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.

DO NOT LISTEN TO THIS PODCAST. Please, we beg you. It's full of juicy, dirty secrets that are not meant for you or anyone else to hear. Don't waste your time listening to this, and whatever you definitely don't share it and don't tell your friends.

Featuring

⁠Raye Schiller⁠

The day on Yenta! pod has finally arrived! Chef Tova Sterling is HERE to talk about her new breakup-sex roleplay kink, stalker fantasies, unholy dating benders, and so much more. Chef Tova is a private chef-turned-internet-personality who built an online empire from behind her cutting board block, whispering about sex while making elaborate food for everyone online who likes to watch ;). While filming this episode in New York City, Raye is joined by guest host and comedian Ariel Elias for a deeply Jewish, deeply horny, and deeply committed-to-the-bit conversation with the creator of Sinners’ Shabbat, NYC’s gloriously sexy collision of Shabbat, burlesque, drag, dancing, and Jewish freaksz.Tova talks to Raye and Ariel about how a psychedelic trip led her to a brief stint at seminary, how she got kicked out of a Jewish professionals group for bringing her femdom friend, and how that moment sparked her to swap traditional Jewish spaces for a 300-person burlesque Shabbat. She also gets into the art of creating an internet persona, her life as a celebrity private chef, and why Jewish references are apparently one of the fastest routes to arousal.Plus: the Jewish boy who wasn’t attracted to her (until he was), Raye coming to terms with being a pillow princess, reading people’s kinks, and the increasingly complicated line between “a little unhinged” and “please change your locks.”Come for the Sinners’ Shabbat lore. Stay for Tova explaining why the right Jewish pervert might just be her soulmate.Follow Tova:Instagram: https://www.instagram.com/cheftova/?hl=enSubscribe to the Patreon for bonus gossip, matchmaking, and the stuff too juicy for the main feed: / yenta Follow Raye:Instagram: / rayeschiller TikTok: / rayeschiller Follow Ariel:Instagram: https://www.instagram.com/ariel_comedy/?hl=enTikTok: https://www.tiktok.com/@ariel_comedyYenta is a Heeb Media podcast. Follow ‪@HeebMedia‬ for more subversive Jewish content.

What even is Jewish food? Is it the dish itself or the love, joy, and obsession people bring it? Does that make Chinese food on Christmas Jewish? Slide into the vinyl seats of the deli booth with Liz Alpern and Jeffrey Yoskowitz of The Gefilteria as they bite into this big, messy question.

Listen to this bonus episode of Meet Me At The Deli, hosted by the co-hosts of our sibling podcast at the Heeb Media Podcast Network. Liz and Jeffrey, friends of the Yenta! pod and experts in the nouveau shtetl lifestyle, get into gut-healthy deli orders, the benefits of being an annoying customer, an amazing restaurant recommendation in Philly, a dog named Challah, and the ethics of the blueberry bagel.

Don’t miss new episodes of Meet Me At The Deli every other Thursday on the Heeb Media Podcast Network.

Show notes:

The Gefilteria’s featured recipes (lots of gluten-free and dairy-free options!): https://www.gefilteria.com/recipes

Chef Ari Miller’s Fishtown restaurant, Post Haste, a favorite of The Gefilteria and a stop on Jeffrey’s trip to Philadelphia: https://www.posthastephilly.com/

This episode was produced by Felicia Reich and edited by Pasha Toub.

Got a burning question about Jewish cooking? Submit your questions at tinyurl.com/GefilteHotline or email podcast@gefilteria.com!

Meet Me At The Deli is co-hosted by Liz Alpern and Jeffrey Yoskowitz of The Gefilteria. Visit gefilteria.com for recipes, workshops, The Gefilte Manifesto cookbook, and more.

This show is an original podcast by Heeb Media, an independent digital nonprofit for subversive Jewish culture. Circumcision not required.

This week on Yenta, we’re joined by Madison Werner — writer, advocate, influencer, glam girl, and the first ever trans Covergirl.We get into:* Madison’s ideal man: masculine, feminine, and proud to show off his trans girlfriend* Gabbing vs. yapping* Lookmaxxing, the manosphere, and men discovering beauty standards* Coming out to gay dads* Kylie lip kits, Madison Beer, and choosing your name from Hashem* Eden Golan’s “Hurricane” and reconnecting to Judaism* Escaping Israel by boat, heartbreak, and rebuilding your life* Internet politics, hate comments, and forcing people to come together through humor* Raye’s new nails and gender euphoria* Antonia’s alleged 100% dark chocolate fraud investigation* Hinge as a trans woman* The life-changing power of getting railed during Yu-Gi-Oh* Sex synesthesia, TV during sex, and radical cunnilingus discourseFollow Madison:Instagram: https://www.instagram.com/madisonwerner/Subscribe to the Patreon for bonus gossip, matchmaking, and the stuff too juicy for the main feed:https://www.patreon.com/yentaFollow Raye:Instagram: https://www.instagram.com/rayeschiller/TikTok: https://www.tiktok.com/@rayeschillerFollow Antonia:Instagram: https://www.instagram.com/antonialastar/TikTok: https://www.tiktok.com/@antonialastarYenta is a Heeb Media podcastTimestamps:00:00 Welcome to Yenta00:24 Madison Warner is here and she is a huge get02:48 Patreon, matchmaking, and Madison’s ideal man04:43 Gabbing vs yapping05:40 Lookmaxxing is basically trans07:55 Madison tells her gay dads she’s trans09:04 Coming out on Facebook in eighth grade10:17 Kylie Jenner, lip kits, and gender awakening13:08 Getting more Jewish and more trans15:29 Madison Beer and choosing the name Madison17:31 Eden Golan’s “Hurricane” changed Madison’s life18:38 Hormones, heartbreak, Israel, and rebuilding20:48 Bigger boobs, more water, and a full life recuration22:12 Jewish day school and the pop-star bar mitzvah22:47 Madison met Kesha at a party26:00 Madison meets Nikki Glaser in West Hollywood27:28 Political advocacy, internet extremism, and the loud 5%31:40 The perfect hate comment33:00 Jewish, trans, and forcing people to come together34:38 Heeb Media and Meet Me at the Deli36:13 To gossip, to gossip36:23 Raye has nails now38:32 The nail tech thought Raye was aristocracy40:48 Nail salons, kidnapping energy, and ethical panic41:39 Madison’s press-on nail wisdom43:20 Dolly Parton, acrylics, and gender performance44:13 Antonia’s dark chocolate conspiracy begins45:09 The 100% chocolate that tasted suspiciously sweet48:17 Antonia calls the chocolate company50:34 The company cancels and the scandal deepens51:47 Madison’s dating life update52:28 Hinge, gender categories, and being upfront53:25 The power of a good getting-down54:41 Hooking up during Yu-Gi-Oh56:23 TV during sex: distracting or perfect?57:45 Sex synesthesia and seeing colors59:32 Madison’s final plugs1:00:54 Patreon and goodbye1:01:16 May your boobs be bigger and may you live your Jewish life