Brooke and Jeffrey: Second Date Update (Full Show)

Episode Title: Jeff’s Big Pumpkin Parody, Rank Me Date + Scariest Haunted House EVER
Air Date: October 19, 2025

Brief Overview

This episode of Brooke and Jeffrey in the Morning is packed with Halloween spirit and signature comedic banter. The team celebrates Jeffrey’s birthday with a special trivia segment, dives into bizarre and hilarious Halloween news (from pumpkin contests to Starbucks trends), discusses the country’s scariest haunted house, hosts their classic “Second Date Update,” and debuts Jeffrey's brand new “Big Pumpkin” song parody. As always, fun, wit, and a dose of the ridiculous keep the energy high for the full hour.

Key Segments & Discussion Points

1. Opening Banter & Listener Comments (00:00–03:22)

• Theme: Halloween obsessions, show inside jokes, and pickleball.
• Notable Themes: Halloween candy confessions, pickleball mishaps, global podcast listeners.

Quote:
Brooke (00:54): "Listen, we're not playing to be good. We're playing for enjoyment, for fun."
Jeffrey: "Yeah, it's like the show."

2. Shot Caller Trivia – “Jeffrey Uncovered” Birthday Edition (03:22–09:19)

• Host: Jake, with themed questions about Jeffrey as part of his birthday celebration.
• Highlights:
  • Questions about Jeffrey’s middle name, celebrity crush, family pet, and his preference for a walk-on song.
  • Brooke jokes about her paycheck size, and Jeffrey reveals his real celebrity crush was Hilary Duff.
  • Ends with the team singing “Happy Birthday” to Jeffrey with a “Hava Nagila” chair-lifting twist.

Quote:
Jake (03:34): “Well, today is no ordinary day, my friends. Cause it’s the birthday of the man, the myth, the boy with the throat as golden as his family trust fund.”
Jeffrey (09:09): “Hilary Duff would have sang it better.”

3. News Updates: Pumpkin Contests, Odd Halloween Trends, and Laser Stories (09:25–19:42)

a) World’s Biggest Pumpkin (09:32–11:17)

• Story: Brandon Dawson wins with a 2,436 lbs pumpkin.
• Prize: $21,000+.
• Discussion: Dreams of making a walk-in jack o’lantern.

Quote:
Brooke (11:15): “You could walk inside it—yeah, that would be so smelly.”

b) Laser Stories Segment (11:50–19:42)

• Format: The team reacts to odd/quirky news around Halloween.
• Stories include:
  • Fake license plates in California (creativity gets a ticket; 12:34)
  • Grubhub’s “Snooze Insurance” for missed deliveries—mainly targeting college students (14:25)
  • Influencers bringing hollowed pumpkins as mugs to Starbucks and how it’s received (16:18)
  • Halloween candy odds: Reese’s PB Cups most common, rare toothbrushes, and fruit snacks replacing candy (18:01)

4. Segment Highlight: Scariest Haunted House in America (19:46–28:13)

• Discussion:
  Jeffrey introduces the horrifically intense haunted house, rumored to be the scariest in the country—possibly illegal and requiring grueling waivers.
• Details:
  • Located in San Diego; waitlist of 27,000, only 50 participants a year.
  • 40-page waiver, including warnings about physical/psychological torture: “teeth extracted, tattooed, fingernails removed.”
  • Requirement to participate: Doctor’s note, background check, drug test, and no swearing allowed.
  • Two-hour documentary orientation before.
  • No one has ever completed the eight+ hour experience.

Quote:
Jeffrey (23:06): “It basically says you give them consent to do whatever to you.”
Brooke (23:33): “What is wrong with, with this country that people are so starved for an adrenaline rush that they need to go get their fingernails out?”

Memorable: Alexis is horrified, Jake cracks wise about ex-wives describing the haunted house owner as “a dangerous predator.”

5. Phone Tap Prank: “Hi, Robin!” (28:34–33:41)

• Scenario: Jeffrey calls a woman (Karen) about her missing Amazon order – the catch is, her drone delivery (named Robin) is hovering overhead. She’s coaxed into waving and shouting “Nihao, Robin” in public to “receive” her package.
• Comedy: Karen gets increasingly flustered as she’s made to shout out phrases in her yard. The prank is revealed by Jeffrey.

