Brooke and Jeffrey: Second Date Update
Episode: FULL SHOW: The Only Match Date, Jeff’s Celebrity Man Crush + Jose’s $100 Soup (11/12/25)
Date: November 16, 2025
Podcast Host: iHeartPodcasts
Overview
This episode delivers the usual blend of chaos, quirky confessions, dating disasters, and office banter that fans expect from the Brooke and Jeffrey team. The main highlights feature a “Second Date Update” wreaked with mismatched expectations, a cringe-worthy “Battle of the Tinder Dates,” a story about Jose’s epically expensive soup order, and Jeff’s unexpected celebrity man-crush. Interspersed throughout are games, listener texts, and classic slapstick humor. The team also wrestles with technical and personal mishaps—from medical scares at work to recurring coughs—giving the show its characteristic “morning-show energy meets group chat” atmosphere.
Key Segments & Discussion Points
1. Studio Chaos & Banter
Timestamps: 00:00 – 03:38
- The show opens with Brooke, Jeffrey, Jose, and Alexis commenting on the chaos in the studio—people out sick, technical mishaps, Brooke’s glasses breaking, and listener questions about their wellbeing.
- “Her lens keeps popping out mid segment.” — Brooke [00:29]
2. Current Affairs & ‘Karen’ Lawsuits
Timestamps: 03:49 – 09:01
- Updates on bizarre lawsuits involving “Karens” at amusement parks.
- A light roasting on modern Karen antics, dismissed lawsuits, and joke suggestions for improved public signage.
- “She sued the park…because the kids called her a Karen and she felt bullied.” — Brooke [02:32]
- Transition into the playful trivia segment with the “Butler I Hardly Knower” butler-themed quiz.
- Notable moment: Brooke correctly identifies Geoffrey the Butler from “Fresh Prince of Bel-Air”. [06:16]
3. What’s On Your Mind: Thanksgiving, Medical Emergencies, & Expensive Soup
Timestamps: 09:31 – 16:11
- Pre-Thanksgiving anxiety and archetypes at the family table.
- Brooke’s tale of a lackadaisical medical emergency response at their office.
- “Never have a medical emergency here.” — Brooke [11:07]
- Jose’s legendary $100 Panera soup error (accidentally ordering soup from another city via a delivery app).
- “Apparently I ordered it from another city...$115.99 fee.” — Jose [13:31]
- Alexis’s “Friendsgiving” party problems: cold food, not enough silverware, and $5 box wine.
- “Everybody eat with the serving spoons.” — Alexis [15:13]
- Jeff’s story of being star-struck at a party by a former college football player.
- “You're him. You're football guy. I watched you football you him.” — Jeff [17:07]
4. Listener Texts
Timestamps: 18:03 – 19:24
- Reading and reacting to live listener texts about pranks, breakups, compliments, and affectionate nonsense.
5. Battle of the Tinder Dates
Timestamps: 20:08 – 27:37
- Two listeners, Cole (“Self Control Cole”) and Mark (“Tiger Shark Mark”), compete with disastrous first-date stories:
- Chewing “like an alpha,” alphabet soup-only communication, bringing a personal axe to an axe-throwing date, a surprise timeshare pitch, being used as a place-holder at 3:00 a.m. for a Starbucks collectible, and a rooftop stalker-date.
- Most memorable moment: Cole realizes he was used solely as a line-holder for a limited edition Starbucks bear cup, then blocked instantly. [25:29]
- Judges (the hosts) crown Cole as "Desperado Dude of the Week" for being the biggest dating victim.
6. Phone Tap – The Tuxedo Diaper
Timestamps: 27:39 – 33:29
- Jeff pranks a tuxedo rental store, claiming to have left a diaper (and backups) in a rented tux.
- “It was a pretty crazy night…the host was serving cheesecake and even though I’m lactose intolerant, I said, ‘Hey, what the heck, go for it, you’re only 93 once.’” — “Alan Winterbottom” (Jeff) [29:46]
- Escalates with references to Beanie Babies, limo parties, and awkward attempts at flirtation with the employee.
