The Toast – "The Season of Truth"

Hosts: Jackie Oshry & Claudia Oshry
Date: January 5, 2026
Episode: First Episode of 2026, Season 9 Premiere

Overview

In this energetic and candid season nine premiere, Jackie and Claudia reunite after maternity leave and the holidays for the first episode of 2026. Their central theme: embracing "truth"—personally, professionally, and culturally—for the year ahead. They reflect on major life updates, set intentions for the new season, and deliver the top pop culture stories in their signature “Fast Five” style, unpacking viral celebrity moments and personal anecdotes with honesty, wit, and irreverence.

Key Topics & Insights

1. New Year, New Season, New Intentions

[00:32–08:34]

• Jackie Returns from Maternity Leave:
  Jackie opens up about her slower, more intentional return, rejecting the pressure to "bounce back." She emphasizes honoring "two truths": returning to work but still being in the "newborn bubble" (02:06).

  “In the past, when I've come back from maternity leave, it's like, back, bounce back. And I feel like this time I'm putting a lot less pressure on myself.” - Jackie [02:06]

• Personal Growth & Shifting Dynamics:
  The sisters discuss living separately in Florida, enjoying personal space after years of cohabitation around their growing families and careers (03:46–04:22).

• Intentions for Season Nine:
  Both vow to bring greater authenticity and "cold hard truth" to the show, inspired by feeling less filtered behind sunglasses or audio-only episodes (07:18–08:50).

  “I want to lead in this season with authenticity… Cold hard truth.” – Jackie [07:24]

  “My goal here is to bring that [glasses energy of honesty] without the glasses.” – Claudia [07:46]

2. Navigating Life Changes

[04:38–06:28]

• Body Image, Ozempic, and Motherhood:
  Claudia talks about starting Zepbound (weight-loss medication), shares her progress ("lost six pounds"), and acknowledges the tension between weight loss and breastfeeding (04:42–05:54).

  “It's the dichotomy of women. In order to breastfeed adequately, you need to be in a calorie surplus. In order to lose weight, you need to be in a calorie deficit. They're butting heads.” – Jackie [05:35]

• Comfort in Studio Setup:
  They both appreciate shooting "chest up" in studio, joking about postpartum fashion and camera angles (06:33–06:52).

3. Embracing “Truth” as a Cultural Need

[13:42–14:15]

• Jackie and Claudia reflect on the "truthful season" they're entering, not just personally, but as something needed in the culture and among their generation.

• They resolve to be more direct and less veiled, even as the reality of having a public platform sometimes causes hesitation (08:50–09:58).

  “Having this great big platform is both a blessing and a curse and one that we try to walk as gracefully as one can.” – Claudia [10:23]

4. Celebrity & Pop Culture – The Fast Five Stories

Key stories, hot takes, and notable moments from pop culture
[22:07–44:08]

Story 1: Alex Earl & Tom Brady's Saint Bart’s Moment

[22:11–30:08]

• Alex Earl is spotted getting close to Tom Brady in Saint Bart’s, stirring debate about age, fame, and single-girl fantasy.

• Claudia’s dual perspective: Tom Brady’s behavior is “disgusting” but “she had to do it” as a rising it-girl [23:59–24:12].

  “Tom Brady, like, you're literally disgusting. Like, that could be your daughter… Alex Earle—Queen. Yes. I have two different perspectives based on who I'm talking about.” – Claudia [23:59]

• They agree Alex Earl isn’t likely to date Tom—and don’t “ship” the couple—but this moment marks her ascent to A-list status.

Story 2: Timothée Chalamet & Kylie Jenner

[30:08–36:41]

• Timothée's Critics Choice Awards speech calls Kylie his “partner of three years” and thanks her for their “foundation” [32:14–32:30].

  “I would like to say thank you to my partner of three years. Thank you for our foundation. I love you. I couldn’t do this without you.” – Timothée (as quoted by Jackie) [32:14]

• The hosts analyze his use of “partner” (not girlfriend), speculating on seriousness—marriage? babies?—and compare the buzz to “Britney and Justin” red carpets.

  “Partner sounds great. The relationship sound more serious. And him using the word partner… is crazy.” – Claudia [33:00]

Story 3: Kelsey Ballerini & Chase Stokes' Rekindled Romance

[37:46–44:08]

• After cheating rumors and messy Instagram pleas, Kelsey Ballerini and Chase Stokes are publicly back together.

