Brooke and Jeffrey: Second Date Update Classics

Episode Title: High Flyer Liar + The Bartender and the Biker
Date: August 16, 2025
Host: iHeartPodcasts

Episode Overview

This double-feature “Second Date Update” episode dives into two classic, uniquely entertaining cases of romantic misadventure. In the first segment, "High Flyer Liar," Anthony seeks the truth after being ghosted by Lisa, whose glamorous persona and surprising secret put a twist on modern dating. The second segment, "The Bartender and the Biker," spotlights Zach, a new mobile bartender who falls for a cycling instructor at an event—and learns that sometimes, enthusiasm isn’t enough to land the date.

Each update pulls back the curtain on dating app facades, perceived slights, and cringe-y missteps, offering laughs and unexpected wisdom for listeners navigating today’s romantic landscape.

Segment 1: High Flyer Liar

Starts: 03:55

Main Discussion Points

• Anthony Returns After Heartbreak
  • Anthony returns to the show post-breakup with Mallory, who he admits left him once he stopped paying for her and her friends’ activities.
    "So with Mallory, I ran out of money." – Anthony (06:02)
• The "High Flyer" Date
  • Anthony meets Lisa, an enigmatic woman he meets through a dating app, distinguished as "High Flyer of the Week."
  • Lisa claims to work private security for celebrities, adding intrigue to her persona.
  • Anthony shares he felt a good connection on their date, noting Lisa’s casual style and charity work.
    "She showed up in Gucci sweats, a Tupac hoodie…" – Anthony (08:29)
• Anthony’s Concerns
  • Lisa’s phone vibrates constantly during their date, making Anthony suspect she is highly sought after on the app.
    "Her phone keeps buzzing the whole time we're together, and… she’s definitely talking to more guys than just me." – Anthony (09:33)
• Reaching Out to Lisa
  • Anthony reveals Lisa has been distant, prompting the call from Brooke & Jeffrey to uncover her side.

Key Quotes & Revelations

• Lisa’s Unexpected Admission (15:01)
  • "Yeah, I just made that up to sound…" – Lisa, confessing that her claim about being a celebrity security detail was a fabrication.
• The Big Twist: Lisa Is the App Owner (15:21)
  • Lisa admits she’s actually a co-owner of the dating platform, not a security professional. Her “High Flyer” badge is part of their marketing feature—she volunteered as the public face.
  • "So I am actually part owner of the dating site…" – Lisa (15:21)
• The Real Reason For Ghosting
  • Using admin access, Lisa had noticed Anthony messaging multiple women despite his claim to be exclusive.
    "As an admin, I can tell that he’s been messaging other women… On the date, he told me… it was just him and I talking." – Lisa (16:34)
• Privacy & Transparency
  • Anthony is taken aback by her ability to view his messages and photos; Lisa insists it’s in the platform’s terms.
    "You can like… see all the messages?" — Anthony (17:54)
    "Yes, I can." – Lisa (18:00)

Notable Moments

• Brooke & Jeffrey’s Reaction
  • Jeffrey and Brooke express surprise at Lisa’s transparency and the ethical questions it raises.
  • Anthony, unfazed, emphasizes his interest in Lisa above all others—even offering to block other matches live on-air.

Resolution (20:02)

Ultimately, Lisa forgives Anthony’s little white lie, and both agree to start fresh with an official second date (on the show’s dime)—even as Lisa jokes about still juggling other suitors: "If I'm being honest, I am still talking to other guys. 14’s on the low side for me." – Lisa (20:21)

Segment 2: The Bartender and the Biker

Starts: 24:55

Main Discussion Points

• Zach’s New Lease on Life
  • Formerly stuck in a dead-end, low-paying job, Zach transitions (thanks to a random bartender’s advice) to running his own mobile bartending business.
  • "You should just quit and start what I'm doing… I could triple my old income." – Bartender paraphrased by Zach (26:22)
• Meeting Bethany at a Party
  • At a combined bachelor/bachelorette party, Zach is smitten by Bethany, a bubbly cycling instructor who helps him out when things get busy at the bar.
• Missed Connections
  • While Zach is proud and chatty about his business success, Bethany later reveals he didn’t show much interest in her own life or ask about her.
  • Bethany also recounts her awkwardness after Zach Venmoed her $20 as a "tip" for helping restock Diet Coke at the party: "He put, here's a tip for the bartender… It just felt really weird and kind of like, you know, creepy old men…" – Bethany (36:29)
• Attempted Second Date
  • Bethany admits she found Zach's focus on himself and misunderstanding of boundaries off-putting. Despite his (and the hosts') efforts to salvage the connection, she sticks to her gut and declines a future date.

Key Quotes & Insights

• On Not Listening
  • "Did you ask her one question that you can remember?” – Jeffrey (38:12)
  • "No, I guess not." – Zach (38:17)
• On Modern "Tips"
  • "It just felt really weird and kind of like, you know, when creepy old men… they like slip you, like, you know, something." – Bethany (36:53)

Notable Moments

• Brooke’s Sympathy for Zach
  • Brooke jokes that if Zach were in-studio, she’d be filling up his “tip jar”—and that his new job ensures plenty of new romantic options, even after this failed attempt.
• Comedic Interludes
  • Jeffrey and Brooke riff on the ironies of dating (a bartender who can’t ride a bike trying for a cycling instructor) and the pitfalls of oblivious self-promotion.

Episode Highlights & Memorable Quotes

• On Modern Dating Lies
  "People lie on dates… it's not so much if you lie, it's what you lie about…" – Brooke (23:12)
• When Two Wrongs Make a Right
  "That's how lies work... Two lies make a right." – Jeffrey (23:59)
• On Moving Forward
  "Sounds like he means well but it's not coming out… Zach, what have you learned from this call?" – Brooke (39:27)

Timestamps for Key Segments

• Anthony’s Situation Recap: 05:30–06:33
• Lisa’s "High Flyer" Persona: 07:06–08:29
• The Big Reveal – Lisa as App Owner: 15:01–15:56
• Lisa Admits Reading Anthony's Messages: 16:34–18:00
• Resolution & Second Date Agreement: 20:02
• Zach Describes His New Bartender Life: 25:43–27:31
• Bethany Recaps Their First Meeting: 28:07–28:58
• Zach's $20 “Tip” Controversy: 36:21–36:44
• Bethany's Explanation for Ghosting: 35:31–36:53
• Final Rejection: 40:20
• Hosts’ Reflections on Dating Lies: 23:12–24:01

Takeaways & Tone

• The episode is classic Brooke & Jeffrey: high-energy, self-deprecating, and punchy, but ultimately empathetic. The hosts use real-life dating absurdities as lighthearted lessons about honesty, boundaries, and paying attention to your date.
• Both segments land on the reality that little white lies and big secrets are par for online dating—but transparency, humility, and actual curiosity remain rare (and valued) currencies.

For more laugh-out-loud updates and to hear more crazy dating stories, listen to "Brooke and Jeffrey" on your favorite podcast platform.