The Toast – "Claud and Friends with Margo Oshry"

Host: Claudia Oshry (Claud)
Guest Co-host: Margo Oshry
Release Date: October 27, 2025
Podcast Network: Dear Media

Episode Overview

This episode marks the launch of the "Claud and Friends" era of The Toast, as Jackie ("Jax") goes on maternity leave. Claudia ("Claude") is joined by her sister Margo Oshry ("Satchel," "Satch," "Crutch," "Patch") for a lively, sibling-focused episode. They dive into family banter, pop culture hot topics, and their personal lives, maintaining the podcast's signature irreverent and playful tone.

Main Themes & Format

• Sisterly Banter & Family Dynamics: Claudia and Margo’s sibling dynamic is front and center, filled with teasing, affection, and inside jokes.
• Pop Culture Breakdown: They tackle trending stories, including celebrity dating rumors, reality TV drama, music tours, and beauty industry gossip.
• Personal Anecdotes: Insights into their daily lives, work, and familial relationships.
• Fast Five: A signature segment covering the top five pop culture stories you "need to know."

Key Discussion Points & Insights

1. "Claud and Friends" Kickoff & Sisterly Dynamics

• Claudia celebrates Margo as her first pick, noting that Margo’s previous episode outperformed other guest hosts ([01:09]).
• Claudia's constructive feedback: Margo "swallows whole sentences" by speaking too quickly ([02:10]).
• Warm welcome as they joke about Margo’s work schedule:
  Claudia [02:44]: "Appreciate you taking time off your extremely important corporate job."

2. Woodbury Commons Outing & Dog Drama

• Margo recounts buying Prada boots for Claudia at an outlet: "Prada boots for $340...that's crazy." ([03:26])
• They debate whether it’s reasonable to bring a dog, Magnolia, to an outdoor mall ([04:01]).
• Candidly confronting their mutual annoyance with each other’s dogs:
  • Claudia [05:05]: "It's not that I hate your dog, actually...she's so fucking annoying."
  • They liken Magnolia's presence to overexposed celebrities, e.g. Chrissy Teigen ([06:01]).
• Margo describes her deep attachment and anxiety about Magnolia’s mortality, prompting sibling empathy ([06:47]).
• Notable Quote [06:47]:
  "You're gonna need to put me in an institution...I'm gonna need to be put somewhere." – Margo

3. Q&A Reflections & Sibling Rivalry

• Claudia addresses audience questions about family jealousy over the podcast. Margo claims she and Olivia are "too busy to care" but they all admire aspects of each other’s lives ([09:23]).
• Playful envy:
  Claudia [10:01]: "I am jealous of...how your breasts stand up on their own."

4. Pop Culture Rundown: Fast Five Stories Start ([12:02])

Reality TV & Influencer Giveaways

• Margo discusses the Whitney Levitt/Mark Ballas giveaway drama around Dancing with the Stars ([12:22]).
• They critique DWTS fandom intensity and fairness of pairings, with Claudia noting,
  [13:22]: "A lot of you are deeply unwell."

Dancing With the Stars Hot Takes

• Margo prefers contestant Alex for her "work ethic," and they joke about the "put your whole pussy into it" meme ([15:06]).
• They chat about TikTok-influenced choreography and generational gaps in pop culture references ([16:00]).
• They examine sibling relationships and shifting podcast focus for the episode.

Sophie Turner & Chris Martin Dating Rumor ([23:17])

• Shocked by the reported date:
  Margo [23:53]: "That is so interesting…everyone in Hollywood dates each other."
• Both prefer previous partners and find the pairing mismatched ([24:11], [27:19]).
• Nostalgic admiration for Joe Jonas and discussion of his social media habits ([24:24]).

The Jonas Brothers Tour & Music

• Analysis of their tour strategy and guest appearances (Demi Lovato, Ben Rector, etc. [25:35]).
• Claudia lists favorite new Jonas Brothers tracks ([26:54]).
• Observation: "Jonas Brothers are the Coldplay of our generation." ([25:20])

Hailey Bieber’s Beauty Regimen & Public Persona ([29:56])

• Recap of Hailey’s podcast interview on procedures she’s had done, disclosing only jaw Botox for TMJ and PRP facial treatments ([30:25], [31:05]).
• Both sisters praise Hailey’s personality and liken her public reception to Gwyneth Paltrow’s trajectory ([33:00]–[34:17]).
• Claudia recounts personal encounters with Hailey, reinforcing her down-to-earth nature ([32:11]).

