On this episode of Yenta!, Raye Schiller and guest co-host Gloria Alexander sit down with comedian, writer, and author Amy Silverberg to talk about bisexuality, Jewish guilt, boyfriends—good boyfriends and bad— and the deeply humiliating experience of realizing you might actually be happier when you stop lying to yourself.

Amy gets very vulnerable about her new novel, First Time, Long Time, which she sold after just 30 pages and spent three years losing sleep over, and how writing it forced her to finally tell the truth about her sexuality, her relationship with her father, and all the complicated little contradictions that make up a person. She talks about growing up Jewish in Orange County (so random!), going to church with the Christian kids, joining a hot blonde sorority, secretly asking herself “Are you gay?” in the middle of the night, and eventually realizing that maybe there’s no need to choose a category at all.

Plus: Amy’s first-ever relationship with a woman, her very hot sports guy boyfriend, freezing her eggs, whether babies are compatible with an artistic career, why she’s obsessed with the gray area, the perils of social media, the shocking revelation that astrology apps are mostly written by writers making shit up, and the deeply unhinged story of a first date that ended with a mailbox full of shrimp tails.

Basically, this is an episode about being a person who is still figuring it the fuck out—which, honestly, same!

Chapters:

00:00 — Welcome to Yenta!
02:15 — Meet Amy Silverberg
05:10 — Selling a Novel on 30 Pages
08:42 — Writing Yourself Into the Truth
13:05 — “Are You Gay?”
17:30 — Growing Up Jewish in Orange County
21:15 — The Hot Blonde Sorority Years
25:40 — Bisexuality, Boyfriends & Bad Decisions
31:10 — Dating a Woman for the First Time
36:25 — Do We Really Need to Come Out?
41:05 — Living in the Gray Area
46:20 — Jewish Guilt & Contradictions
51:15 — Writer vs. Comedian
55:40 — The Problem With Social Media
59:30 — Freezing Your Eggs & the Baby Question
01:05:10 — Is Astrology Made Up?
01:08:45 — The Oldest Dog in the World Gets Exposed
01:11:20 — The Shrimp Tail Date From Hell
01:15:00 — Amy’s Novel, Classes & Where to Find Her

Comedian Olga Namer joins Yenta! host Raye Schiller and guest co-host Sarah Afkami for a very hamish episode of Yenta! featuring Olga's nephew Roger, an extra serving of Jewish guilt, and enough gossip to make you want to do teshuvah... again. Olga talks about growing up Orthodox in Midwood, Brooklyn, getting married at 18, becoming a hot divorcee (against her parents’ wishes), and discovering the forbidden delights of non-kosher salad. Plus: the truly horrifying story of the dead rat in her mikvah, the AI girl stealing her jokes and literally her entire face, why she wants to be the female Larry David, and the ex-husband gossip that proves some people really have no shame! We’re talking Syrian Jewish summer culture, and whether Hashem really cares if you turn on a light on Shabbat. You know, the usual.

Chapters

00:00 – Welcome to Yenta! feat. Sarah Afkami, Olga Namer & ...Roger

03:30 – AI is stealing Olga’s jokes, face, and entire identity

09:00 – Growing up Orthodox in Midwood and getting married at 18

15:00 – The first taste of treyf: forbidden salad and the gateway drug to bacon

19:00 – Divorce, dating, and being put on house arrest by your parents

24:00 – The Syrian Jewish community, Deal, and Olga’s comedy origin story

29:00 – Olga’s iconic voice, internet haters, and dreams of becoming the female Larry David

35:00 – When your jokes become your entire personality

38:00 – Comedy, Shabbat, and figuring out your relationship with Hashem

43:00 – The dead rat in the mikvah: a Jewish horror story

51:00 – Mikvah money, Nobu, and other acts of religious creativity

54:00 – Jewish guilt, sexual shame, and being judged for literally everything

1:00:00 – The ex-husband gossip that should have stayed in the group chat

1:06:00 – A Hamptons date, a divorce sob story, and a man who hopes to get hit by a car

1:09:00 – Rosh Hashanah wishes, upcoming shows, and a happy ending

On this episode of Yenta!, Raye Schiller is joined by comedian and honorary Jewess Maddie Walser, with guest co-host Gloria Alexander, for a very horny, very unhinged journey through love, lust, and the internet.

Maddie tells us about all the hotties at the Jewish fraternities, discovering she's a shiksa after dating so many Jewish men in college, and her current situationship, someone she met at Raye’s house on Shabbat who may or may not be ignoring her texts from a boat. Meanwhile, Raye and Gloria reflects on the unpaid labor of dating apps, the lesbian enlightenment that apparently comes from getting your butthole waxed, and that one time Gloria ended up at a stranger's house for Sukkot.

Also, Raye wants a baby??

Subscribe to the Yenta! Patreon for bonus gossip, matchmaking, and the stuff too juicy for the main feed: https://www.patreon.com/cw/yenta

Yenta is a Heeb Media podcast. Follow ‪@HeebMedia‬ for more subversive Jewish content.