The Toast – “Back to Basics: Wednesday, October 29th, 2025”

Hosts: Jackie Oshry & Claudia Oshry
Episode Date: October 29, 2025
Podcast Network: Dear Media

Episode Overview

In this lively Wednesday episode, Jackie Oshry returns as co-host alongside her sister, Claudia Oshry, for a reunion filled with nostalgia, pop culture, TV recaps, and signature banter. They catch listeners up on Jackie’s maternity leave, recent TV obsessions (especially the latest on Dancing with the Stars), viral weddings, and dish the “Fast 5” stories of the day including celebrity relationship updates, sports news, and the much-anticipated deep dive into Dancing with the Stars: Halloween Night.

Key Discussion Points & Insights

1. Jackie Is Back (and Pregnant as Hell)

• Jackie returns to co-host after starting her maternity leave, revealing her baby is taking its time (“the baby didn’t really get the notice that the leave started” – Jackie, 02:16).
• Claudia teases Jackie for always being drawn back to the mic:

  "You just can’t keep me off this mic." – Jackie, 02:19

• Nostalgic talk about their childhood game, Jacks—complete with a pitch for Tiffany-made sets and sleepaway camp memories.

2. Maternity, Motherhood, and Big Babies

• Jackie shares candidly about late pregnancy, her rare conditions, and the unexpected extension of her maternity leave.
• Clemency for “cervical incompetence queens” everywhere, as Jackie remarks on her resilience:

  "Listen, the fact that you’re a cervically incompetent queen and we’re just making it till the very end—it’s amazing." – Claudia, 04:43

• Jackie discusses her history of having large babies, jokingly campaigns for more credit:

  "I don’t get enough credit for the fact that I birthed Charlie at 9lbs 5oz… That’s crazy stuff." – Jackie, 05:19

3. Dancing With the Stars TV Recap (Starting ~06:00)

• Discussion around “final, final” podcasting before maternity wraps, as Jackie’s appearance coincides with Jennifer Affleck’s DWTS exit.
• Jackie was right about Jennifer Affleck’s readiness to leave the competition:

  "She was not acting like someone who wanted to be voted for… She had her soft smile on all night. She wasn’t even faking the megawatt smile. And I was like, Jen, I hear you. We’re done here." – Jackie, 06:45

4. Ina Garten/Back to Basics Binge & Thanksgiving Planning (09:00)

• Both hosts are deep into Ina Garten: Back to Basics, critiquing wild recipes (sausage and grapes) and production values as seasons progress.

  "Back to basics—and there was nothing basic about that! It was crazy." – Claudia, 08:58

• Jackie reveals she’s hosting Thanksgiving, planning the menu and shopping for autumnal dishware (strong anti-turkey-plate take).

  "Let’s get autumnal plates… that way you can use them for a couple of months." – Claudia, 10:22

The Fast 5 Stories (Starts at 18:29)

1. Jacob Elordi and Olivia Jade Split—for Real This Time (~18:29)

• The split is “over for good.” Claudia is adamant Olivia can do better and credits Jacob for helping rehabilitate her post-scandal image:

  "When we all talk about Olivia Jade, like we don’t even talk about [the college scandal] anymore." – Claudia, 19:07

• Speculation about Olivia’s next romantic chapter, rooting for a “businessman beau” a la Elliot Grainge.

2. Dorothy Wang’s Lavish Italian Wedding & Conversion (~21:25)

• Dorothy Wang (Rich Kids of Beverly Hills and Bling Empire) married Brandon Yankowitz in Florence, with culturally rich celebrations.

• Claudia emphasizes Dorothy's intense wedding prep and "zero notes" on her looks ("if she has no fans, I’m dead… obsessed with her" – Claudia, 22:55).

• Deep dive into Dorothy’s legit conversion to Judaism:

  "She did a hardcore real conversion. She has a Hebrew name. It's Dahlia." – Claudia, 23:21

• Noted absence of Morgan Stewart and possible Rich Kids drama, with speculation over guest list politics.

3. Royals at the World Series: Meghan & Harry’s Low-Key Date Night (~26:40)

• The pair’s attendance brings pop culture visibility to the World Series (“It’s just another Dodgers game”—Jackie, 27:40).
• Both hosts confess to only being aware of the World Series because of this sighting.

