Podcast Summary: "Second Date Update Classics: 3rd Times a Yawn + Super Kid Shames the Day"

Podcast: Brooke and Jeffrey: Second Date Update
Release Date: December 13, 2025
Host: iHeartPodcasts / Main hosts: Brooke, Jeffrey, Alexis, Jose

Overview

This episode of "Second Date Update" features two classic, back-to-back segments where the hosts help listeners navigate the confusing aftermath of first dates gone awry. With their signature mix of playful banter, real talk, and cringe-worthy confessions, Brooke and Jeffrey explore the pitfalls of modern dating apps, reverse psychology, and the perils of accidental insults.
Main Segments:

1. "3rd Times a Yawn" — A 'nice guy' tries to break the friendzone curse through risky strategy.
2. "Super Kid Shames the Day" — A promising dinner derailed by awkward compliments and a pint-sized superhero.

1. "3rd Times a Yawn" – Nice Guy Tries a Bold Move

Segment Theme

Can a bona fide nice guy flip the script and become irresistible using reverse psychology? (03:27)

Key Discussion Points

• Dating App Fatigue & Too Many Choices (04:15–05:31)

  • Hosts discuss overwhelming choice in online dating.
  • Brooke: "I go to the cereal aisle, and it feels overwhelming with what one I should choose." (05:16)

• Evan's Dilemma: Always Friendzoned (05:31–07:23)

  • Evan, the listener, admits to being "one guy in a sea of a billion dudes."
  • He's been dating multiple women but gets friendzoned after promising first dates.

• Evan's Plan: Reverse Psychology (07:39–09:18)

  • Evan wants the hosts to call Jenna (his date) and tell her he's "on the fence" about a second date—hoping she'll chase him instead.
  • Brooke is skeptical: "Try not to think game. He's playing games in my head right now." (07:36)
  • Evan: "It's not a game, but it is reverse psychology." (07:39)

• Hosts Challenge Evan’s Strategy (09:43–10:21)

  • Jeffrey thinks the idea sounds manipulative but is curious about the outcome.
  • The hosts agree to go along for "entertainment purposes." (10:40)

Notable Quotes & Moments

• Evan Explains His Frustration:

  • "I've had a lot of dates...where the first meeting's great, but then it just—fizzles out." (08:19)
  • "...the girl will say to me, hey, you're super cool and everything, but there's just not a strong enough of a connection for me." (08:28)

• On Being Honest:

  • Brooke (on potential backfire): "You do know this could backfire, right?" (09:14)
  • Evan: "I have nothing to lose at this point, trust me." (09:18)

[11:02] The Call with Jenna

• Jenna Takes the Bait, Briefly Confused (13:38–15:04)

  • Hosts tell her Evan is "on the fence."
  • Jenna: "I thought we liked each other—I thought everything was..." (14:28)
  • When prompted about the date: "Well, we grabbed drinks...He was super, super nice...I don't really go out with nice guys." (15:07)

• Evan Attempts to Play Hard to Get—Fails Spectacularly (15:53–18:39)

  • Evan goes in-character: "I'm just not totally sure that there's a romantic connection between us."
  • Jenna, unimpressed: "I guess maybe we're just better off friends." (16:18)
  • After more awkwardness and prompting, Evan breaks character, admits his real feelings, and explains his plan.
  • Evan: "I really like you...I was afraid that if I just carried on being nice and showing that I really like you, that you would get bored of me." (19:13)

Outcome

• Resolution: Honesty Wins
  • Jenna agrees to another date only after Evan finally drops the act.
  • Brooke: "No, the honest truth works, Jeff. Your real feelings work." (20:22)
• Hosts Reflect:
  • "It's a win for nice guys everywhere. And he's lucky that for some weird reason, she just liked him for who he was." (22:09)

2. "Super Kid Shames the Day" – Compliment Catastrophes

Segment Theme

How can one well-meaning compliment destroy your chances at love? And what happens when a kid in a cape adds to the chaos? (23:40)

Key Discussion Points

• Fast-Tracking a First Date (24:09–26:28)

  • Gabe and Abby agree to meet after just two app messages.
  • Gabe: "I agree with you. Let's not get stuck on this app and text. Let's meet in person." (25:52)

• Impromptu Child Interaction Sparks Hope (27:41–28:25)

  • On the date, a little boy in a Superman cape interrupts. Abby plays along, impressing Gabe.
  • Gabe (internally): "Maybe this would be a great mom, the future MILF." (28:19)

• Promises vs. Reality (28:37–28:54)

  • Date seemingly ends well; Abby replies “We’ll see” when asked about a second date—but then ghosts Gabe.

