The Toast – "Jobbing Our Love"

Hosts: Jackie & Claudia Oshry
Date: Wednesday, October 15th, 2025
Podcast: Dear Media

Episode Overview

This episode dives into the concept of "jobbing your love, loving your job," with sisters Jackie and Claudia Oshry reflecting on work-life balance, sisterhood, and finding joy (and exhaustion) in LA. They discuss everything from personal updates and dog drama to reality TV recaps ("Dancing With the Stars," "The Valley," "Bachelor Mansion Renovation Show") and major pop culture stories, including deep dives into the Victoria Beckham documentary, the Spotify/Netflix podcast deal, and shocking Vanderpump Rules friendship drama.

The tone is classic Toast: playful, witty, slightly self-deprecating, and packed with pop culture snark.

Key Discussion Points and Insights

1. "Jobbing Your Love, Loving Your Job" — Life & Work in LA

• Jackie and Claudia riff on the idea that when you love your job (and your sibling-coworker), every day feels like a birthday (00:39). Loving what you do (and who you do it with) brings energy even to "the worst" days, but LA has its downsides:
  • Claudia is struggling with negative energy in LA and missing her dog, Romeo, which leads to a thoughtful chat about mindset and the power of positivity, especially postpartum.
    • Quote: "When you have a negative mindset, it really affects your reality... you see in the world what’s in your mind." — Claudia (01:53)
  • Jackie suggests Claudia reconnect with nature in LA (Nobu Malibu, convertible, PCH drive) to break the cycle.
  • Banter about taking kids in a convertible and whose child is the real LA baby (03:33).

2. "The Good Guys" Podcaster Rivalry

• Claudia's husband Ben is thriving with his podcast ("The Good Guys"), creating a humorous sibling rivalry:
  • Claudia jokes that she's threatened by Ben's success and juicy interviews (with hints at a John Stamos episode and dramatic Hollywood tea).
    • Quote: "Maybe I’m not the most successful podcaster in my house…" — Claudia (05:36)
• Jackie teases about being left behind if Ben's show continues to blow up.

3. Delays in Pop Culture Consumption: 'Dancing With the Stars' in LA

• The East Coast/West Coast TV airing delay leads to spoilers and frustration for watching "Dancing With the Stars" live (07:23).
• Recap of emotional tributes on the show, including memorable moments like Mr. Feeney’s appearance and standout emotional TikTok montages by contestants (08:46).

4. Celebrity Relationship Analysis: Selena Gomez, Brooklyn & Nicola, and More

• Discussion of reports about Selena Gomez’s drifting friendship with Nicola and Brooklyn Peltz Beckham:
  • Speculation about the reasons for the fallout—who's the toxic one, and which clues suggest red flags.
  • Compare/contrast with Selena’s other friendships (including donors and Disney friends).
  • Segue into the Victoria Beckham documentary:
    • Jackie and Claudia agree the doc was aesthetically pleasing but mostly an infomercial for VB’s brand—gliding over major parts of her life and raising more questions than answers (25:07).
    • Quote: "It was just an advertisement for her brand, and it was a beautiful one at that." — Jackie (24:40)
    • Notably missing: hard details about the Spice Girls breakup.

5. Bravo and Reality TV Scandal

• Deep-dive into the Wendy Osefo insurance fraud allegations:
  • Step-by-step analysis of Wendy and her husband’s alleged scheme—claiming items lost to burglary that were later visible on social media and even worn on camera. Jackie breaks down why this mistake was so "not smart" given Wendy’s image as the “smart” Housewife (15:30).
    • Quote: "Like, I could have committed a better crime." — Claudia (12:16)

6. Reality TV News Bites

- 'Bachelor Mansion Renovation Show'

• Introduction of the new HGTV competition: former Bachelor Nation contestants (including golden Bachelor/Bachelorette alums) competing to renovate the legendary mansion, with Taisha Adams and Tyler Cameron as judges (30:21).
  • Banter about contestants’ actual renovation abilities, with playful skepticism.