- Revealed as a prank, laughs all around.
7. Second Date Update: The Checklist Disaster
Timestamps: 33:36 – 51:59
- Subject: Corey, a recurring guest, tries to get a second date with Charlotte.
- Corey has an inflexible, oddly specific dating app checklist: sense of humor, brunette (natural, not dyed), mid-to-late 20s, ability to parallel park, and must tolerate him being 5 minutes late to everything.
- He and Charlotte had a great date—she even passed the parallel parking test.
- Charlotte keeps canceling second date attempts.
- The Twist: Charlotte lied about her age to match Corey’s criteria; she’s actually the same age as him (32), but outside his filter.
- “If I did tell you the truth, you wouldn’t even give me a chance.” — Charlotte [47:27]
- Corey reacts poorly, calls her a “granny and a liar,” demands half the dinner back via Venmo, and threatens “Judge Mathis” small claims court for $8.
- “You can tell it to the judge.” — Corey [48:53]
- Result: Charlotte declines a second date—Corey is insulted, defensive, and back to square one.
8. The Top 5 Dating App Lies
Timestamps: 52:02 – 54:38
- The cast guesses the most common lies people tell on dating apps:
- Height
- Loving outdoor activities (hiking)
- Seeking something serious
- Barely using the app
- “That’s just my roommate in the pic”
- Group discussion on authenticity, expectations, and how dating culture’s moved towards “doing it for the plot.”
9. Laser Stories & Win Brooks Bucks
Timestamps: 54:38 – end (~67:00)
- Zany news items: chicken-argument shooting in Florida, the Wicked Witch of the West’s hat is up for auction, Jell-O’s divisive Thanksgiving molds, Target’s new “engagement” policy.
- “Win Brooks Bucks” trivia—Brooke and listener Matthew tie at 5 correct answers, highlighted by quick wit and banter about “super moist turkey” and family recipes.
Notable Quotes & Moments
- Brooke (on office emergencies):
“Never have a medical emergency here.” [11:07] - Jose (the $100 soup):
“Apparently I ordered it from another city...$115.99 fee.” [13:31] - Alexis (Friendsgiving realism):
“So we did have everybody eat with the serving spoons.” [15:13] - Jeff (on being star-struck):
“You're him. You're football guy. I watched you football you him.” [17:07] - Phone Tap (Jeff as Alan W.):
“I think I left my diaper in there.” [29:37] - Corey (Second Date Update criteria):
“They gotta be able to parallel park.” [37:44]
“They gotta be okay with me being five minutes late to everything.” [38:19] - Charlotte (on lying about her age):
“I feel guilty…if I did tell you the truth, you wouldn't even give me a chance.” [47:27] - Corey (post-reveal reaction):
“You went out on the date with me, so. Look, I don't even want to argue about it. I want you…I think it's only fair you Venmo me half the cost of the dinner.” [48:27] - Jeff (on dating plots):
“We're all doing it for the plot.” [51:37]
Host Chemistry, Callbacks & Running Gags
- Studio health chaos: Ongoing coughs, broken glasses, “is Jeff okay?” speculation.
- Brooke as the serial jester/coupon-queen ruining celebrity illusions.
- Group ridicule of bad dating app bios, superficial dating checklists, and “breadcrumbing.”
- Jose’s infamous “Rolando” prank persona.
- Repeated “for the plot” joke as a catchphrase.
Takeaways for Listeners
- The show continues to be a hot mess of lovable personalities, relatable mishaps, and wild dating stories.
- The dangers of being too rigid (Corey’s checklist) or dishonest (Charlotte’s age) in dating.
- Real-life dating is full of surprises, unexpected pitfalls, and plenty of comedy—which is exactly what makes “Second Date Update” a listener favorite.
- The importance of not taking things (or oneself) too seriously, and always “doing it for the plot.”
For New Listeners
This episode embodies the Brooke and Jeffrey signature style: snappy comebacks, audience interaction, embarrassing confessions, and unpredictable dating woes. You’ll be laughing, cringing, and—just possibly—reevaluating your own dating app checklist.