Notable Quotes & Moments

• Why Didn’t She Call Back?

  • Abby: "He said a bunch of things that were pretty off-putting to me, and I'm just gonna leave it at that." (33:06)
  • First complaint: "You look nice in this light." (33:32-33:44)
    • Abby: “There was no light. It was super dark where we were. Like, I look nice in the dark?” (33:44)
  • Second: "I bet you're so pretty that the guys online are throwing themselves at you." (34:07)
    • Abby: “Like… I have nothing else to offer except my looks, like come on.” (34:26)
  • Third: She’s insulted when Gabe praised her kid-friendliness: “He was, like, so impressed that I’d shockingly be good with kids. Like, of course I’m good with kids.” (35:05)

• Gabe Responds (Poorly):

  • "I don't remember you having an ego like you do now. Maybe you have some insecurity issues, I don't know." (36:13, 36:20)
  • Tries to compliment: "You are remarkable. You are gorgeous and an incredible soon-to-be mother..." (37:46)
  • Abby (cutting him off): "What, do I look fat now too?" (38:03)

Outcome

• Abby Shuts Down Further Dates:
  • "I've heard enough, honestly. This has been enough. I didn't need to engage in it a second time, quite frankly. So I’m gonna go." (38:11)
  • Both agree a second date is a “hard pass.” (39:16)
  • Gabe (humorously): "I mean, if you guys are paying, I wouldn’t mind that. That’d be nice…by myself." (39:28)

Hosts’ Takeaways

• On the Dangers of Bad Compliments:
  • Brooke: "Next time you go out with a woman...maybe you just try not to shame her all the time." (38:22)
  • Jeffrey interprets: “Men have a hard time expressing what they really feel inside...He’s deeply apologetic.” (36:50)
• Brooke’s Reflection:
  • "This would happen if they texted before they went out on a date." (39:10)
• Jeffrey’s Wisdom:
  • "It's a nice dude. Be a nice dude. It's a win for nice guys everywhere." (22:09)

Top Quotes with Timestamps

• “You sound like a genuinely nice guy, and that's probably why this is happening.” – Brooke (09:03)
• “I have nothing to lose at this point, trust me.” – Evan (09:18)
• “I was afraid if I just carried on being nice and showing that I really like you, you’d get bored of me.” – Evan (19:15)
• “No, the honest truth works, Jeff. Your real feelings work.” – Brooke (20:22)
• “He said a bunch of things that were pretty off putting to me, and I’m just gonna leave it at that.” – Abby (33:06)
• “You look nice in this light.” – Gabe, cited by Abby (33:37)
• “What, do I look fat now too?” – Abby (38:03)
• “Word of advice: next time you go out with a woman...maybe you just try not to shame her all the time.” – Abby (38:22)

Timestamps for Important Segments

• [03:27] – Introduction to Evan’s case and dating strategy
• [07:39] – Evan introduces the “reverse psychology” plan
• [11:02] – Second Date Update call with Jenna
• [13:38] – Jenna expresses confusion and disappointment
• [19:13] – Evan comes clean about his feelings and plan
• [20:18] – Jenna agrees to second date
• [23:40] – Super Kid segment intro
• [27:41] – “Super Kid” moment and expectations set
• [33:06] – Abby explains her reasons for rejecting Gabe
• [36:20] – Gabe’s awkward defense and failed apology
• [38:22] – Abby delivers her final advice
• [39:16] – Both parties hard pass on another date

Summary & Takeaways

• The episode underscores the confusion and miscommunication rampant in modern dating. Reverse psychology, “negging,” and attempts to appear aloof don’t work—but genuine honesty and directness occasionally can.
• The hosts reinforce that being yourself is still the best (and least cringe-worthy) path to romantic success, and that forced mind games or accidental insults most often just create more problems.
• Listeners are left laughing, occasionally wincing, with plenty of “what not to do” lessons from real-world dating disasters.

For more Second Date Updates, check out Brooke and Jeffrey on iHeartRadio, Apple Podcasts, or Spotify.