundation.

New to Proxy? Try Bisexual Wife Guy for a classic case, or Alex's Husband Is Too Straight, another episode about wrestling with attraction and longterm romance outside the usual script.

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. Become a paid member at proxyhq.org to 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 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. Become a paid member at proxyhq.org to 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. Become a paid member at proxyhq.org to 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