Call It What It Is: Episode Summary with Jenna Ashkowitz, Kevin McHale, Jessica Capshaw, and Camille Ludington
Release Date: May 5, 2025
In this engaging episode of "Call It What It Is", hosted by Jenna Ashkowitz and Kevin McHale, alongside special guests Jessica Capshaw and Camille Ludington, the crew delves deep into the complexities of modern friendships and romantic relationships. The episode is rich with insightful discussions, personal anecdotes, and practical advice, making it a must-listen for anyone navigating the tumultuous waters of dating and maintaining meaningful connections.
1. Introduction and Welcoming Guest Jenna Ashkowitz (02:24 – 03:39)
The episode kicks off with a warm welcome to Jenna Ashkowitz, setting the stage for an in-depth conversation. Jessica Capshaw expresses admiration for Jenna's ability to resonate with her audience, highlighting Jenna's authenticity and intelligence.
Jessica Capshaw [03:07]: "Whenever someone comes around that's smart and feels like I can trust her, you get a new take on it. That's how I remember coming to know who you are."
2. Unveiling the Box Dating Theory (08:24 – 14:08)
Jenna introduces her Box Dating Theory, a framework that categorizes how individuals perceive potential romantic partners during first encounters. According to Jenna, when a man meets a woman in a romantic setting—be it a date, app, or setup—he subconsciously sorts her into one of three categories:
- Wants to Date Her
- Wants to Hook Up with Her
- Doesn't Want Anything to Do with Her
Jenna Ashkowitz [08:37]: "Box theory is my theory that when a guy meets a girl in a romantic setting... he puts her into one of three boxes: wants to date her, wants to hook up with her, doesn't want anything to do with her."
Jenna emphasizes that these categories are rigid and often irreversible, creating confusion when expectations between the Date Box and Hookup Box clash.
Jenna Ashkowitz [09:20]: "You can't move from box to box. This is what really trips people up because... I've been in the hookup box."
3. The Dynamics of Dating in Los Angeles vs. New York (14:11 – 16:20)
The conversation shifts to the contrasting dating landscapes of Los Angeles and New York City. Jenna articulates the challenges unique to LA, such as geographic dispersion and a culture rife with flakiness, making spontaneous meetups difficult.
Jenna Ashkowitz [14:17]: "LA has a lot of flakiness... It's so touch and go on whether there's actually going to be people out, people just in their homes more."
Conversely, New York City offers a more conducive environment for dating, where commitments to meeting up are usually honored, akin to regular social activities like going to the gym.
Jenna Ashkowitz [14:35]: "In New York, you can go on a date... People will follow through."
4. Navigating Commitment and the Paradox of Choice (16:28 – 17:22)
Jenna discusses the current aversion to commitment prevalent among both men and women, attributing it to the Paradox of Choice—the overwhelming abundance of options facilitated by dating apps.
Jenna Ashkowitz [17:22]: "There's infinity hot people... Women are staying single longer... There's a record number of women over 30 who are single and unmarried."
This societal shift leads to higher standards and longer periods of being single, as individuals become more selective, often influenced by the endless swiping culture.
5. Introducing Jenna's Upcoming Book: "Hotter in the Hamptons" (23:00 – 26:28)
Jenna shares her excitement about writing a book titled "Hotter in the Hamptons", inspired by her transformative experiences during a weekend getaway. Initially dismissive of the Hamptons' reputation, she found joy in hosting her friends, leading to a fresh perspective on the area.
Jenna Ashkowitz [25:00]: "We're going to have a new badass heroine... Slutty White Lotus without the death."
The book aims to explore various "rich mom" locales, blending humor and sharp social commentary, drawing comparisons to popular shows like "White Lotus".
6. Listener Q&A: Tackling Real Relationship Dilemmas (31:11 – 47:45)
The heart of the episode features a Q&A session, where Jenna and the hosts address pressing relationship questions from their audience:
-
When to Give Up on a Relationship (31:11 – 32:52):
Jenna advises recognizing when there's no viable path forward in a relationship, emphasizing the importance of envisioning a future together.
Jenna Ashkowitz [31:20]: "Another trick is if you can't imagine doing the next thing with them... that's a good barometer for if there's a future."
-
Moving In Together (44:19 – 46:19):
The discussion centers on the right timing to propose cohabitation, advocating for honesty and mutual readiness without resorting to ultimatums.
Jenna Ashkowitz [44:50]: "I don't think it can hurt... Like if you're with the right person, it won't matter."
-
Overcoming Trust Issues (47:44 – 48:19):
Jenna emphasizes the therapeutic benefits of understanding and processing past betrayals to rebuild trust.
Jenna Ashkowitz [47:45]: "I'm a big therapy advocate... it can really help you work through why it was so hurtful."
-
Restarting Dating at 57 (41:57 – 43:12):
Offering encouragement, Jenna promotes viewing it as an exciting new chapter and recommends dating apps tailored for older demographics.
Jenna Ashkowitz [42:03]: "View it as an exciting new chapter... there's so many different eras that we all have."
Throughout the Q&A, the hosts and Jenna provide relatable and actionable advice, grounded in personal experiences and psychological insights.
7. The Power of Self-Awareness and Authenticity (39:32 – 39:45)
Jessica Capshaw and Jenna highlight the significance of maintaining self-awareness and setting personal boundaries, especially in an era dominated by digital interactions.
Jenna Ashkowitz [39:45]: "Pick your non-negotiables... Those are the things that really matter to you."
8. Closing Remarks and Future Endeavors (48:13 – End)
As the episode wraps up, the hosts express their gratitude to Jenna, applauding her insights and looking forward to her upcoming projects. The camaraderie among the hosts and guests underscores the episode's central theme of support and authentic connection.
Jessica Capshaw [48:22]: "Appreciate it. Thanks so much. I'll see you guys."
Notable Quotes with Timestamps
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Jenna Ashkowitz on Box Dating Theory:
"Box theory is my theory that when a guy meets a girl in a romantic setting... he puts her into one of three boxes."
[08:37] -
Jenna on the Challenges of LA Dating:
"LA has a lot of flakiness... It's so touch and go on whether there's actually going to be people out."
[14:35] -
Jenna Encouraging Therapy for Trust Issues:
"I'm a big therapy advocate... it can really help you work through why it was so hurtful."
[47:45] -
Jenna on Restarting Dating:
"View it as an exciting new chapter... there's so many different eras that we all have."
[42:03]
Conclusion
This episode of "Call It What It Is" offers a blend of personal stories, theoretical frameworks, and practical advice, all aimed at demystifying the modern dating landscape. Jenna Ashkowitz's Box Dating Theory provides a fresh lens through which to view romantic interactions, while discussions about the varying dynamics of cities like LA and NYC add depth to the conversation. The Q&A segment serves as a valuable resource for listeners grappling with their own relationship challenges, reinforcing the podcast's commitment to fostering genuine connections and personal growth.
Whether you're navigating the complexities of dating, striving to maintain meaningful friendships, or seeking insights into your own relationship patterns, this episode delivers thoughtful and actionable guidance, all wrapped in the hosts' signature wit and warmth.