The Toast – "Thanksgiving Personality Hires with Margo Oshry"

Podcast: The Toast
Host(s): Claudia Oshry (“Claude”) & guest Margo Oshry
Date: November 25, 2025
Episode Theme: Thanksgiving vibes, family dynamics, pop culture “Fast 5” stories, and listener advice (“Dear Toasters”) with sisterly banter and humor.

Episode Overview

This lively pre-Thanksgiving episode brings Claudia together with her sister Margo for an hour of signature banter, celeb gossip, updates on their personal lives, and a holiday-themed advice segment. The hosts dish out their takes on recent pop culture news, detail Thanksgiving plans, and riff on everything from family drama to viral internet moments—balancing comedic self-deprecation with genuinely thoughtful commentary.

Main Discussion Points & Insights

1. Opening Catch-Up & Sisterly Banter

• Fashion Roast: Claudia gently mocks Margo’s office look, joking she “looks like, quite frankly, a high class hooker,” while herself feeling schlubby postpartum ([00:50]).
  • Claudia: “I'm like, fat and ugly in a slob and nothing fits me right now. And you're, like, sitting and gorgeous.” ([01:48])
• Workplace Dress Codes: The sisters riff on how fashion workplaces have different attire norms than corporate—Claudia compares “going to the office” to “going to synagogue” ([01:20]).
• Compliments & Insecurities: They exchange playful envy: Claudia of Margo’s arms, Margo of Claudia’s “luscious and gorgeous” hair ([03:00]).

2. Personal Updates & Recent Events

• CMA Awards Recap: Margo describes her trip to Nashville and attending the CMA Awards, sharing how she felt she looked her best ever there ([04:06]).
  • Claudia notes their track record of “slaying” at country shows; both gush about the casual, welcoming vibe of the Nashville country scene.
  • Margo shares a behind-the-scenes peek at label politics: “There are so many f***ing people on that carpet.” ([05:30])
  • Meeting with artist Jordan Davis (“kind of a Toaster”) is discussed ([06:19]).
• Holiday Decor & Gentile Jealousy: Discussion on Christmas home decor among non-Jews, Margo marvels at a friend’s seven Christmas trees ([07:38]), and the sisters joke about holiday décor lines (“Ribbons of Christ”).
• Podcast Studio Vibes: Claudia praises the new podcast studio's comfort, which lets the sisters bring their “funniest, best self” ([09:10]).

3. Program Updates

• Thanksgiving & Episode Schedule: This is the last episode of the week for Thanksgiving break. Claudia teases a lighter news week, but promises extra “Dear Toasters” advice submissions ([10:02]).
  • “It’s just going to be a little bit of girly girl chit chat today.” ([10:34])

4. Pop Culture Fast 5(4) (segments at ~[17:13])

Story 1: Taylor Swift’s Wedding Rumors & Music Video

• Claudia and Margo break down the rumors about Taylor possibly marrying at Holiday House in Rhode Island, speculating on privacy and logistics ([17:14]).
• They discuss rumors Taylor filmed an “Elizabeth Taylor” music video in London ([20:05]).
  • Memorable quote:
    • Claudia: “Don’t you feel like she’s gotten, like, less secretive?...She used to release a music video and we had no idea.” ([20:41])
• Excited debate about which Taylor songs deserve music videos; mutual disappointment over “Elizabeth Taylor” choice.

Story 2: Celebrity Sighting – Tate McRae

• Margo ran into pop star Tate McRae in the bathroom at an exclusive club ([22:05]):
  • Margo: “I just wanted to know. Like, I’m obsessed with you. Like, you’re an icon. You’re a legend, and you are the moment.” ([22:59])
  • They recap Tate’s hockey-loving dating life and the “Icebreaker” book trend ([23:28]).

Story 3: Emily Mariko's Iconic Pregnancy Announcement

• The internet’s favorite food vlogger announced her pregnancy by referencing her infamous “liquidy pumpkin pie” video—cutting the perfect pie and showing a tiny slice for the new baby ([25:22]).
  • Claudia: “Literally the best pregnancy announcement. Like, you have Internet lore. You’re poking fun at yourself. You’re finally closing the chapter.” ([27:19])
• The sisters marvel at Emily’s viral rise and nonchalant avoidance of monetization.

Story 4: New Year’s Rockin’ Eve Host Shake-ups

• Julianne Hough will co-host with Rob Gronkowski in Vegas; discussion of her chemistry with Ryan Seacrest (her ex), and their views on her hosting ability ([30:30]).
  • Margo: “But, like, is she a good host?”
    Claudia: “She knows her lines, she knows how to read the teleprompter…” ([30:54])

Bonus Story: Lizzo, Ozempic, and Plus Size Representation

• Lizzo claims “plus size women are being erased” in the Ozempic era, writing about it on Substack ([33:59]).
  • Claudia: “Here’s what’s not being said... most people are not fat by choice... Nobody craves to be fat. So when Ozempic came out and it was this actual doable thing... obviously people are gonna take that way out.” ([35:30]–[36:37])
• Nuanced discussion around body positivity, societal pressure, and weight loss drugs.

