The Toast – "The Toothless Wonder"

Podcast: The Toast (Dear Media)
Hosts: Jackie & Claudia Oshry (Claudia co-hosting with husband Ben)
Air Date: Tuesday, November 11, 2025

Episode Overview

This Tuesday’s episode brings Claudia together with her husband Ben, offering a hilarious and revealing catch-up in Jackie’s absence. The show is an energetic swirl through five “fast five” celebrity stories, intertwined with playful marital banter, and Claudia’s epic tale of surviving a root canal. Listeners are also treated to "Dear Toasters," an advice segment, where Claudia and Ben weigh in with their distinct perspectives. The episode showcases a blend of celebrity gossip, candid relationship talk, wellness trends, product recommendations, and authentic personal storytelling.

Key Discussion Points & Insights

1. Weather and Location Banter

• The couple opens with weather shocks: it’s unusually cold and frosty in Florida (00:39), and snowing in New York, which Claudia is “devastated to be missing” (00:52).
• Ben offers the classic New Yorker’s take on snow: “Snow in New York is fun for, like, one second, and then it turns to slush and then you’re like, this place is absolutely vile.” (00:55 — Ben)

2. Friday’s Unexpected Hosts & Internet Comments

• Last Friday, both regular hosts were absent for the first time. Ben and Olivia hosted, which led Claudia to nervously check comments.
• Claudia’s takeaway: “I never got comments so nice about my own show in my whole fucking life.” (02:27 — Claudia)
• Ben brags about their seamless banter, likening it to a “ping pong match” (02:34), brushing off suggestions that he and Olivia should start a cooking podcast.

3. Bert Kreischer Content Mansion & Inspiration Talk

• Ben recalls his excitement at Bert Kreischer's filmed cooking show (03:12–03:51), gushing about Bert’s “content mansion” and kitchen.
• Claudia points out, “You give credit to Bert Kreischer, but I give credit to Bert Kreischer’s wife because, you know, she was like, well, you’re not cooking in my house with all these. Totally buy the house next door, Burt.” (03:54)
• They muse on their celebrity inspirations: Stanley Tucci and Ina Garten come out as gold standards for Ben (04:36).

4. The Wild Root Canal Saga

(Timestamped Subsection: 05:19 – 11:08)

• Claudia details her recent dental crisis which started with a tooth falling out while wrapping a gift at Bloomingdale’s months ago (“a part of my tooth did fall out at Bloomingdale’s,” 05:35) and ended in a surprise root canal.
• The experience was unexpected, as she went in for a suspected cavity and was immediately told: “This is one of the worst things I’ve ever seen. It’s going to be a root canal. And I said, right now?... If I left, I was never coming back. So I was like, you know what? Fuck me up, fam.” (08:44)
• Claudia shares her pain post-procedure, with Ben unhelpfully but comically observing: “You were screaming in pain.” (09:58)
• Claudia’s pride: “I’m not getting enough credit for raw dogging a root canal. Not only did, you know, no headphones. Yes. No TV.” (10:29)
• The couple riffs on dental hygiene: Claudia is “so meticulous about oral hygiene,” but genetics and pregnancy contributed to her issues—she hates the stigma that cavities = lack of cleanliness (11:04).

5. Tongue Scrapers, Wellness, and Oral Hygiene Rivalry

(11:56–14:46)

• Ben recently starts tongue scraping after Claudia bought him a scraper “years ago,” which irks Claudia (“to hear you waxing on like you invented tongue scraping is so annoying.” 13:02)
• Notable quote: “Claudia in another life was a police dog. Let me tell you. Like, she can smell what the neighbor four floors up is cooking for dinner.” (13:17 — Ben)
• Ben claims, “The tongue scraper was invented over 3,000 years ago. The first toothbrush … the 1700s,” insisting on the importance of scraping (14:14).

6. The Gucci T-shirt That Would Not Die: A Marital Anecdote

• Claudia reminisces about a funny gift fail—a limited-edition size-medium Gucci T-shirt that never fit Ben. They tried (and failed) to consign it. (06:13–07:12)

7. "Fast Five" Celebrity Stories

1. Hilary Duff’s Mini Tour (23:25)

• Claudia is unimpressed, Ben is a fan but cautious: “I was ready to go until I heard intimate. Yeah, intimate to me means probably acoustic. I’m not into that.” (24:36)
• The couple sings “Come Clean,” playfully bickering (25:36).

2. Kris Jenner's Iconic Birthday Bash & Deleted Meghan Markle Photo (27:42)

• Meghan Markle attended and was pictured but the Kardashians deleted the photos—prompting spirited speculation about why. Claudia: “Now it’s no secret that they were there. So why the photos would be removed? It does seem like Meghan or Meghan’s team just reached out and asked for the photos.” (28:38)
• Ben on Harry’s presence: “Sounds like he needs neutrophil.” (30:14)
• General consensus: Trying to erase awkward photos backfires, making it bigger news.

3. Kris Jenner’s Facelift & Party Cost (31:03)

• Claudia and Ben commend Kris’s transparency in crediting her plastic surgeon, Steven Levine, who was the “most popular guy at the party.”
• They discuss the evolving honesty of Kardashian-Jenner family about cosmetic procedures. “People have been begging them for years to be honest with us. They look amazing. We just want to know. We’re not asking to judge, we’re asking because we want to copy it.” (32:46)
• Party estimated price: $4–6.5 million, largely due to Bruno Mars’s performance.

