Podcast Summary: The Toast
Episode: All Things Trout with Olivia Oshry
Host: Dear Media
Release Date: June 13, 2025
Introduction & Co-Hosting with Olivia "Trout" Oshry
In this special episode of The Toast, hosts Jackson Claude and his sister Olivia Oshry, affectionately known as "Trout," come together to celebrate "Happy Trout Day." The dynamic duo engages in lighthearted banter, setting an engaging and familial tone for the episode.
Notable Quote:
Jackson Claude [00:24]: "Welcome back to The Toast. Happy Friday. Happy Trout Day. I am joined today by my big sister, Olivia, AKA Trout."
Olivia Oshry: Behind the Trout
Olivia provides listeners with an in-depth look into her life, highlighting her passion for cooking, gardening, and her extensive 15-year career in marketing. She emphasizes her love for brands, great advertising, and her role within the family.
Notable Quote:
Olivia Oshry [02:38]: "I share a lot about, like, food, things that I love to eat, brands that I love. I have been in marketing for 15 years, so, like, I'm a very brand-centric person."
Merchandise & Brand Collaborations: The Cardigan Conversation
A significant portion of the episode delves into Olivia's enthusiasm for "The Toast" cardigan, a beloved piece of merchandise. Olivia passionately advocates for its return, suggesting a collaboration that would feature a trout-themed design, aligning with the show's branding.
Notable Quotes:
Olivia Oshry [06:02]: "I have a collab idea, and I'm just putting it out there. Like, I'm shooting my shot. Cause I'm here."
Jackson Claude [07:29]: "No, see, and that's amazing."
The discussion underscores the importance of merchandise in fostering community and brand loyalty among listeners.
Main Stories: Engaging Discussions and Hot Topics
1. Love Island Recap & Florida's Allure
The hosts transition into their first story, focusing on recent events in Love Island. They discuss the pairing of Taylor Swift and Travis Kelce at the Stanley Cup Final in Sunrise, Florida, highlighting the state's vibrant lifestyle and its impact on both celebrities and local sports teams.
Notable Quote:
Olivia Oshry [17:25]: "I was in New York this week for a business trip, and everyone's like, oh, what are you up to? And I'M like, well you know, like I live in Florida now."
The conversation emphasizes Florida's appeal, particularly for families and sports enthusiasts, and speculates on the longevity of celebrity stays in the state.
2. Sabrina Carpenter's Album Cover Controversy
The episode addresses the backlash surrounding Sabrina Carpenter's new album cover for "Man's Best Friend." Critics have labeled the imagery as misogynistic and degrading towards women, sparking discussions about the responsibilities of artists in shaping public perception.
Notable Quotes:
Jackson Claude [23:39]: "The image doesn't look like an album cover. I saw it so many times before I realized it's an album cover."
Olivia Oshry [25:47]: "I think I really agree... it's just that visual sort of recognition and imagery that I think generally speaking, we could do better."
The hosts express their disapproval of the cover's quality and message, advocating for more thoughtful and empowering representations in the music industry.
3. The Traitor Season 4 Casting Rumors
Rumors abound regarding the casting of Season 4 of The Traitor, with sixteen stars tentatively named, including reality TV personalities like Donna Kelsey and Maura Higgins from Love Island. The hosts analyze the potential dynamics these contestants could bring to the show.
Notable Quotes:
Jackson Claude [28:54]: "Mama Kelsey's got agents and managers and, like, and this is doing it right for her."
Olivia Oshry [30:23]: "I think there's always people that come in with an agenda to be, like, super aggressive and, like, backstabbing and, like, I just, like, that's not what she's gonna come. That's not her energy."
The discussion highlights the strategic nature of reality TV casting and anticipates engaging interactions among the diverse group of contestants.
4. Grammys 2026: New Categories and Representation
The hosts explore the Recording Academy's announced changes for the 2026 Grammy Awards, introducing two new categories: Best Traditional Country Album and Best Album Cover. They discuss the implications for country artists and the broader music community.
Notable Quotes:
Jackson Claude [34:16]: "Best Album Cover is so fucking weird and stupid to me."
Olivia Oshry [36:55]: "The kids today could use a little bit more wholesomeness."
While supportive of increased country music representation, the hosts express confusion and skepticism about the necessity and clarity of the new Best Album Cover category.
Dear Toasters: Listener Advice Segment
In this week's Dear Toasters, Jackson and Olivia address listener-submitted questions, offering heartfelt and practical advice.
Advice 1: Navigating Parental Titles
A mother expresses concern over her son transitioning from "Mom" to "Mama," causing friction with her husband.
Advice Highlights:
- Olivia reassures the mother, emphasizing the sweetness of the son's choice.
- Jackson humorously suggests the husband might be feeling left out.
Notable Quotes:
Olivia Oshry [51:40]: "Let your kids be expressive in the names they want to call you."
Jackson Claude [52:11]: "Your son isn't doing anything wrong."
Advice 2: Handling a Brother-in-Law's Infidelity
A listener seeks guidance on managing a strained relationship with her brother-in-law's new girlfriend, who has been unfaithful.
Advice Highlights:
- Olivia encourages honesty and setting boundaries.
- Jackson advises deferring responsibility to the husband and maintaining distance without fostering animosity.
Notable Quotes:
Olivia Oshry [55:15]: "She deserves to know."
Jackson Claude [56:42]: "Punt the ball."
Advice 3: Deciding on Last Names After Marriage
A married woman grapples with whether to change her last name, considering her close ties to her own family and her husband's distant family.
Advice Highlights:
- Olivia shares her personal approach of using a hybrid name for professional and personal contexts.
- Jackson discusses the traditional expectations and modern alternatives, emphasizing personal choice over societal norms.
Notable Quotes:
Olivia Oshry [63:00]: "I'm Mrs. Shapiro, Mr. Shapiro. It's just easier for the kids to have the same last name."
Jackson Claude [64:42]: "It's not crazy. More modern women aren't changing their names for a number of reasons."
Conclusion: Embracing Authenticity and Community
As the episode wraps up, Jackson and Olivia reflect on the importance of authenticity in personal branding and the value of community support. Olivia highlights her engagement with listeners through social media and Patreon, emphasizing the intimate connections fostered beyond the podcast.
Notable Quote:
Olivia Oshry [66:45]: "I share bits and bobs of my life and my food and my cooking and my life and my whatnot."
The hosts leave listeners with a sense of camaraderie and encouragement to embrace their unique identities while navigating personal and professional challenges.
This episode of The Toast offers a blend of personal insights, engaging discussions on current pop culture topics, and meaningful advice segments, all enriched by the warm and relatable interactions between Jackson Claude and Olivia Oshry. Whether you're a long-time listener or tuning in for the first time, this episode provides valuable perspectives and heartfelt conversations that resonate with a wide audience.