Podcast Summary: Brooke and Jeffrey – Second Date Update: "Leave Wicky Alone"

Release Date: January 16, 2026
Host: iHeartPodcasts
Segment: Second Date Update

Episode Overview

This edition of "Second Date Update" dives into the unusual aftermath of a first date gone awry. Listener Ricky enlists the team’s help to uncover why Annette hasn’t called him back after their outing. What starts as a classic ghosting scenario quickly spirals into a hilarious but cringeworthy exploration of mismatched expectations, childlike wonder, and... public clapping at dinner. The episode’s main theme is unpacking the difference between harmless quirkiness and red-flag-level immaturity—and whether a “child at heart” approach to adulthood is ever dateable.

Key Discussion Points & Insights

1. How Ricky and Annette Met (03:39–04:09)

• Ricky shares he met Annette on a new dating app called "Can Do Better"
  • "You upload a picture of yourself... but what you do is you also draw a picture of the person you’re looking for." (E, 03:10–03:17)
  • The panel jokes about the app’s premise, stick-figure skill levels, and compatibility matching.
  • Ricky’s drawing: "It was green eyes and brown hair. And she had green eyes and brown hair." (E, 03:57–04:01)

2. The Mom Drop-Off Reveal (04:17–05:13)

• Ricky confesses his mom dropped him off for the date and later picked him up—because of unspecified "temporary" circumstances (later revealed as part of a larger lifestyle choice).
  • "She saw me get dropped off by my mom." (E, 04:32)
  • "She also yelled out after I got out of the car: ‘Good luck, sweetie!’" (E, 04:50)
• The hosts riff on how this could be played off, if at all:
  • “He could have pretended it was his Uber driver!” (D, 08:42)

3. Ricky’s Unusual Restaurant Behavior (05:34–06:47)

• Ricky admits he was likely overly enthusiastic at dinner since he rarely eats out: "They bring it out to you. I just kept complimenting the service and everything." (E, 05:40)
  • The team teases out his wide-eyed excitement and “childlike wonder,” likening it to “being at Disneyland” (D, 06:05).
  • Reflects on how the start and end of a date can overshadow the actual content.

4. Ricky’s Theories on the Ghosting (06:47–07:44)

• Ricky suspects the mom drop-off/ pick-up is the main dealbreaker.
  • "I just want to know why she’s not calling me back." (E, 06:47)
• Hosts point out bookending first date with “mom talk” isn’t ideal.

[CALL TO ANNETTE] The Reveal – Annette’s Perspective (09:48–12:00)

• Team calls Annette, who is clearly taken aback and reluctant to share.
  • "Why would I tell you any of this? I did not feel a connection." (H, 11:15)
• She surprises everyone:
  • The mom situation was “a little weird,” but NOT the main problem. (H, 11:49)
  • “There was a lot of clapping.” (H, 12:02)
    • For every course, water refill... “He’s a grown man on a date, y’all.” (H, 12:34)

Bombshell: Ricky Chooses to "Live Life as a Kid" (12:37–13:48)

• Annette claims Ricky openly told her at dinner that he “chooses to live his life as a kid.”
  • "He has a full time regular job, but he lives with his parents, and he’s kind of in denial about actually growing up. He just wants to like, shut things out and live as a kid, because it's more simple." (H, 13:00)
• “I sincerely believe he was wearing a pajama top.” (H, 13:43)

Live Confrontation: Ricky Explains Himself (14:10–17:10)

• Ricky is brought into the call. He stands by his approach, calling it “childlike wonder and excitement.”
  • "Everybody hates [being an adult]... and I have the opportunity to just not pay mortgage..." (E, 15:08)
  • Saving up for “big Lego sets” is both financial planning AND an example of his priorities (E, 15:31–15:38).
• Tension mounts over whether his lifestyle is quirky or off-puttingly immature.
• Ricky’s voice is called out for sounding childlike: “I like speaking that way. It just makes people expect less of me.” (E, 17:14–17:22)
• Annette is NOT swayed: "At this point, that would feel predatory." (H, 17:55)
• Ricky, feeling slighted, signs off: "I don't know what's wrong with you. I’m a man." (E, 18:01)

Memorable Quotes & Moments

• On Ricky’s excitement:
  "They bring it out to you. I just kept complimenting the service and everything." – Ricky (05:40)
• On the unique dating app:
  "You also draw a picture of the person you’re looking for." – Ricky (03:10)
• Annette on Ricky’s clapping:
  "For everything. Like, every course that came." – Annette (12:18)
• Annette’s breaking point:
  "He chooses to live his life as a kid... because it's more simple." – Annette (13:00)
• Ricky’s defense:
  "Everybody hates [being an adult]... I have the opportunity to just not pay mortgage and just..." – Ricky (15:08)
• On money priorities:
  "I save money for things that I like, you know, like big Lego sets." – Ricky (15:31)
• Annette's final answer:
  "Absolutely not… At this point, that would feel predatory." – Annette (17:44, 17:55)

Timestamps for Key Segments

• How They Met and “Can Do Better” App: 03:10–04:09
• Mom Drop-Off Story: 04:17–05:13
• Ricky’s Restaurant Enthusiasm: 05:34–06:47
• Ricky Suspects the Ghosting Cause: 06:47–07:44
• Annette’s Side – The Real Issue: 12:00–13:43
• Ricky’s Explanation and Childlike Persona: 14:10–17:10
• Annette’s Final Rejection: 17:44–17:55

Tone & Overall Experience

The exchange is light, humorous, and cringeworthy in classic "Brooke and Jeffrey" fashion, striking a balance between empathy and playful mockery. The hosts are supportive yet candid, and the guest’s quirks make for standout podcast entertainment, especially as the real reason for Annette’s ghosting comes to light. The team uses their signature banter, with Brooke trying to mediate, Jeffrey playing devil’s advocate, and the rest of the crew riffing on Ricky’s “childlike” lifestyle and its broader implications for modern dating.

Concluding Thoughts

The episode delivers high entertainment as promised—shedding light on why second dates sometimes don’t happen. Ricky’s story becomes both a cautionary tale and a comedic highlight for listeners. The hosts wrap up by declaring Ricky a “hero to all men” for making everyone else look more dateable by comparison and encourage listeners to celebrate their own (hopefully grown-up) dating wins.