Brooke and Jeffrey: Second Date Update – “The Last Hopeful Dater, Jeff’s Mom’s High Speed Chase & Alexis’ Car Casino”

Podcast: Brooke and Jeffrey: Second Date Update
Episode Date: December 7, 2025
Episode Theme: A riotous full-show episode featuring Black Friday aftermaths, streaming superstars, holiday confessions, a car chase, family gambling interstate escapades, and a hilariously awkward “Second Date Update” with an unbreakably optimistic dater.

Episode Overview

This episode is loaded with quintessential Brooke and Jeffrey group banter, offbeat takes on current trends (from Cyber Monday stats to streaming musicians), personal Thanksgiving misadventures, and the show-stopping “Second Date Update” titled “The Last Hopeful Dater.” Expect high-energy, playful exchanges centered on the funny, weird, and often cringe-worthy realities of modern life and dating.

1. Gratitude & Cyber Monday Confessions

Timestamps: 00:00 – 03:37

• Spotify Wrapped: The team celebrates their show hitting #3 on Spotify’s podcast chart, thanking fans for tagging them on social media, with a running joke about being just behind “Big Booty Mix.”
• Cyber Monday Shopping: The group swaps stories about their Black Friday/Cyber Monday hauls. Curtain rods, TVs, and HBO Max subscriptions get shout-outs, with banter over shopping during work hours and a breakdown of this year’s record-smashing $14.2 billion in spending.
• Memorable Quote:
  • Brooke: “I totally didn't do it during work hours.” (02:46)
  • Jeffrey: “Why battle the crowds when you can just shop from your bed — or in Brooke's case, the toilet.” (03:24)

2. Pop Culture Game – Streaming Supreming (Most-Streamed Artists)

Timestamps: 03:47 – 08:48

• Game Segment: The group tries to guess the top 10 most-streamed music artists of all time. Artists named include Taylor Swift (#1), Bad Bunny (#2), Justin Bieber, Kanye West, Drake, The Weeknd, Ariana Grande, Ed Sheeran, Eminem, and Post Malone.
• Memorable Exchange:
  • Host (re: Taylor Swift): “That is insane!” (06:00)
  • Jeffrey (deadpans): “Give me The Beatles. Streaming…” [incorrect guess, group erupts] (08:00)
• Punishment: Alexis is chosen to sing “Shake It Off” by Taylor Swift as a forfeit, post-game. (09:16)

3. Thanksgiving Recaps & Family Fails

Timestamps: 10:03 – 18:15

• Brooke’s Fit Family: Brooke regales listeners with tales of her husband's health-obsessed family: “They’re all turkey trotters... and then we come home and they only cook three potatoes for twelve people.” (11:34)
• Jose’s Middle-School Comedy Challenge: Jose shares a disastrous attempt to win over his nephew’s friends with “cringe” jokes. “Literally ate the worst pile of poo I’ve ever done on stage.” (14:46)
• Alexis’ Interstate Car Casino: Alexis describes parking with her family just across the state line to legally play app-based slots in grandma’s minivan—winning $200.
• Jeff’s Mom’s High-Speed Chase:
  • Jeff’s parents, visiting for Thanksgiving, spot the station SUV on the freeway, try to chase it down for a photo, and end up in an unintentional car chase, prompting his mom to write an angry email to the station.
  • Jeffrey (sarcastic): “My mom hates you. Congratulations.” (18:11)

4. Listener Textboard & Audience Interactions

Timestamps: 18:15 – 19:59

• Listeners text in their Thanksgiving and weather complaints, including binge-listening tales and odd stories (“I’m a six-year-old guy from Houston…”), prompting the hosts to riff affectionately on their audience’s oddities.

5. Busted – Hilarious Holiday Cheating Stories

Timestamps: 20:03 – 27:33

• Vignettes from Listeners:
  • Nathan: Finds his girlfriend half-naked with a retiree in a tool shed, after neighborhood watch alerts across the community. (22:50)
  • Cassidy: Hears his girlfriend leave voicemails on a dating podcast, then catches her lying about “being at yoga” while meeting another woman. (24:59)
  • Gustav: Girlfriend disappears at a wedding, emerges from a photo booth with hickeys; excuses range from “dog attack” to “allergic reaction to a feather boa.” (26:35)
• Memorable Quote:
  • Brooke: “This is the difference between a guy catching a cheater and a woman. We would search that photo history on the machine.” (26:54)

6. Phone Tap – The Tarp Roof

Timestamps: 27:45 – 33:09

• The show prank calls a woman whose husband set her up, tricking her into believing that, for $6,000, workers have zip-tied plastic wrap over her roof as a “fall special.” The caller ups the absurdity with offers of an “extra layer of plastic for winter” and “zip ties NASA uses” before revealing it’s a joke.
• Quote:
  • Victim (frantic): “You can’t even put a shingle on—this whole thing is a scam!” (30:58)

7. Second Date Update: “The Last Hopeful Dater”

Timestamps: 33:09 – 49:50

Setup:

Unfailingly positive listener Claire is concerned when James, a man she had a magical first date (bowling + butterfly house), disappears after three days of back-and-forth texts and vague, work-related non-answers. She fears something’s happened to him, as “he just doesn’t seem like the type who would ghost.”

