Brooke and Jeffrey: Second Date Update Classics

Episode: "Driving Miss Laurie" + "Lick My Neck"
Air Date: November 29, 2025
Host: iHeartPodcasts

Episode Overview

This classic installment of "Second Date Update" features two memorable misadventures in modern dating: "Driving Miss Laurie" and "Lick My Neck." In typical Brooke and Jeffrey fashion, the hosts inject humor and empathy as they dig into two "ghosted" first-date stories—each revealing the awkward, unexpected, and sometimes utterly bizarre realities of finding love (or at least a second date) in the app era.

The episode’s main theme is the unpredictable gap between dating expectations and reality—from age gaps to misread intentions, to “signature moves” that might turn out to be notorious.

Segment 1: "Driving Miss Laurie"

[03:09-19:52]

Main Discussion Points

• Nate’s Story:

  • Nate, a 32-year-old valet, seeks advice after a date with 49-year-old, successful businesswoman Laurie.
  • He decided to expand his dating prospects to older women after getting bored with those his own age.

• Date Details:

  • Laurie picked the restaurant and insisted on paying.
  • They found unexpected common ground: video games, specifically Rocket League.
  • The date ended with Laurie giving Nate a kiss—on the forehead—which the hosts (and Nate) found ambiguous.

• Post-Date & Ghosting:

  • Laurie invited Nate to meet her one afternoon at 2 pm for a potential second meeting, but the timing clashed with Nate’s work.
  • Attempts to arrange another date fizzled, with Laurie increasingly elusive.

Notable Quotes & Moments

• On dating older:
  • Jeffrey: “Dating older women, it’s like adult braces. You’re going to get to a point where it’s… good for me, but also gonna be weird because everyone around me is gonna see me.” [04:00]
• The forehead kiss:
  • Alexis: (laughing) “Oh, oh, oh. If she thinks of him as like a…” [08:46]
  • Jeffrey: “Back in the day, you started with a forehead kiss… There were way more bases back in the day.” [08:53]

The Reveal

• The Truth Comes Out:

  • Laurie reveals she’s actually married and only joined the app to find a valet to teach her stepson how to park (she found Nate’s valet profession promising).
    • Lori: “I guess my intentions for wanting to meet up with him… I’m married.” [14:30]
  • Further reveals their dinner was more of a job interview for this "driving instructor" role.
    • “I bought you dinner. It wasn’t a date. I didn’t want you to think it was a date. It was sort of an interview.” [16:52]
  • Laurie had marked “looking for friendship” on her profile, but admits she wasn’t explicit about her real motives.

• Nate’s Reaction:

  • Nate is shocked, embarrassed, but ultimately practical.
    • “I’ll take money over forehead kisses any day.” [18:59]

Outcome

• The hosts propose that Nate take the gig training Laurie’s son, in exchange for some business mentorship from Laurie—a classic Second Date Update, where the only successful match is business, not romance.

Segment 2: "Lick My Neck"

[23:41-39:20]

Main Discussion Points

• Eric’s Story:

  • Eric, armed with a wacky dating app profile and a sense of humor, recounts a recent date with Dana.
    • Eric claims to have been a “disgraced Russian submarine captain” (in jest). [24:14]
  • The conversation with Dana was easy; they bonded over travel photos and mutual interests.

• The Date & The Move:

  • Dana traveled more than halfway across the city to meet Eric.
  • Date went well; after an enjoyable dinner, as Dana turned around, Eric spontaneously kissed the back of her neck.
    • Eric: “And the back of her bare neck was in front of me. And I just couldn’t help it. I bent down and I gave her a kiss on the neck.” [28:17]

• The Aftermath:

  • Dana smiled and, according to Eric, things got “slightly more intimate” afterwards.
  • Despite this, Dana cut off contact after the date.

Notable Quotes & Moments

• About the neck kiss:

  • Alexis: “That just made me, like, flinch.” [28:30]
  • Brooke: “The more you describe your kissing, the less I like the tender neck kiss.” [29:42]
  • Alexis, joking: “Lick my neck.” [29:18]

• Host banter and mock demonstration:

  • The hosts recreate the moment in the studio, with Brooke attempting to neck-kiss Alexis—eliciting horror and laughter. [30:12-31:40]

The Reveal

• Dana’s Perspective:
  • Dana appreciated Eric's confidence, but his "experienced" vibe made him seem like a "gigolo." [34:13]
  • She posted a picture of his profile in the Facebook group “Are We Dating the Same Guy?” to see if others had crossed paths with Eric.
  • Three women replied saying Eric had the same signature “back of the neck” kiss move with them.
    • Dana: "It was honestly so weird and so creepy, and it's like, this is his calling card." [35:53]
  • Eric had previously claimed to the hosts this was the first and only time he'd used the move.

Outcome

• Dana rejects the offer of a second date, calling Eric a "creepy and a liar."
  • “But once you got on and denied that other girls said that, now you’re just a creepy and a liar.” [38:41]
• The hosts mockingly suggest Eric find a new move and officially retire the back-of-the-neck kiss forever.

Final Thoughts & Memorable Takeaways

• On Dating Miscommunications:

  • The episode underscores how easily intentions and expectations can be misread—whether someone is looking for romance, a babysitter, or a driving instructor.
  • Humor and empathy from the hosts help soften the blow for the bewildered guests.

• On “Signature Moves”:

  • The cringing studio response to the “neck kiss” is memorable, as is the real-world feedback from a Facebook group connecting women’s weird date stories.
  • Collective group wisdom: retire the “sneak attack” neck kiss.

Notable Closing Quote

• Jeffrey: “Well, gentlemen, take surprise back of the neck kiss out of your Rolodex… Eric ruined it for us.” [41:07]
• Alexis: “Nobody should have a go to move. It’s weird.” [41:17]

Timestamps for Key Segments

• Introduction and Ad Banter: 00:00–03:09 (skipped)
• Driving Miss Laurie Segment Begins: 03:09
• Laurie’s Confession (Married/Job Interview): 14:30–16:59
• Segment Wrap-up and Banter: 18:57–19:52
• "Lick My Neck" (Eric’s Story) Begins: 23:41
• Eric Describes Neck Kiss: 28:16–28:25
• Hosts’ In-Studio Neck Kiss Demo: 30:12–31:40
• Dana Details Facebook “Are We Dating the Same Guy?” Group: 34:13–36:04
• Eric and Dana Confrontation: 36:39–38:47
• Debrief and Retiring the Neck Kiss: 41:07–42:06

Tone and Style

• Lighthearted, silly, and irreverent, but with real-world empathy for the guests’ (often cringe-inducing) situations.
• Hosts specialize in teasing, banter, and in-studio antics to ease the tension.
• Memorable moments include social commentary on dating "moves," generational gaps, and the ever-present ghosting phenomenon.

For New Listeners

This episode epitomizes “Second Date Update”—love attempts, laughter guaranteed. If you’re ever ghosted, just be grateful you didn’t end up as a driving tutor, or discovered your date had a “signature move” citywide.