4. Taylor Swift Laying Low at Travis Kelce’s Football Games (~31:47)

• Taylor’s low profile attributed to both safety concerns and potential impact on Travis’ performance.

  "It’s like awkward when you get home… She did escape that [curse]” – Claudia, 33:07

• Discussion includes pop culture references to Jessica Simpson/Tony Romo and humorous “plastic surgery hiding” theories (“She’s committing to the bit”—Claudia, 34:33).

5. Dancing with the Stars Halloween Night—Eliminations, Drama, and Major Recap (~42:42)

• Recap covers shocking elimination of Jennifer Affleck, injuries (two contestants hospitalized), the energy of “monster dance-a-thon”, and harsh but fair judging.

  • Notable quotes:

    "If anyone’s allowed to be harsh, it’s [Cheryl Burke]… she was speaking English to me." – Claudia, 43:12
    "I say this all the time. Certain people, when they have, like, a moody dance, they turn the lights—turn the lights on." – Jackie, 43:33

• Detailed rundown of contestants, key dances, voting dynamics, favorites to win, and judge drama—plus fan theories and production gossip (e.g., "Robert and Whitney—ABC would want them to win" – Jackie, 53:02).

Notable Quotes & Memorable Moments

• On Podcasting While Pregnant:
  "It just would be so crazy if you podcasted the day you went into labor. Like, it’s so us." – Claudia, 04:06

• Thanksgiving FOMO:
  "If I get Thanksgiving plates means I’m hosting every year." – Jackie, 10:15
  "Let’s get autumnal plates… the plates still get some use if you make a chili." – Claudia, 10:22

• On Social Media Hate and DWTS Voting:
  "She is getting a lot of hate. It’s so unwarranted… This girl is the best dancer…" – Jackie (on Whitney Levitt), 45:38

• Sausage and Grapes Revelation:
  "I want to know, like, why." – Claudia, 08:52
  "Back to basics—and there was nothing basic about that! Like, it was crazy." – Claudia, 08:58

• On Dororthy Wang’s Wedding Attire:
  "She had to step her pussy all the way up for this wedding. Because, like, those who dish it have to be able to take it." – Claudia, 22:52

Timestamps by Topic

• [00:23] – Jackie Returns from Maternity Leave
• [01:08] – Sleepaway Camp & Jacks Game Nostalgia
• [04:04] – Pregnancy, Labor Watch, and SPD
• [05:05] – Not Getting Enough Credit for Big Babies
• [06:22] – Dancing with the Stars Jen Affleck Deep Dive
• [09:00] – Ina Garten Binging & Thanksgiving Menu Planning
• [13:21] – Back to Basics on HBO Max, Netflix Bans
• [18:29] – Fast 5 Stories Begin
• [18:29] – Jacob Elordi/Olivia Jade Split
• [21:25] – Dorothy Wang’s Wedding & Conversion
• [26:40] – Meghan Markle & Prince Harry at World Series
• [31:47] – Taylor Swift & Travis Kelce: Security, Privacy & Speculation
• [42:42] – Dancing with the Stars Halloween Recap

Flow, Tone, & Final Thoughts

The episode is peppered with witty asides, supportive sisterly ribbing, and pop culture references. Jackie and Claudia switch from deep personal chat (pregnancy, family, holidays) to their signature “girlie” TV analysis and influencer insights. Their dynamic, occasionally finishing each other’s sentences, is lively, candid, and engaging for both dedicated and casual listeners.

Jackie’s participation feels like a “full-circle” moment both for her impending maternity leave and their long-running TV recaps, especially with the DWTS symmetry between Jennifer Affleck’s goodbye and Jackie’s next chapter.

For listeners:
This episode is a balance of easygoing catch-up and incisive pop culture commentary. Expect deep dissection of Dancing with the Stars, honest talk on influencer parenting, inside jokes, and plenty of strong opinions—delivered with the Oshry sisters’ unfiltered energy.

(Advertisements, sponsor reads, and non-content sections have been omitted for clarity and brevity.)