Brooke and Jeffrey: Second Date Update

Episode: Second Date Update: There's A Chili In The Air
Date: October 1, 2025
Network: iHeartPodcasts

Episode Overview

This episode of Second Date Update centers around Dorman, who seeks help after being ghosted by Yolanda following a unique chili-themed first date. As always, the hosts—Brooke, Jeffrey, Alexis, and Lauren—bring humor, empathy, and teasing to unravel why Yolanda hasn’t responded, and attempt to broker a second date, delivering classic awkwardness and laughter along the way.

Key Discussion Points & Insights

Setting the Scene: Dorman Reaches Out

• Dorman’s Situation: Dorman emails the show feeling "desperate," admitting he's tried every other avenue to get in touch with Yolanda, who isn’t returning his messages.

  "Desperation is what made our listener Email us for help today. Not saying he's desperate, but you know what it feels like..." (Brooke, 04:40)

• Dorman's Connection with Yolanda:

  • Met online; found her "intentional" and "playful"
  • Appreciated her effort in her dating profile, noting a witty Harry Potter tattoo reference

  “She seemed really intentional and playful…" (Dorman, 05:40)

The Notorious First Date

Why Chili?

• Dorman chose a local spot “world-famous for their chili,” hoping the food adventure would be a novel bonding experience.

  "I picked this spot. It's, like, really known for their chili...world famous." (Dorman, 07:01)

Date Conversations

• Dorman recounts being nervous and rambling, including:
  • Discussing his close relationship with his mom (she still packs his lunch every Friday)

  "There's a tradition from years ago...every Friday...I go to my mom's place to see her, and she always, like, packs my lunch for me." (Dorman, 08:14)

The Chili Backfire

• The physical repercussions of the chili cut the date short; Dorman needed to rush home, driving Yolanda home in obvious distress.

  “I didn’t think the chili thing through. I was like, I gotta hit the restroom.” (Dorman, 09:34)

The Hosts React

• Hosts tease Dorman’s choice of food and his continued family traditions.
• The date's abrupt end sparks debate on whether it was a "vibe killer" or just unfortunate, relatable timing.

  “My point was that you don’t think of chili as a really romantic food...” (Brooke, 07:18)
  “It could happen to anybody.” (Jeffrey, 10:26)

Contacting Yolanda: The Truth Comes Out

Initial Confusion & Reluctance

• Yolanda is confused and slightly unsettled by the radio call, hesitant to discuss her date on air.

  "It's weird because there's, like, I don't even know how many people are on the phone, and you're asking me about details from a date..." (Yolanda, 13:48)

The "Red Flag" Revealed (14:33–15:41)

• The real dealbreaker: Dorman volunteered that he hadn’t been with a woman romantically in three years, then added, looking her dead in the eyes, “I hope that can change soon.”

  "He brought up the fact that he hadn't been with a woman romantically in three years...Then he...looked me dead in the eye, and he's like, 'I hope that can change soon.'" (Yolanda, 14:33)

Awkward Admission Escalates

• Dorman, listening in, tries to explain, blaming nerves, chili, and “truth serum” effect.

  "We were having chili. I don't know. I just rambled." (Dorman, 16:19) “Chili brings up…” (Jeffrey, 16:24)

• Yolanda’s discomfort grows with each TMI revelation—including the mention of his mom discussing her own physical relationship with his dad.

  "You tell your mom about your lack of intimacy?" (Yolanda, 17:42)
  "She just tells me that, like, her and dad do it more often." (Dorman, 17:45)

• The hosts try to salvage the interaction, joke about changing cuisines for the next date, but Yolanda firmly declines.

  “Would it change your mind at all if it's not chili?” (Brooke, 19:48) “No. I can't believe you ask that.” (Yolanda, 19:51)

Notable Quotes & Memorable Moments

• "You can't spell desperation without Brooke and Jeffrey in the morning." (Brooke, 04:29)
• "I picked this spot...known for their chili...world famous." (Dorman, 07:01)
• "There's a tradition...every Friday before I go to work, I go to my mom's place...she always, like, packs my lunch for me." (Dorman, 08:14)
• "He just said it to me, and he...looked me dead in the eye...I hope that can change soon." (Yolanda, 14:47)
• "You telling women that makes it even less likely to happen." (Yolanda, 17:31)
• "My mom says the same thing." (Dorman, 17:39)
• "At this point, guys, I'm sorry. I'm getting nervous again. Rambling...Even when I was getting it three years ago, it wasn't that great..." (Dorman, 19:14)
• "I hope you don't. Then you'll know what it feels like." (Dorman, 18:13)
• "Far too open for anybody to be comfortable with." (Brooke, 20:08)

Important Timestamps

• 04:29 – Segment officially begins, Dorman’s intro.
• 05:36–06:09 – Dorman discusses meeting Yolanda and her memorable dating profile.
• 07:01–07:32 – The chili restaurant chosen as a date spot.
• 08:14–09:28 – Dorman’s relationship with his mom and the infamous lunch tradition.
• 09:34–10:02 – The date’s abrupt end due to chili trouble.
• 13:14 – Yolanda is called and recalls the date.
• 14:33–15:11 – Yolanda reveals the big red flag: Dorman’s TMI confession.
• 16:00–17:45 – Dorman joins the call and the awkwardness crescendos.
• 17:45–19:28 – Dorman reveals another layer about his parents’ intimacy; situation spirals.
• 19:39–19:57 – Brooke offers a new date; Yolanda firmly declines.
• 22:31–23:29 – Post-mortem discussion by the hosts.

Episode Recap and Takeaways

• Central Theme: Vulnerability and oversharing can tank even a promising start. Dorman’s candid admission about his romantic dry spell and his family’s openness went too far for Yolanda.
• Hosts’ Tone: Fast-paced, relentlessly teasing, but not unkind. They balance empathy for Dorman’s earnestness and laughter at the spiraling awkwardness.
• Final Outcome:
  • No second date granted.
  • Consensus is that Dorman is well-meaning but needs boundaries—and perhaps a new lunch tradition.
  • Hosts encourage listeners to reach out with their tough dating situations (and joke that maybe someone out there wants to meet Dorman!).

  "We all wish you a lot of luck getting over your hill that you're trying to climb here." (Brooke, 20:21)

For those not listening:
This episode is a front-row seat to the perils of nervous oversharing, chili-fueled confessionals, and the laugh-out-loud, cringe moments that make Second Date Update a must-listen for fans of dating chaos.