4. Sydney Sweeney’s Flop Film ‘Christie’ (37:04)

• Claudia critiques the strategy: “Not everybody can be good at everything… I would love to say that she's killing it… but a lot of her roles are not good.” (40:10–41:02)
• Ben: “She needs a DiCaprio movie, her and Leonardo something… she needs those roles.” (40:51)

5. Robert Pattinson Would Return to Twilight (41:54)

• Robert Pattinson says he would return as Edward Cullen: “Oh, yeah, definitely… It would be fantastic. I enjoy taking roles from younger actors. I want to be 17 again.” (43:38)
• Claudia, a Twilight superfan, champions its cinematic worthiness: “Not only is it incredible, it is the best acting, writing, cinematic… Twilight is like an exercise in excellent acting, excellent producing, excellent directing, excellent location scouting. Excellent.” (44:09)
• Spirited debate: Ben insists the Batman trilogy is superior, to Claudia’s vehement refusal (44:50).

Notable Quotes & Memorable Moments

• On internet critics and Friday’s co-hosts:
  “I never got comments so nice about my own show in my whole fucking life.” — Claudia (02:27)

• On enduring a brutal dental procedure:
  “I'm not getting enough credit for raw dogging a root canal. Not only did [I have] no headphones. No TV.” — Claudia (10:29)

• Ben on tongue scraping enlightenment:
  “I started tongue scraping two days ago, and let me tell you, my breath… I'm scraping my tongue and then I'm using my new favorite mouthwash, Swishables. Unbelievable.” (12:17)

• On Kardashians and transparency:
  “People have been begging them for years to be honest with us. They look amazing. We just want to know… we're not asking to judge, we’re asking because we want to copy it.” — Claudia (32:46)

• On Sydney Sweeney’s acting choices:
  “It's like, sometimes it's okay to just have a lane.” — Claudia (40:07)
  “She needs a DiCaprio movie… she needs those roles.” — Ben (40:51)

• On Twilight vs. Batman Trilogy:
  “Not only is it incredible, it is the best acting, writing, cinematic…” — Claudia (44:09)
  “Sorry, Pattinson, that was not a good Batman… it's not your fault.” — Ben (44:55)

"Dear Toasters" Advice Segment (Principal Cases & Timestamps)

(53:11 – 62:15)

• 1. Potluck Kid’s Birthday Party Invite (53:11)
  Question: Is it tacky for a host to ask guests to bring food to a child's birthday?

  • Ben wants more context: “I’d love to understand what kind of year has she had?” (53:44)
  • Both agree: If the host is struggling, community support is sweet. If not, it's a strange move.
  • Claudia: “Do an audit of the social media… if they're living well and their kid is not, it's tough.” (55:16)

• 2. Niece’s Boy Secrets (56:00)
  Should an aunt keep secret her niece’s confessions about talking to boys?

  • Claudia and Ben go back and forth but agree: Mom needs to know, but aunt can’t be “ratted out.”
  • “Mom needs to know. But under the guise of being like, you can’t fucking rat me out because, one, we’re going to lose our information highway, and two, you’re going to make me look like a rat.” — Claudia (57:31)

• 3. Asking a Former Friends-With-Benefits for Sperm Donation (59:06)
  Is it nuts to ask a former FWB to provide sperm for embryo freezing?

  • Main advice: Only reach out if he’s single.
  • Ben: “If he’s single, what’s the worst… he could say no?” (59:53)
  • Claudia: “You can’t just text this… why don’t you ask him to dinner? You rekindle the friendship. Perhaps you get in one last quickie.” (60:50)

Timestamps for Key Segments

• 00:39 — Florida weather & snow in New York
• 02:25 — Feedback on Friday’s guest host episode
• 03:12 — Bert Kreischer “content mansion” story
• 05:19 — Claudia’s tooth saga & root canal story
• 11:56 — Ben’s tongue scraping journey
• 23:25 — Fast 5 stories begin (Hilary Duff’s tour)
• 27:42 — Kris Jenner’s party/Meghan Markle photo drama
• 31:03 — Kris’s facelift doctor & party costs
• 37:04 — Sydney Sweeney’s box office fail
• 41:54 — Robert Pattinson says he’d return to Twilight
• 53:11 — Dear Toasters advice segment begins

Tone and Banter

• Typical Oshry humor: unfiltered, sometimes raunchy (but always self-aware), brutally honest, quick-witted, and playful with running marital jokes and affectionate teasing.
• Ben fills in as a chaos agent, confidently delivering hot takes and dad jokes, often self-deprecating.

Summary Takeaways

• This episode is a quintessential Toast experience: real-life confessionals (from Claudia’s dentistry to bizarre gifting history), genuine relationship humor, and on-point celebrity commentary.
• The breadth of content spans from oral hygiene trends to celebrity surgery, with time for an impromptu Hilary Duff duet and thoughtful (if rowdy) listener advice.
• Highlights include Claudia’s “toothless wonder” saga, Hilary Duff acoustic hand-wringing, and the hilarious Twilight vs. Batman cinematic debate.

If you missed it, this episode is a balance of relatable lifestyle themes and sharp pop-culture coverage, all wrapped in the Oshry signature blend of warmth and wit.