Katy Perry & Justin Trudeau Spotted in Paris ([35:00])

• Surprised reactions as the two are seen together; considers if this is Katy’s "comeback" era ([36:04]).
• Discusses Katy’s previous relationships and her current media image.

Selena Gomez, Francia, and the "Kidney Drama"

• Speculation about the Selena–Francia friendship fallout and why Francia wasn't at Selena's wedding ([49:06]–[50:24]).
• Debate whether Francia was compensated, with Claudia explaining it's illegal for organ donors to be paid in the US ([49:43]).

Hugh Jackman and Sutton Foster Go Public ([51:13])

• First red-carpet appearance as a couple; discussion of age gaps and relationship timelines ([52:01]–[53:00]).
• Lighthearted comparisons to other May–December celebrity couples and reflections on Jackie and Deborra's long-term relationship.

TV Loyalty: "Younger" and Peter Hermann ([54:07])

• Claudia and Margo argue over Team Charles vs. Team Josh for the "Younger" finale ([54:16]–[54:39]).
• Claudia: "Peter Hermann has acted in all your favorite shows."

Taylor Swift "Life of a Showgirl" Rankings ([55:40])

• Claudia and Margo rank their favorite and least favorite songs, providing hot takes ([55:57]–[56:28]).

Memorable Quotes

• Margo [06:26]: "Did I cry myself to sleep last night thinking about the day Magnolia’s gonna die? Maybe."
• Claudia [13:22]: "A lot of you are deeply unwell...I need to go touch grass."
• Claudia [24:11]: "To me, [Chris Martin and Dakota Johnson] are endgame."
• Claudia [33:00]: "Haley is this generation’s Gwyneth Paltrow. I feel like people aren’t ready to talk about that yet."
• Margo [36:38]: "She’s having, like, the Ozempic Steve Levine moment."
• Claudia [49:43]: "You’re actually not allowed to receive money for a kidney...it has to be a donation."
• Claudia [55:57]: "Let’s say on the count of three what we think the worst song on TLoAS is..."

Timestamps for Notable Segments

• [01:09] Claudia reveals Margo’s popularity as a guest host
• [02:10] Constructive critique about Margo’s quick speech
• [03:26] Prada boots outlet adventure
• [05:05] "I hate your dog" candid exchange
• [06:26] Dog mortality anxiety and dark humor
• [12:02] Fast Five pop culture segment begins
• [13:22] Dancing with the Stars "unwell" fandom discussion
• [23:17] Sophie Turner and Chris Martin rumor
• [24:24] Joe Jonas social media/unfollowing story
• [29:56] Hailey Bieber’s plastic surgery revelations
• [33:00] Hailey as this generation’s Gwyneth Paltrow
• [35:00] Katy Perry & Justin Trudeau rumor
• [39:36] "Freakier Friday" review and Jamie Lee Curtis discussion
• [49:06] Selena Gomez kidney donor rift
• [51:13] Hugh Jackman and Sutton Foster debut
• [54:16] "Younger" finale debate
• [55:40] Taylor Swift Life of a Showgirl album rankings

Tone & Language

The episode is energetic, chatty, and filled with affectionate jabs typical of close sisters. The hosts use Gen Z and millennial slang, hyperbole, and plenty of pop culture references.

For Listeners Who Missed It

This episode delivers classic Toast energy: sibling banter, real-life confessions, hot celebrity gossip, and candid opinions on all things pop culture. It’s rich with quotable moments, family in-jokes, and genuine (if dramatic) discussion on everything from dogs and dating to Jonas Brothers nostalgia and Taylor Swift's latest music.

If you’re tuning in for the “Claude and Friends” era, this episode sets the bar high and signals many more lively, unfiltered episodes to come.