- Streaming Updates & Podcasting News

• Apple TV+ rebrands to Apple TV, causing confusion (37:09).
• Netflix to host Spotify video podcasts starting in 2026, setting off a riff about podcast industry trends and "cord-cutter" identities (40:06).
  • Jackie: "We are an independent media company. Not to get ahead of myself, but if we were to be on this program, that would mean the frames would be on Netflix." (41:35)
  • Claudia: "Rising tides raise all shines. This is great for everyone!" (42:28)
  • Amused reactions to the batch of sports-heavy Ringer podcasts as Netflix’s test case.

7. Vanderpump Rules Friendship Fallout

• Hot tea: Lala Kent and Sheena Shea’s friendship is "beyond repair" (48:33):
  • Multiple possible causes: Sheena upset at lukewarm support for her memoir, Lala possibly leaking info about Brock’s affair.
  • Jackie contextualizes the friendship’s depth—these two were "like sister wives," raising children together and sharing real estate—and how surprising this downturn is given their distance from the pressures of reality TV (52:39).
    • Quote: "They were living their lives like, like sister wives... it’s so crazy that that could to be so rocky." — Jackie (52:39)
  • Lala's anxieties about being reality TV villain post-Scandoval discussed.

8. Dancing With the Stars Recap

• Major emotional tribute night:
  • Intricacies (and awkwardness) of three-person dances.
  • Dylan and Daniella scored highest (36/40) with a dance for his little sister (56:12).
  • Robert Irwin’s tribute to his mother was a standout (58:31).
  • Behind-the-scenes cast and family moments, including Alex Earl's blended family (#jawdrop).
  • End discussion full of “slay” and hopes for Golden Bachelorette upgrades and changing reality TV tropes (64:45).

Notable Quotes & Memorable Moments

• "When you love your job and you job your love, every day is the birthday." — Jackie (00:39)
• "When you have a negative mindset, it really affects your reality... you see in the world what’s in your mind." — Claudia (01:53)
• "Maybe I’m not the most successful podcaster in my house…" — Claudia, on Ben’s podcast success (05:36)
• "Like, I could have committed a better crime." — Claudia, on Wendy Osefo’s insurance fraud scandal (12:16)
• "It was just an advertisement for her brand, and it was a beautiful one at that." — Jackie, on the Victoria Beckham doc (24:40)
• "They were living their lives like, like sister wives... it’s so crazy that that could to be so rocky." — Jackie, about Lala & Sheena (52:39)
• "Rising tides raise all shines. This is great for everyone!" — Claudia, about Netflix/Spotify podcast news (42:28)
• "The best part was her making a TikTok with Harper." — Jackie, on Victoria Beckham’s rare ‘real’ moment (29:13)

Timestamps for Important Segments

• 00:00–04:00: Opening banter; “jobbing your love” philosophy, LA woes, dog talk
• 04:35–06:55: Ben’s “Good Guys” podcast rivalry; John Stamos tease
• 07:23–10:16: Struggles with “Dancing With the Stars” schedule, emotional recaps
• 12:16–15:48: Wendy Osefo insurance fraud scandal breakdown
• 21:01–29:13: Selena Gomez/Nicola/Brooklyn friendship drama; Victoria Beckham doc review
• 30:21–36:44: Bachelor Mansion Renovation Show; casting and format
• 37:09–42:38: Apple TV+ rebrand; Netflix x Spotify podcasts; future of podcasting
• 48:35–55:14: Lala & Sheena friendship fallout (Vanderpump Rules)
• 55:37–65:46: Dancing With the Stars full breakdown, family dynamics

Summary Flow and Utility

This episode mixes meaningfully personal conversations (about negativity, postpartum feelings, and familial work bonds) with deep, often hilarious dives into pop culture headlines. The Oshry sisters’ playful, candid banter keeps things lively, while their sharp commentary on reality TV, streaming trends, and celebrity scandals will catch up any pop culture lover on the week's must-know stories.

Whether you're here for Bravo tea, the warmth of their sibling dynamic, or insider takes on podcast and reality TV industry trends, this episode offers a hearty dose of The Toast’s signature humor and insight.