5. Dear Toasters: Listener Advice (starts ~[38:01])

The quintessential Toast advice segment addresses listener dilemmas with candid, comedic honesty:

1. Awkward Family Thanksgiving Drama ([42:44])

• Listener’s aunt is bringing a man to Thanksgiving—someone the listener used to “regularly hook up with” (!), but the math makes it look like possible pedophilia.
  • Claudia & Margo start by dissecting the math, then exclaim:
    • Claudia: “Sorry. You shouldn’t tell your aunt. You should tell the police because he’s a pedophile.” ([43:32])
  • If it’s a typo, their advice: “Just be honest with your aunt... Don’t talk to this guy.”

2. Charging Family for Thanksgiving Dinner ([45:53])

• A woman’s brother-in-law charges $25 per person for holiday dinners. Is it wrong?
  • Margo: “It is weird, but I kinda get it.”
    Claudia: “Margaret, you’re saying, am I going to a restaurant? I hope not, because you’re only paying $25 for a Thanksgiving feast... hosting is a financial and time burden.” ([46:33])
  • They agree it’s a little off, but understandable.

3. Holocaust Denial Conspiracy Theories in Dating ([49:52])

• Listener’s new boyfriend spouts Holocaust denial conspiracy theories.
  • Claudia (instantly): “Girl, run. Run Joey run Joey, run Joey, run.”
    Margo: “There’s... conspiracy theories I can get on board with. That is not one of them.” ([50:34])
  • Their advice: immediate breakup, donate to Holocaust Education foundation.

4. Is My Hairdresser Avoiding Me? ([52:17])

• Listener worries her hairdresser never uses her for salon Instagram content.
  • The sisters reassure it’s likely not about her looks—could be her hair type or just awkwardness about asking.
  • “Maybe you have three strands—get extensions!” jokes Claudia ([52:43]), with gentle suggestions to offer herself for a reel next time if she wants it.

6. Thanksgiving Plans, “Personality Hires,” and Sister Dynamic

• Claudia and Margo outline Thanksgiving logistics: Jackie (their sister) is host, but recently postpartum.
  • Margo laments Magnolia (her dog) is banned for being “too loud” for babies ([28:02]).
  • Margo and Claudia joke they’ve been invited as “personality hires” purely for vibes—not for actual help ([28:02]):
    • Margo: “I think we’re just there like for fun. Yeah, like personality hires.”
• Discussion: Should they drink at Thanksgiving? Only Claudia has a good reason not to (breastfeeding).
• They close on what they’re thankful for: family, friends, listeners, and “the Lord” ([55:14]):
  • Claudia: “I am thankful to the Lord. The Lord guides me...thankful to all of our listeners.” ([55:39])

Notable Quotes and Memorable Moments

• On Podcast Hosting:
  "You can really relax and just, like, be your funniest, best self.” (Claudia, [09:12])
• On Taylor Swift's Music Video Secrecy:
  “She used to release a music video and we had no idea...she’s just gotten less secure, but I also think she cares less.” (Claudia, [20:41])
• Lizzo and Body Positivity:
  “Nobody craves to be fat. So when Ozempic came out... obviously people are gonna take that way out. That’s okay.” (Claudia, [36:20])
• Dear Toasters Showstopper:
  “Sorry. You shouldn’t tell your aunt. You should tell the police because he’s a pedophile.” (Claudia, [43:32])

Timestamps for Key Segments

• Opening Banter & Fashion Roast: 00:49–03:00
• CMA Awards Recap: 04:06–07:00
• Holiday Decor Chat: 07:10–08:47
• Fast 4 Pop Culture Stories: 17:13–38:01
  • Taylor Swift Wedding/Music Video: 17:14–21:49
  • Tate McRae Sighting: 22:05–24:40
  • Emily Mariko Pregnancy: 25:22–29:12
  • Rockin’ Eve Hosts & Lizzo/Ozempic: 30:30–37:59
• Dear Toasters Advice: 38:01–54:42
  • Thanksgiving Ex Drama: 42:44
  • Paying for Family Holidays: 45:53
  • Conspiracy Theory BF: 49:52
  • Hairdresser Instagram Angst: 52:17
• Thanksgiving “Personality Hires,” Thanks, and Close: 28:02, 55:14

Summary Tone and Style

The episode is an energetic, fast-paced mix of inside jokes, family “roasting,” honest advice, and relatable commentary on both pop culture and real-life dilemmas. Claudia and Margo’s open, unfiltered style provides plenty of laughs and candid takes, making it both comforting and entertaining for anyone craving a “hang out with friends” vibe ahead of Thanksgiving.