Brooke and Jeffrey: Second Date Update Classics — Pop Some Tags + Love At First Flight

Release Date: January 17, 2026
Podcast: Brooke and Jeffrey
Episode Theme:
A double-header of “Second Date Update” classics, featuring two tales of first dates gone awkwardly off the rails: one centered on a guy’s not-so-subtle hints about his musical past (“Pop Some Tags”), the other about an in-flight spark derailed by unfinished business on the ground (“Love At First Flight”). Both episodes showcase Brooke and Jeffrey’s comedic chemistry as they unravel why things went wrong—and rarely right—when the second call comes.

Episode Overview

This week’s extra-long episode serves up back-to-back “Second Date Update” segments, where the team tries to help listeners who got ghosted after a promising connection. As always, the goal is to get some honest answers—and maybe another date—while providing listeners with high entertainment and copious cringe.

Segment 1: Pop Some Tags (00:03:21–00:21:49)

Main Players

• Luke: A return guest, hopeful romantic with a history in a band, has creative dating ideas (for better or worse)
• Lisa: Luke’s date, initially intrigued, later overwhelmed
• Hosts: Brooke and Jeffrey

Key Discussion Points

Luke’s Return & New Dating Strategy

• Luke is back on the show, having previously gotten into trouble for posting a photo of a date without permission.

  • "Lessons have been learned. Luke, do you know better now?" – Jeffrey (05:10)
  • "Yeah, I am better now… I’m not going to make that mistake ever." – Luke (05:03)

• This time, Luke tries a new approach:

  • Letting dates “know the real him” early so it’s “harder to ghost him.”
  • His method? Dropping hints instead of just sharing facts.

Awkward Hinting & Napkin Art

• The 'Microphone’ Doodle:

  • “I drew a picture of a microphone on a napkin.” – Luke (06:50)
  • The hosts question the tactic. Brooke suggests it can be annoying when people rely on hints instead of just being direct.
  • “The shape of that is not good.” – Brooke (07:16)
  • “Yeah, it’s a shape that can be mistaken.” – Jeffrey, alluding to an unintentional innuendo (07:18)
  • Lisa “just kind of gave me a look... but I didn’t want to blow the surprise.” – Luke

• Karaoke at Home:

  • Luke takes Lisa back to his “place” for dinner, serves food, then serenades her solo with Macklemore’s ‘Thrift Shop.’
  • “I sang The Macklemore song to her while she ate.” – Luke (09:04)
  • “Why are we even calling her? This is a train wreck.” – Jeffrey (09:11)

The Big Reveal: Parents Present!

• During the call with Lisa, a key fact surfaces:

  • “His parents were there.” – Lisa (14:51)
  • Dinner was at Luke’s parents’ place (not his own apartment as implied), and his performance was in front of them.
  • “It was set up like a kid had set it up to perform in front of his parents… a living room gospel.” – Lisa (15:15)

• Luke had left out this detail. He insists: “For the record, it is my place… I asked my parents to make dinner and have it ready.” (16:20)

• His parents clapped “louder” after his song than Lisa did (17:07).

Lisa’s Honest Feedback

• Lisa found the entire experience “super weird”—from parents attending to the relentless hints and at-home concert.
• Luke tries to salvage with: “Lisa, did you not like Macklemore?”
  • “Luke, Macklemore is not the issue. The whole date was the issue. That was weird.” – Lisa (17:43)

Notable Quotes & Moments

• "Listen, you can be a nice guy and still be a weirdo. And enough so that—no, I do not want to go out again.” – Lisa (19:14)
• Luke: “What if I play a different Macklemore song?” (19:27)

Notable Host Banter

• Jeffrey tries to defend Luke’s earnest (if deeply awkward) approach: “His tactics are a little unconventional, but that’s just what makes him so unique and special. Intentions are pure. And clearly his parents would approve.” (18:57)
• Brooke wryly challenges the premise: "Nobody has those boxes! He does napkin art. He used to be in a band." (21:27)

Timestamps & Highlights

• 05:00–07:30: Luke’s dating philosophy & napkin art
• 09:00–10:00: At-home karaoke serenade disaster
• 14:51–17:15: Lisa’s reveal—parents’ presence at date
• 18:59–19:14: Lisa’s “no thank you,” and Luke’s hopeful offer of more Macklemore

Segment 2: Love At First Flight (22:02–40:43)

Main Players

• Brad: Smitten airline passenger, recently out of a relationship (or so he claims)
• Tiffany: Brad’s seatmate and inflight connection, turned skeptical by events
• Hosts: Brooke and Jeffrey

Key Discussion Points

The Meet-Cute at 30,000 Feet

• Brad, recently single, notices an attractive woman (Tiffany) on a flight home.

