The Toast – “Toastoween I Turned Pretty”

Date: October 31, 2025
Hosts: Claudia Oshry & Friends (no Jackie – on maternity leave)
Theme: A hilarious, high-energy Halloween special themed around the show The Summer I Turned Pretty, featuring costumes, playful improvisations, pop culture commentary, and the trademark “Fast Five” stories.

Episode Overview

This Halloween, Claudia and her co-hosts celebrate “Toastoween” by donning costumes of characters from The Summer I Turned Pretty, blending rollicking in-character banter with their signature pop culture takes. Despite Jackie’s absence (on maternity leave), the episode is packed with energy, inside jokes, and the Fast Five—covering the 2025 Word of the Year, celebrity relationships, TV drama, and a wild conversation about organ donation.

Key Discussion Points & Insights

1. Toastoween: In Costume as “The Summer I Turned Pretty”

• The crew dresses and roleplays as characters: Conrad, Jeremiah, Belly, mimicking their personalities and relationships with humorous improvisation.
• Memorable Quotes:
  • [00:28] Claudia: “It’s Conrad Fisher, and I’m here with my brother, who’s a little bitch.”
  • [00:43] Guest as Belly: “My name is Billy Conklin. Hoo. And I’m here with my boyfriend Conrad and Jeremiah, my two brother boyfriends…”
• Costume critiques and comparisons fly (“You look like Ellen with a mole”, “Margo, you look just like Jeremiah”), with witty commentary on wig choices and makeup ([08:04] “It’s Crawford. It’s like very good makeup. Isn’t that great mole?”).
• Ben, unfamiliar with the show, asks for explanations on characters and storylines, leading to playful, often inaccurate synopses ([12:03] “Let’s not introduce Stephen. It’s going to confuse him.”).

2. Inside Jokes and Running Gags

• Jackie’s absence is honored, with recurring references to her as “Laurel” or “Susannah” (the moms from the show) ([01:12] “We must honor our fallen sister. She is not here on her maternity leave.”).
• There are repeated jokes about personalities (“Bearded Belly”, “self-hating Jer”) and quirks of the characters.
• Claudia muses on “weird” book/show details like the nickname “Belly” ([06:05] “Her name is Isabelle, and her nickname is Belly, which is such a crazy part of the book and show like, that people don’t talk about.”).

3. Pop Culture Fast Five

1. 2025 Word of the Year: “67” ([16:46])

• Dictionary.com unveils “67” (from the Skrilla song lyric) as Word of the Year—but no one really knows why or what it means.
  • [16:53] “You’re kidding...I actually don’t know. I’ve been seeing ‘67’ everywhere and it’s the one trend I refuse to figure out.” – Margo
  • [18:02] “So, like, I’m feeling 67.”
  • [19:01] “Dictionary.com is solo brow.” – Claudia
• Hosts mock the ambiguity (“mid”, “ambiguous slang”), frustrated by meaningless viral terms.

2. Megan Thee Stallion & Klay Thompson Buy a House ([22:08])

• Discussion about Megan Thee Stallion and NBA star Klay Thompson’s new house—and who makes more money in sports.
  • Lively debate over which athletes (NBA, soccer, baseball) command the biggest salaries.
  • [24:22] “Back to the story. They bought a house together. Klay Thompson and Megan Thee Stallion. Now I want to know, Ben, who do you think has more money?”
  • [24:53] “No NBA players these days. The contracts are so—” – Ben

3. Dancing With the Stars: Drama Among the Pros ([27:33])

• Recap of recent drama: Max apologizing to Yon, and speculation about cast relationships.
  • [27:47] “Max is giving, like, actual stalker…”
  • [29:00] “There’s a lot more I want to say. I would like an opportunity to do it over coffee or any time you have to spare.”
  • Casting gossip, relationships formed (and broken) on the show, and harsh training.
  • [35:03] “Well, I saw a video of Max’s time on the show when he was training Hope Solo, and he shoved her and made her cry…”

4. Ashley Tisdale & Kenny Ortega High School Musical Reunion ([29:50])

• Surprised to spot Ashley Tisdale and Kenny Ortega at DWTS supporting Dylan Efron.
  • The group finds the reunion “weird” ([32:11] “It is very weird.”).
  • Discussion about cables/streaming problems for watching live TV.