Quote:
Karen (32:27): “Nihao Robin. Nihao Robin. Are you happy? I’ve made a fool of myself.”

6. Second Date Update: “Rank Me Date” (33:48–52:09)

• Story Recap:
  • Sierra and Ashwin go from rooftop bar plans (thwarted by a cryptocurrency event) to bonding in a greasy old diner and finally winding up at his place.
  • During intimate conversation, Sierra asks Ashwin to “rank” her; he says “top three,” and she quips he’s “top five.” When pressed, Sierra admits she’s only been with five people—making her compliment less flattering.
  • Ashwin felt “humiliated” and ghosted her. Sierra says she was trying to be playful/flirty, not mean.
  • Both apologize sincerely for their roles—refreshingly mature. They agree to another date.

Notable Quotes:
Ashwin (44:15): “It was probably one of the most amazing dates I’ve ever been on.”
Sierra (47:53): “I feel so bad… I was trying to be kind of cocky and flirty.”
Brooke (50:07): “Don’t let your pride stand in the way of this one, Ashwin.”

7. Song of the Week: “Big Pumpkin” (Parody of Jay-Z’s “Big Pimpin’”) (52:12–59:31)

• Jeffrey’s Halloween Parody:
  A tongue-in-cheek rap about the commercialization and joy of pumpkin patch outings, from overpriced hayrides to farm animal kissing booths and grocery store pumpkins.
• Refrain: “Big pumpkins, full of seeds… big pumpkins every Halloween…”

Quote:
Jeffrey (55:02): “Once you get out there and you experience the pure joy of trudging through a muddy field on an ice cold day, paying quadruple the price of grocery store pumpkin that they pulled from this exact same field just a week ago…”

8. Game Segment: Win Brooke’s Bucks – Game 7 (59:42–65:15)

• Contestants: Brooke vs. Garrett (tied series, tiebreaker)
• Trivia includes:
  • Largest pasta producer (China, not Italy!)
  • Plasma as the liquid part of blood
  • Super Mario bad guys
  • ‘Encanto’ as source of "We Don't Talk About Bruno"
  • Hades, god of the underworld
• Result:
  Garrett wins with 5 correct; Brooke only gets 3.

Notable Quotes & Moments (with Timestamps)

• Jeffrey on Podcast Listeners:
  “It is interesting how people catch us on all these different platforms.” (01:18)
• Brooke on Playing Pickleball:
  “Listen, we’re not playing to be good. We’re playing for enjoyment, for fun.” (02:54)
• Jake, introducing Jeffrey’s birthday:
  “It’s the birthday of the man, the myth, the boy with the throat as golden as his family trust fund.” (03:34)
• Jeffrey’s Pumpkin Parody Setup:
  “Now they’ve made it into this whole experience with like corn mazes and hay rides and cinnamon donut shops…” (54:19)
• Jeffrey about the Haunted House:
  “It basically says you give them consent to do whatever to you.” (23:06)
• Second Date Category “Ranking”:
  Ashwin: “I already felt so vulnerable. You know, we’re in my bed naked, and we’ve just been together.” (47:13)

Timestamps of Key Segments

• Opening & Listener Banter: 00:00–03:22
• Shot Caller: Jeffrey’s Birthday Trivia: 03:22–09:19
• Pumpkin Contest Story: 09:32–11:17
• Laser Stories Segment: 11:50–19:42
• Haunted House Discussion: 19:46–28:13
• Phone Tap (Karen & Drone): 28:34–33:41
• Second Date Update (“Rank Me Date”): 33:48–52:09
• Song of the Week (“Big Pumpkin”): 52:12–59:31
• Win Brooke’s Bucks (Game 7): 59:42–65:15

Show Tone & Takeaways

The banter is playful, self-deprecating, and peppered with running inside jokes and Halloween themes. The team’s chemistry shines through, especially in riff-heavy segments. Notably, the “Second Date Update” delivers rare emotional maturity as both participants own up to awkwardness, offering a refreshingly honest dating story. Meanwhile, news and song segments blend humor with light satire on modern holiday traditions.

Listen & Social

• Stream the full episode: iHeartRadio | Apple Podcasts | Spotify
• Follow on Instagram: @BrookeandJeffrey