• “You know when you see somebody attractive walking the plane, you’re like ‘please sit next to me, please’... Except it never happens. Except for this one time.” – Brad (24:19)

• Their seats are next to each other with an empty middle seat, which remains vacant. They hit it off:

  • “She had this cute little… snort when she laughed.” – Brad (25:52)

• Conversation is easy; Brad eventually falls asleep after getting her number and discussing future plans.

The Ghosting & The Mystery

• After the flight, Tiffany becomes less enthusiastic by text. Brad suspects something went wrong—maybe he slept weird or snored.

The Truth Comes Out: Baggage Claim (Literally)

• On the second call, Tiffany reveals:

  • While Brad slept, his phone “was blowing up… just non-stop” with messages from a woman. (34:05)
  • Tiffany glanced at the texts: “It was some girl who is just being very aggressive and texting non-stop… all caps.” (34:30)

• Brad’s version:

  • Claims he was already emotionally checked out of a six-month relationship he ended “by the time the plane landed.” (36:04)
  • “I am 100% single, and by the time the plane landed, I was 100% single as well.” – Brad (36:04)
  • Acknowledges “some loose ends I had to kind of tie up,” but asserts: “I didn’t cheat; it wasn’t a whole overlap, more like a layover.” (37:56, 38:07)

• Tiffany, put off by the drama and the mid-flight breakup, declines a second date:

  • “That will be the last time I see you sleeping. So thank you.” – Tiffany (38:27)

Notable Quotes & Moments

• “Was she your ex when you boarded the plane or was she your ex when you got off the plane?” – Jeffrey (36:37)
• Brad: “Emotionally? Yes.” (36:44)
• “That’s on the line… that’s enough to form quite the attachment on her side.” – Brooke about the ex (37:17)
• “I didn’t have two women at a time—it’s like a connecting flight. I went from one to the other.” – Brad (37:56)
• “Don’t say layover.” – Brooke, exasperated (38:08)

Timestamps & Highlights

• 24:00–27:12: Brad recounts inflight meeting and their chemistry
• 34:05: Tiffany’s reveal about the phone and endless texts
• 36:04: Brad’s explanation about his “emotional single status”
• 38:23–38:27: Tiffany firmly turns down the second date

Notable Moments & Host Energy

• Brooke and Jeffrey maintain their signature banter, often teasing both the callers and each other:
  • “I think maybe you just need to be more upfront with people.” – Brooke to Luke (17:37)
  • On Brad: “He didn’t cheat—he will dump you before he cheats on you.” – Brooke (37:40)
• Running gags about Macklemore, napkin art, and the hazards of dating in (or before) the airplane aisle.
• Memorable “awkward silences” and background giggles highlight the cringe and humor of real-world dating fails.

Best Quotes by Timestamp

| Timestamp | Speaker | Quote | |-----------|----------|-------| | 07:16 | Brooke | “The shape of that is not good.” (re: microphone drawing) | | 14:51 | Lisa | “His parents were there.” | | 17:43 | Lisa | “Luke, Macklemore is not the issue. The whole date was the issue. That was weird.” | | 19:14 | Lisa | “Listen, you can be a nice guy and still be a weirdo. And enough so that—no, I do not want to go out again.” | | 24:19 | Brad | “You know when you see somebody attractive walking the plane, you’re like ‘please sit next to me, please’… Except it never happens. Except for this one time.” | | 34:30 | Tiffany | “It was some girl who is just being very aggressive and texting non-stop… all caps.” | | 36:04 | Brad | “I am 100% single, and by the time the plane landed, I was 100% single as well.” | | 37:56 | Brad | “I didn’t have two women at a time—it’s like a connecting flight. I went from one to the other.” | | 38:27 | Tiffany | “That will be the last time I see you sleeping. So thank you.” |

Takeaways

• Authenticity matters, but so does self-awareness: Luke’s attempts to be quirky and “real” come off as confusing—and maybe a little misleading—especially when key info (like living with your parents) is omitted.
• Timing is everything: Brad found “love at first flight,” but emotional baggage and unfinished business grounded his chances.
• Hosts’ supportive, self-deprecating banter keeps the tone light, highlighting the universal truth of dating mishaps.
• Success rate for second dates: As always, exceptionally low—“low success rate, high entertainment for the rest of us.”

For New Listeners

• This episode is a perfect showcase of what “Second Date Update” does best: it combines real dating drama with humor, empathy, and a dash of schadenfreude for an audience that relates to the joy and the chaos of modern romance.

Listen for:

• Hilarious banter about napkin drawings and karaoke
• Behind-the-scenes view into accidental double-dating
• Cautionary tales about creative “reveals” and multi-tasking during mid-flight breakups

Full episodes and other “Second Date Updates” available at:

• iHeartRadio
• Apple Podcasts
• Spotify