Brooke and Jeffrey: Second Date Update – "I Got Cheesecaked"

Release Date: August 11, 2025
Hosts: Brooke and Jeffrey
Podcast Platform: iHeartPodcasts

Introduction to the Second Date Update Segment (03:39 - 04:05)

Brooke and Jeffrey dive into the main segment of the episode, introducing the second date saga of their listener, Corey. Corey reached out to the show after experiencing a less-than-ideal first date with a woman named Allison, prompting him to seek advice on securing a second date.

Corey's First Date Experience (04:06 - 08:10)

Corey shares his ambitious effort to secure a second date by flying out to meet Allison, demonstrating significant commitment and enthusiasm.

• Corey’s Commitment: Corey chose to fly out for an entire weekend to meet Allison, highlighting his dedication.
  "I had a free weekend. I'm like, I'm free next weekend. What if I fly up there?" (04:18)

• Meeting at a Restaurant: The couple met at a chain restaurant where the conversation flowed smoothly, characterized by laughter and a playful guessing game about the occupations of people around them.

  • Notable Quote:
    "We were playing this game where it was like, let's look at the people around us and try to guess what job that they would have." (06:47)

• Dessert at Cheesecake Factory: Post-dinner, they decided to grab dessert at the Cheesecake Factory, opting to take it to go and enjoy it at a nearby park.

  • Pricing Surprise: Corey was taken aback by the high prices, noting,
    "I was floored by the prices, actually, at Cheesecake Factory, to be honest." (07:46)

• Plans for the Next Day: Corey intended to spend more time with Allison by potentially meeting for brunch before his departure, showing his desire to deepen the connection.

The Disappointing Follow-Up (08:10 - 09:35)

Corey reaches out the next day, only to receive disappointing news from Allison.

• Allison’s Excuse: She informs Corey that she cannot hang out as her grandma has an event, leading Corey to question whether the excuse was genuine or a polite way to decline further interaction.

  • Corey’s Confusion:
    "She didn't say no, but she was just like, sorry, I have this. My grandma has this thing and I can't hang out today." (08:23)

• Hosts’ Perspective: Brooke and Jeffrey discuss the possibility that committing to a long-distance relationship from the outset may have been premature for Corey.

  • Jeffrey's Take:
    "It's hard for long term relationships to be long distance, let alone starting a brand new one." (11:13)

Confrontation with Allison (11:30 - 19:37)

In an unexpected turn, Brooke and Jeffrey decide to call Allison live on air to seek clarity on Corey’s behalf.

• Initial Contact:
  "Hey, is this Allison?" (11:30)

• Allison’s Reaction: Initially defensive, Allison responds with anger, revealing the true reasons behind her lack of communication.

  • Allison’s Outburst:
    "I was like, wow, this guy's a loser." (16:11)
    "I want you to never talk to me. That's why you didn't hear from me." (18:23)

• Corey’s Missteps Exposed:

  • Offensive Comments: Corey had made insensitive remarks about Allison’s nose ring, implying she had "daddy issues," which Allison found offensive. "Because I'm trying to understand how many daddy issues you have." (13:07)

  • Financial Misunderstanding: Corey awkwardly asked Allison to pay for dessert, which came off as inconsiderate given he was the one who flew out. "He asked me to get my card out to pay? You suggested getting the cheesecake." (15:10)

• Outcome: The confrontation leaves no room for reconciliation, confirming that Corey did not secure a second date.

  • Host’s Conclusion:
    "It's not going to be another date with Allison. It's a no from her, obviously." (19:15)

Hosts’ Analysis and Conclusions (19:37 - 22:34)

Brooke and Jeffrey dissect the events leading to the failed second date, offering insights and reflections.

• Corey’s Lack of Self-Awareness: The hosts highlight Corey's inability to recognize his own flaws and the impact of his actions on Allison.

  • Jeffrey’s Insight:
    "Corey, it's not going to be another date with Allison. It's a no from her, obviously." (19:28)

• Educational Takeaways:

  • Effective Communication: Emphasizing the importance of clear and respectful communication in dating.
  • Sensitivity to Others’ Feelings: Advising listeners to be mindful of their remarks and considerate of their date’s perspectives.

• Final Thoughts: Corey’s experience serves as a cautionary tale about the pitfalls of jumping into long-distance dating without establishing a strong foundation and understanding mutual respect.

Closing Remarks and Lessons Learned (22:34 - 23:18)

The episode wraps up with a summary of the key lessons from Corey’s dating misadventures.

• Learning Opportunity:
  "Hopefully he takes it as a learning experience for what not to do and what not to say and what body piercings not to draw dumb conclusions from." (22:34)

• Final Advice: The hosts encourage listeners facing similar situations to seek support and remain resilient in their dating journeys.

Transcript Excerpts: Notable Quotes

1. Corey on Flying Out:
   "What if I fly up there?" (05:37)

2. Corey on Dessert Plans:
   "Let's get some dessert there and take it to the park." (07:32)

3. Allison’s Confrontation:
   "I want you to never talk to me." (18:23)

4. Hosts on Corey's Future Dating:
   "You're back onto the dating app. Just where you want to be." (19:29)

Key Takeaways

• Commitment vs. Compatibility: Showing dedication through significant efforts like long-distance visits is commendable, but compatibility remains paramount.

• Communication is Crucial: Missteps in conversation, such as insensitive jokes or financial misunderstandings, can derail budding relationships.

• Respect and Sensitivity: Understanding and respecting a partner’s feelings and perspectives are essential for building trust and rapport.

• Learning from Mistakes: Every dating experience, positive or negative, offers valuable lessons for personal growth and future relationships.

Conclusion:
In this episode of "Brooke and Jeffrey: Second Date Update," listeners are provided with an honest and entertaining look into the complexities of modern dating. Corey's story underscores the importance of self-awareness, effective communication, and mutual respect in fostering meaningful connections. Brooke and Jeffrey adeptly navigate the nuances of Corey's misadventures, offering both humor and heartfelt advice to their audience.