• Claire’s Naivety: The group repeatedly struggles with Claire’s relentless optimism, continually warning her that her “vibes” might be misleading:
  • Jeffrey: “What if we find out after we call that he actually blew you off?”
  • Claire: “He wouldn’t do that. There’s no way!” (39:02–39:27)
• The Reveal (James’ Perspective):
  • James answers, immediately groaning at Claire’s mention: “Oh my goodness… what is she doing?” (43:32)
  • Explains Claire was excessively eager—if he said he was busy Tuesday, she’d ask about Wednesday, Thursday, Friday…
  • The real shock: Claire called his HR department requesting a “welfare check” and suggesting they lighten his workload so he could date her.
    • James: “I had to meet with my HR department… you’re messing with my job!” (46:39)
• Claire’s (Cringey) Defense:
  • “If caring is a crime, then I’m guilty… no other girlfriend would do that for a guy.” (46:08, 46:22)
  • The group recoils: “Why did you say girlfriend? You’re labeling it.”
• Resolution:
  • Jeffrey (deadpan): “So, James, what do you think about giving Claire one more chance?”
  • James (firm): “No. No, no, no.” (49:09)

Memorable Quotes & Exchanges:

• Brooke: “That is a HUGE boundary to cross. You just never call someone’s workplace.” (47:14)
• James: “Please listen to them—care less about me. Care less about other people.” (49:37)

8. Post–Second Date Analysis

Timestamps: 49:53 – 50:57

• Brooke, Jeff, and the rest ponder Claire’s indestructible optimism, even after unequivocal rejection and her disturbing lack of self-awareness.
• Alexis predicts: “I feel like we’re going to hear from her again. It’s not going to be her first ghosting.” (50:34)
• Jeffrey sums up: “We’re all just jealous of her relentless optimism… that’s exactly what you need to survive this dating world.” (50:38)

9. Lightning Segments: Quick Laughs and Trivia

Timestamps: 51:14 – End

• Passwords: The team riffs on password trends (admin, 123456, brand loyalty), roasting one another’s supposed choices and the increase in profanity passwords. (51:14–53:25)
• Laser Stories: Absurd headlines (Tesla vandalism, Amazon’s 30-min delivery test, Dole’s new coconut-y pineapple, fun cities ranking) round out the laughs. (53:25–60:10)
• Trivia Grinch (Win Brooks’ Bucks): A listener, Stephanie, takes on Brooke in a holiday quiz, recalling AirPods at White Elephant parties and the intricacies of Harry Potter’s forehead scar. (61:15–66:45)

Notable Quotes

• On Relentless Hope:
  • Claire: “If caring is a crime, then I’m guilty. I just care about you.” (46:08)
  • James: “You’re not my girlfriend. We hung out once. What are you talking about?” (46:30)
• On Family Madness:
  • Jeff: “My mom would disagree… she wrote an angry email to our radio station saying the driver was very rude. Really? That’s the way you treat your fans?” (17:43)
• On Modern Dating Reality:
  • Brooke: “That is a HUGE boundary to cross. You just never call someone’s workplace.” (47:14)
  • Jeffrey: “And that’s the message we’re going to leave today: Care less about everyone.” (49:43)

Top Segments & Timestamps

• Cyber Monday Stats/Banter: 01:06–03:47
• Pop Music Streaming Rankings Game: 03:47–08:48
• Thanksgiving Family Antics: 11:18–18:15
• Second Date Update – “The Last Hopeful Dater”: 33:09–49:50
• Phone Tap – Roof Plastic Wrap Prank: 27:45–33:09
• Listener Busted Stories: 20:03–27:33
• Password Trends & Laser Stories: 51:14–60:10

Summary in a Nutshell

This episode is a boarding pass to Brooke and Jeffrey’s irreverent universe: full of quirky personal tales, sharp pop culture games, and the ultimate cautionary tale of crossing boundaries in dating (Claire’s well-intentioned, yet catastrophically overbearing optimism). The hosts’ charm and comedic chemistry fuel each section, making it a feast of relatable laughs and facepalm-worthy moments.

For New Listeners:
Don’t ghost on this episode—it’s a prime example of the show’s hilarious group dynamic and how not to get a second date (and how not to help your hopeful friend). Enjoy the chaos!