Podcast Title: Brooke and Jeffrey: Second Date Update
Episode: Classic: Due the Math
Release Date: January 11, 2025
Host/Author: iHeartPodcasts

Introduction to the Episode

In the "Classic: Due the Math" episode of Brooke and Jeffrey: Second Date Update, hosts Kat Dennings and Jeffrey delve into the complexities of modern dating through the lens of mathematical compatibility. The episode spotlights Justine, a listener who recently experienced a unique first date that ended unexpectedly, leading her to seek a "Second Date" with the help of the show.

Justine's Story: The Dating Math

[02:33 – 05:01]

The episode begins with Justine sharing her experience of using an online test designed to calculate compatibility based on personal preferences. As Justine explains, "It's like this online test. You put in all the stuff that you care about, like your preferences and whatever for, like, finding a partner, and it's supposed to come back with, like, the percentage of men on dating apps who, like, fit those preferences." Despite her seemingly reasonable criteria—such as valuing a partner with a job and independence—the test returned a disheartening result: less than 1% of men matched her preferences.

The Meeting with James

[04:42 – 06:18]

Against the bleak statistics, Justine recounts meeting James serendipitously at a coffee shop. Instead of through a dating app, James approached her with an unconventional "boyfriend application" line: "Are you accepting applications?" Initially perplexed, Justine was amused when James produced a "dating resume," listing his interests and experiences. She shares, "He legitimately, like, pulled out a piece of paper."

James extended the interaction by offering to Venmo her for the coffee she had already purchased, demonstrating his considerate nature. This creative approach set the stage for what seemed like a promising connection.

The Interview Approach

[06:18 – 07:10]

Justine decided to take the dating interview seriously, leveraging her professional experience to ask James thoughtful questions, such as, "What's one thing you don't want me to know about you?" James responded candidly, revealing a personal vulnerability: "I cry when I watch the Matrix because I'm scared about the future." This honesty impressed Justine, who found his response both funny and genuine.

Ghosting After the First Date

[07:49 – 08:18]

Despite the positive interaction, Justine notes that James never followed up after their initial meeting. She mentions, "he never called me again," even after she jokingly suggested setting up a second interview. Attempts to reconnect through text were met with silence, leaving Justine both puzzled and disappointed.

The Second Date Update: Inviting James

[11:07 – 16:54]

Determined to uncover the reasons behind James' disappearance, Kat and Jeffrey decide to bring James onto the show for a "Second Date Update." They reach out and successfully connect with him, initiating a live conversation.

Interview with James: His Dating Resume Approach

[11:21 – 17:45]

During the interview, James explains that his practice of using dating resumes is a well-honed strategy aimed at making meaningful connections. He admits to having approached numerous women with this method: "I've done that a good amount."

James shares anecdotes of diverse responses, including interactions with an "extreme couponer" and a woman obsessed with alien abductions, highlighting the varied reactions his approach elicits.

When discussing his interaction with Justine, James reveals that her quick wit and out-of-the-box thinking "freaked him out." He admits, "I didn't know how to respond," indicating that Justine's sharpness caught him off guard. This encounter marked a turning point for James, making him consider the possibility of a genuine connection beyond his usual tactics.

Insights and Conclusion

[17:46 – 18:28]

Kat and Jeffrey analyze James' approach, questioning its efficacy and long-term viability. They humorously speculate about James potentially applying to "multiple boyfriend positions" across the city due to the scalability of his method.

The episode concludes with an invitation for James and Justine to embark on a "second interview," transitioning their interaction from a staged date to a more authentic connection. This move underscores the show's commitment to not only entertain but also facilitate real-life relationship developments.

Notable Quotes with Timestamps

• Justine on the Perfomance of the Dating Math Test:
  "It's supposed to come back with, like, the percentage of men on dating apps who, like, fit those preferences."
  [03:47]

• James Explaining His Approach:
  "I've done that a good amount."
  [12:16]

• Justine on the Outcome of Their Interaction:
  "He never called me again."
  [07:49]

• James Reflecting on His Interaction with Justine:
  "I never take this thing seriously. It's just sort of a gimmick."
  [13:44]

• Kat on James' Challenge:
  "Can you try to say it a little more assertive?"
  [16:31]

Final Thoughts

"Classic: Due the Math" offers a humorous yet insightful exploration of the intersection between modern dating strategies and personal connections. Through Justine and James' stories, the episode highlights the unpredictability of human relationships and the challenges of finding genuine compatibility in an increasingly algorithm-driven dating landscape. Kat and Jeffrey effectively balance humor with heartfelt moments, making this episode both entertaining and relatable for listeners navigating their own dating experiences.