Brooke and Jeffrey: Second Date Update Classics – "Ex-Aversary + Lady In Red"

Release Date: October 4, 2025

Episode Overview

This classic back-to-back "Second Date Update" features two jaw-dropping stories: In "Ex-Aversary," the team investigates why a seemingly perfect first date ends with a shockingly harsh text. In "Lady In Red," a listener’s triumphant return to dating after a broken engagement derails in a way no one could predict—all to the unexpected soundtrack of “Lady In Red.”

These episodes capture the signature hilarious, candid, and at times bewildering tone of the Brooke and Jeffrey show. If you've ever wondered why someone suddenly ghosted after a promising connection, prepare for uncomfortable truths, wild confessions, and more than a few unforgettable quotes.

Segment 1: "Ex-Aversary"

[03:42–22:01]

Key Discussion Points & Insights

• Kendrick's "Perfect" Date

  • Kendrick met Danielle online. Her profile looked “too good to be true,” and he admits doubts before meeting.
    • "Okay, there’s no way she’s going to look like this in real life, right?" (Kendrick, 05:38)
  • In person, Danielle exceeded his expectations: “She looked like she just stepped out of a TV commercial.” (06:28)
  • They enjoyed a classic date: browsing a mall, cracking quirky jokes (not all landing), and sharing a meal at a seafood buffet.

• The Kiss and the Confusion

  • Kendrick proudly shares that their date ended with a small, sweet kiss.
  • The next day, he’s blindsided by a scathing text:
    • "I can't freaking believe you. I don't date low lives. See ya." (Kendrick, 09:07)

• Intervention: The Second Date Update Call

  • Danielle answers but is clearly irritated. She explains that Kendrick crossed a major line by going through her purse (13:10):
    • "I don't like people who go through my personal things and make me feel uncomfortable." (Danielle, 12:58)
  • The item in question? A missing Jamba Juice gift card from her wallet.

• The Shocking Confession

  • Kendrick admits on-air he did take the gift card—but claims intentions were (somewhat) innocent:
    • "I needed it for my ex. [...] We still celebrate our anniversary; we call it an ex-aversary." (Kendrick, 15:51/16:25)
  • The team and Danielle are dumbstruck that Kendrick “borrowed” her gift card as an anniversary present for his ex.

• Escalating Weirdness

  • Kendrick tries to justify his so-called "borrowing," saying he would have reimbursed Danielle—if she’d picked up his calls.
  • The group mocks the absurdity of an “ex-aversary,” and more so, the questionable ethics of purse snooping for a present.
  • Danielle is appalled:
    • "Are your funds that tight? You probably should not have been going out with me." (Danielle, 17:03)

Memorable Quotes & Moments

• Brooke on modern dating hazards:
  "She has a piece of information. I don’t know what it is. She saw something.” (09:40)
• Alexis:
  "You sound like a pickpocket or something, Kendrick.” (17:08)
• Jeffrey (mock-praising):
  "The good point is Kendrick is very detail oriented because he looked at her license." (17:53)

Resolution

• Kendrick apologizes awkwardly, but Danielle is resolute: no chance of a second date.
  • "Oh, you out of your mind? I wouldn’t touch him with a 12 foot pole." (Danielle, 19:02)

Segment 2: "Lady In Red"

[22:18–37:37]

Key Discussion Points & Insights

• RJ’s Return to Dating

  • Newly single after a broken engagement, RJ hasn’t dated in a year until meeting “London” at a happy hour.
  • They feel an instant spark—a connection so rare even Jeffrey jokes:
    • "Do you know how you just instantly feel a connection when you lock eyes with someone?" (RJ, 24:57)
      "Never." (Jeffrey, 24:59)

• A Promising Night

  • Drinks flow, conversation pops, and they end up at London’s place where things turn romantic.
  • The slow dance to “Lady In Red” creates a movie moment—until RJ trips over a coffee table and injures his ankle (26:18–26:36).
  • London is sympathetic: she provides ice; RJ spends the night on the couch.

• The Aftermath—and A Deepening Mystery

  • Oddly, London never checks in on RJ, not even to ask about his injury.
  • RJ is baffled:
    • "Even if you're not interested in someone, you'd still at least check on them. Like, hey, how's your hand?" (Brooke, 27:54)

• Second Date Update Call: The True Story Emerges

  • London's memory of the night is VERY different—she uses the word “freaky” to describe it (32:09).
  • She reveals that after going to bed, she heard “vacuum” noises and groaning coming from the living room in the middle of the night (32:56).
  • London discovers RJ on the couch, vacuum under the blanket “like a tent,” making strange noises. (33:09)
  • RJ protests, finally explains himself:
    • "I looked up online remedies for relieving pain in your ankle. An article said you can use the suction of a vacuum to help stimulate the blood." (RJ, 34:23)

• The Team’s Reaction: Shock, Skepticism, Laughter

  • Brooke, laughs but notes,
    • "Technically he is right if you can get blood flowing around the area. I've never heard of suction, but…" (Brooke, 34:42)
  • London is unconvinced—especially since it was her neighbor’s vacuum and had recently been used for cat messes. (35:00)
  • Alexis (snickering):
    • "I think he helped himself." (36:25)

• Resolution

  • When pressed, London refuses a second date:
    • "It’d be wild for me to turn down a free date, but I think that this is gonna be it.” (London, 37:02)
  • The show concludes, as always, with playful ribbing, advice, and a chorus of disbelief over RJ’s “medical” vacuuming attempt.

Notable Quotes & Moments

• London (on finding RJ with the vacuum):
  "Like, a vacuum underneath a blanket, perched like a tent, and he's making noises.” (33:56)
• Jeffrey (on the night’s madness):
  "This second date update sucks in more than one way, RJ." (37:11)
• Alexis:
  "I want to see the suction marks on his ankle." (39:53)

Important Timestamps

• [03:42] — Start of "Ex-Aversary"
• [06:28] — First impressions: Danielle's TV-commercial looks
• [09:07] — The text: “I don’t date low lives. See ya.”
• [13:10] — Danielle confronts Kendrick on the call
• [15:51]/[16:25] — Kendrick's “ex-aversary” confession
• [19:18] — Danielle rejects the second date

• [22:18] — Start of "Lady In Red"
• [26:18] — RJ’s coffee table mishap, ankle injury
• [32:09] — London’s “freaky” description, vacuum reveal
• [34:23] — RJ’s "vacuum ankle therapy" defense
• [37:02] — London rejects second date, segment close

Takeaways & Themes

• Boundaries Matter: Both stories revolve around unexpected boundary violations—purse-snooping and late-night "vacuum therapy."
• Truth Will Out: Radio reveals tend to elicit unvarnished truths, leading to both humiliating reveals and cathartic closure.
• Classic Brooke & Jeffrey: The hosts keep things light and playful, no matter how unhinged the actual dating behavior gets.

Summary

If you love the “Second Date Update” format—cringe-worthy reveals, dramatic phone calls, and the whole mess of modern dating—this episode delivers big. “Ex-Aversary + Lady In Red” showcase why Brooke & Jeffrey are so beloved: candid guest banter, sharp humor, total unpredictability, and the rare (questionably good) dating advice. Just don’t try vacuum therapy at home.