Brooke and Jeffrey: Second Date Update

Episode Title: #4 Second Date Update of 2025: After Date Double Date
Release Date: December 26, 2025

Episode Overview

This episode features Brooke, Jeffrey, and the team as they conduct their famously awkward and entertaining “Second Date Update” segment. Listener Justin seeks answers after being ghosted by his date, Tracy, following a first date that included an accidental sleepover—prompted by a suspiciously slashed tire. As the team digs deeper, a shocking twist about Justin's true motives comes to light, sparking a debate on boundaries, honesty, and what counts as a major red flag in dating.

Key Discussion Points & Insights

The Setup: Double Date… with a Twist

• Mini Golf Misadventure
  • Justin shares he met Tracy on Hinge and arranged a fun, interactive first date at mini golf.
  • Justin tried to prank Tracy by hiding behind a fake mountain as a joke, but overheard her say, “Did I seriously just get ditched again on a date?” This highlighted Tracy’s past bad experiences and momentarily made things awkward.
    • Brooke: “You can’t jump out and yell surprise after she says that out loud.” (05:58)
  • The situation is quickly smoothed over and they both end up laughing about it.

The Tire Incident

• Post-Date Trouble
  • After the date, Justin discovers his car tire is slashed outside Tracy’s apartment, in what he claims was a random act (07:21).
  • Feeling uncomfortable waiting alone in a “not great neighborhood,” he’s invited back into Tracy’s apartment while waiting for AAA.
  • Justin spends the night (on the couch), and he and Tracy share bagels, orange juice, and a kiss the next morning, which Justin takes as a positive sign (08:33).

Suddenly, He's Ghosted

• Lack of Contact
  • Despite what Justin perceives as a successful date-turned-sleepover, Tracy ceases responding to his texts and calls (10:21).

Confronting Tracy (The Second Date Update Call)

• Tracy Answers the Phone
  • The hosts reach out to Tracy to investigate why she ghosted Justin.
  • Tracy hints at “sketchy things” and reveals she feels she was lied to, stating, “I caught him in a lie. That’s why I’ve not been calling him back.” (13:25)
• Shocking Reveal: Slashed Tire Was No Accident
  • Tracy discloses that her apartment manager shared surveillance footage showing Justin slashing his own tire in her parking lot with a street light shining directly overhead (14:08).
    • Tracy: “There was a streetlight right over the car, and you could see very clearly that it was him.” (14:21)
  • She is disturbed by Justin’s manipulation and says, “I can’t believe someone would stoop to that level.” (15:57)

Confronting Justin (On-Air)

• Justin’s Admissions

  • Initially surprised, Justin confesses, “I didn’t see any cameras out there… that’s on me, I guess.” (15:36)
  • He rationalizes his actions: “It was probably one of the best dates I’ve had in a really long time. And that’s why I did it. I wanted to spend more time together.” (15:44)
  • Justin discloses this wasn’t his first time using the tire-slash tactic, having done it once before during a breakup attempt (16:59).
    • Brooke: “Have you done this more than once?”
    • Justin: “I did this one other time, and that was only when we were six months together...”

• Team's and Tracy's Reaction

  • The hosts and Tracy are appalled, labeling Justin’s actions as creepy and manipulative.
    • Tracy: "I felt really bad because this happened in my neighborhood... now listening to his excuses... that was really, really kind of creepy." (16:25)
    • Brooke: “No one in the history of the world has ever thought slashing tires is cute.” (16:20)
  • Tracy points out, “You should have spent $250 maybe taking me out on the date the next time. Because I would have said yes.” (18:06)
  • Justin remains unfazed: “You guys are acting like I committed murder or something. I mean, I literally slashed my own tire. Get over it, guys.” (18:11)

Closing Thoughts

• Zero Chance for a Second Date
  • Tracy stands firm on not wanting to see Justin again, citing a complete boundary of trust.
  • The hosts continue to rib Justin about his ‘romantic’ strategy and joke about writing a guide on “How to Spot a Psycho.”
    • Jeffrey: “Let’s give him credit for not murdering on the first date, okay? He deserves credit for that.” (18:17)
    • Brooke: “I can’t believe we’re looking at murder red flags right now. But I’m pretty sure this is one of them.” (18:23)

Notable Quotes & Memorable Moments

• Brooke (on mini golf): “You do it, but you’re not into it.” (05:01)
• Justin (confessing): “It was probably one of the best dates I’ve had in a really long time. And that’s why I did it. I wanted to spend more time together.” (15:44)
• Tracy (on slashed tire): “There was a streetlight right over the car, and you could see very clearly that it was him.” (14:21)
• Brooke (reacting): “No one in the history of the world has ever thought slashing tires is cute.” (16:20)
• Justin (unapologetic): “You guys are acting like I committed murder or something. I mean, I literally slashed my own tire. Get over it, guys.” (18:11)
• Tracy (final verdict): “Unfortunately, I think that this one’s definitely a no go.” (18:44)
• Jeffrey (sarcastic wrap): “Let’s give him credit for not murdering on the first date, okay?” (18:17)

Important Segment Timestamps

• [02:48] – Episode begins: #4 Second Date Update intro
• [03:36] – Justin explains how he met Tracy and their mini golf date
• [05:29] – The mini golf hiding incident and Tracy’s reaction
• [07:21] – Justin discovers his ‘slashed’ tire
• [08:33] – Justin describes the sleepover and morning with Tracy
• [10:21] – Justin explains Tracy ghosting him
• [11:35] – Hosts call Tracy
• [13:25] – Tracy reveals she caught Justin in a lie
• [14:08] – The surveillance footage bombshell
• [15:36] – Justin confesses and tries to justify his actions
• [16:59] – Justin admits he’s slashed his own tire before
• [18:06] – Tracy rebuts, saying he could’ve just asked for a second date
• [18:44] – Tracy says definitively, “This one’s definitely a no go.”
• [21:00+] – Hosts debrief and joke about writing “How to Spot a Psycho”

Tone, Language & Style

The episode maintains its characteristic blend of humor, gentle roasting, and empathy for both guests—though the team’s patience for Justin’s “romantic strategy” is in short supply by the end. Tracy’s perspective is treated with seriousness, signaling strongly to listeners where healthy dating boundaries lie.

Summary

In this installment of Second Date Update, an initially quirky story of mini-golf and misadventure takes a disturbing turn when surveillance footage reveals Justin staged a tire-slashing to prolong his time with Tracy. Despite his attempts to play it off as a romantic gesture, the hosts—and Tracy—are united in calling out his manipulative and deceitful behavior, ultimately dismissing any chance of a second date.

Listeners who enjoy cringe-worthy honesty, wild dating stories, and playful but pointed commentary will find this episode highly entertaining and a cautionary tale for the age of creative courtship.