5. Jesse Eisenberg Donates Kidney to a Stranger ([37:29])

• The hosts express awe and skepticism over Jesse Eisenberg’s planned altruistic organ donation.
  • [37:44] “Jesse Eisenberg is donating a kidney to a stranger, and he’s calling it a no-brainer.”
  • [38:36] Ben: “I just refuse to believe that if you donate your kidney, you’re fine afterwards.”
  • Engaging debate about who they’d donate kidneys to—family, best friends, hypothetical character choices ([39:30] “Like Belly, would you give Conrad or Jeremiah a kidney?”).

Notable Quotes & Exchanges

[00:28] Claudia (as Conrad): “It’s Conrad Fisher, and I’m here with my brother, who’s a little bitch.”
[07:24] Ben: “I just think I’m really a gorgeous woman.”
[08:17] Claudia: “I just like hate moles, my own included. And having to play someone, I’m being taken back to a very dark time.”
[16:53] Margo: “I’ve been seeing 67 everywhere and it’s like the one trend I refuse to like figure out what it is.”
[19:01] Claudia: “Dictionary.com is solo brow.”
[29:00] Max (via Claudia): “There’s a lot more I want to say. I would like an opportunity to do it over coffee or any time you have to spare.”
[38:36] Ben: “I just refuse to believe that if you donate your kidney, you’re fine afterwards.”
[39:30] Claudia (to Ben): “Like, Belly, would you give Conrad or Jeremiah a kidney?”
[40:02] Claudia: “Jeremiah, you are not the father.”

Funniest or Most Memorable Moments

• Banter About the Nickname “Belly” ([06:12]):
  “It’s the worst nickname you could ever have.” – Margo
  “But it’s the perfect nickname for you.” – Claudia

• In-Character Antics:
  [04:44] “I love you. I love you. No, like, it’s just, like, you know when, like, you don’t have to do anything. You just sit back and, like, it gets taken care of for you.” – Margo

• Debate Over Sports Contracts ([25:23]):
  “I think soccer is number one. I think NBA is number two.” – Ben
  “You guys, you’re sleeping on baseball.” – Claudia

• Jesse Eisenberg’s “No Brainer” Organ Donation ([37:44]):
  “He didn’t come on the Today show to say this. They were like, talking about a blood drive… ‘I’m donating my kidney in six weeks. I really am.’” – Claudia

• Character Choice Hypotheticals:
  [39:30] Claudia: “Like, Belly, would you give Conrad or Jeremiah a kidney?”
  [39:53] Ben: “I’ve decided to give my kidney to… Jeremiah.”
  [40:02] Claudia: “Jeremiah, you are not the father.”

• Unfiltered Costume Commentary ([08:08]):
  “It’s Crawford. It’s like very good makeup. Isn’t that great mole?” – Ben

• Cable & Streaming Struggles ([30:22]):
  “We need cable back. We can’t watch Nick’s games.” – Claudia

Important Segment Timestamps

• [00:28] – Host introductions, in-character
• [07:24] – Gender swapping and cross-dressing for Toastoween
• [12:03] – Explaining “The Summer I Turned Pretty” to Ben
• [16:46] – Fast Five: Word of the Year “67”
• [22:08] – Fast Five: Megan Thee Stallion & Klay Thompson buy a house
• [29:50] – Fast Five: Ashley Tisdale & Kenny Ortega reunion
• [37:29] – Fast Five: Jesse Eisenberg kidney donation
• [39:30] – Who would you donate a kidney to? (Character and personal hypotheticals)
• [41:01] – Funeral scene reenactment and more character play

Tone & Language

The episode bursts with unscripted, irreverent, and occasionally chaotic energy. The hosts riff freely—roasting each other, lampooning pop culture, and breaking the fourth wall—while retaining an affectionate tone toward the material and their friend Jackie. They balance silliness with sharp observations, making the Fast Five genuinely informative amid their Halloween mischief.

Summary

If you missed the episode, you’d have learned:

• The meaninglessness (and meme-worthiness) of “67” as the Word of the Year,
• The economics of superstar athlete couples,
• TV show relationship drama, both fictional (The Summer I Turned Pretty) and real (Dancing With the Stars),
• Some streaming woes in the “cable-cutter” era,
• And a surprisingly deep, silly, and philosophical roundtable about kidney donation—all while the hosts are decked out as Teen Beach drama characters, never breaking stride.

Don’t miss this one-of-a-kind Toastoween: costumes, laughs, and the pop culture run-down you need—delivered with the acerbic wit and camaraderie that defines The Toast.