• They dissect the "year of the heart," with Jackie skeptical of Chase's ability to change (“he’s a big cheater”) and both debating second chances in love.

  “I believe people can change. I'm big into chances… but I don't think that's something you should accept.” – Jackie [41:19]

• They discuss the double-edged sword of setting “high bar” expectations in music and real life, and the exhaustion of fan backlash.

Story 4: Zach Bryan Marries Samantha Leonard (Amidst Abuse Allegations)

[49:57–54:57]

• Zach Bryan surprises fans with a wedding in Spain, but the internet is shocked by his caption—“Tougher than the rest”—which appears to allude to his exes, including public abuse allegations from Brianna Chickenfry.

• Jackie and Claudia are unequivocal: referencing exes and a history of abuse in your wedding post is toxic and disturbing.

  “Making your first photo with your wife about your exes is such a toxic thing to do… When the rest of your exes have left you because you have been so abusive towards them, it makes the caption even crazier.” – Claudia [51:11]

• Brianna’s ambiguous TikTok reaction and the complexity of public healing are discussed, with a plea for more “primary sources” in 2026 [54:02].

Story 5: Joe Jonas Dating Model Tatiana Gabriella

[56:12–58:14]

• Joe Jonas is publicly coupled up again post-Sophie Turner, but the hosts aren’t feeling threatened.
• Riffing on celebrity partnerships, nicknames, and pop culture trivia (including Dakota Johnson, role model, and Emma Chamberlain).

5. Behind the Scenes: Personal Moments & Podcasting Realness

[43:43–61:14]

• Life After Breastfeeding: Claudia shares regaining her vitality after weaning, crediting Jackie for advice and reflecting on the trade-offs of motherhood [12:08–12:34].

  “Life begins when you stop breastfeeding... I am doing the best that I've been in, honestly, two years.” – Claudia [12:08]

• Podcast Milestones and Memories: Reflecting on nine seasons, anniversaries, and the changing landscape of their show (“We’ve actually been podcasting for 10 years. We don’t get enough credit for that.” – Claudia [14:53]).

Notable Quotes & Memorable Moments

• On Truth as a Theme:
  “We’re kind of in our truthful season.” – Jackie [13:44]

• On the Challenge of Public Commentary:
  “Having this great big platform is both a blessing and a curse…” – Claudia [10:23]

• On Motherhood & Identity:
  “Reading is something I’ve lost in motherhood… I have time, I just don’t have the will.” – Claudia [11:43]

• On Outgrowing the Internet:
  “Sometimes the public perception of your relationship cannot penetrate your relationship because you are so removed from the Internet—Kylie and Timothy. Right? But Chase and Kelsey? They know.” – Jackie [43:05]

• On Alex Earl’s Ascendancy:
  “This solidifies Alex as a true A-list celebrity.” – Claudia [26:12]

• On Pop Culture Fandom:
  “When I saw Kylie and Timothy, and I heard the speech, like, giddy. Straight up giddy. Loved. I love love.” – Claudia [36:14]

Timestamps for Important Segments

• Jackie Returns, Season Nine Vibes: [00:32–02:52]
• Setting Intentions for the Year & Season: [07:15–08:50]
• Discussion: The Truthful Era: [13:42–14:15]
• Alex Earl & Tom Brady Story: [22:11–30:08]
• Timothée Chalamet & Kylie Jenner Couple Dissection: [30:08–36:41]
• Kelsey Ballerini & Chase Stokes Relationship Drama: [37:46–44:08]
• Zach Bryan’s Wedding, Scandal Fallout: [49:57–54:57]
• Joe Jonas’ New Romance and Celebrity Digressions: [56:12–58:14]
• Motherhood Wisdom & Personal Reflections: [11:43–12:08]

Takeaways

• Season 9 is about authenticity and cold, hard truth—as individuals and as pop culture commentators.
• Motherhood, partnership, and personal goals are foregrounded in the hosts’ reflections and humor.
• Celebrity stories serve as a launching pad for candid takes on relationships, fame, and living online.
• Jackie and Claudia’s chemistry, honesty, and playful banter continue to define the show’s tone in 2026.

Tagline for the Year:
The Year of Truth