Second Date Update: "First Timers Club"

Podcast: Brooke and Jeffrey: Second Date Update
Air Date: January 21, 2026
Hosts: Brooke & Jeffrey
Guest: Sam (Listener seeking second date)
'Second' Person Called: Witty

Episode Overview

In this entertaining and slightly awkward episode of Second Date Update, Brooke & Jeffrey help Sam, a 25-year-old who just went on his first ever date. Sam reached out because, after his big step into dating with Witty—the woman he invited out—she’s now ghosting him. The hosts get both sides of the story, uncovering misunderstandings and some truly cringeworthy first-date moments. Amused empathy and real talk remind listeners why this show is such a fan favorite.

Key Discussion Points & Insights

Introducing Sam: A “First Timer” (03:13–07:06)

• Sam’s First Date at 25

  • Sam (25) admits he's never been on a date before. His reason? Intense academic focus and shyness.
  • He met Witty while working as a graduate assistant in a university chemistry lab.
  • Witty is familiar from lab interactions where they gradually got to know each other.

• How He Asked Her Out

  • Sam asked Witty out by writing on a piece of lab paper:
    “What would you say to a cute guy in a lab coat if he wanted to take you out to dinner?”
    She said yes.
    (07:00)

The Date: Sweet Intentions, Awkward Execution (07:12–09:55)

• Spur of the Moment, No Plan

  • They went for drinks on a patio… in the cold, because Sam hadn’t thought of a spot in advance.
  • Sam asked for two blankets—but at first, kept both for himself before offering one to Witty. She declined, as he had already bundled up.

• Conversation Starters

  • They swapped “stuck-on-a-deserted-island” questions; Sam's “toilet paper” answer got some laughs—
    “What are you gonna wipe with?” (09:02 – Sam)
  • Witty played along, teasing him, but the convo included bathroom humor.

• Date Length & Ending

  • The date lasted about an hour, outside in the cold, after their workday.
  • Sam didn’t make a move (no hug or kiss), instead waiting in his car hoping Witty would initiate something.

The Aftermath: Ghosting & Recap (09:55–13:03)

• Sam saw Witty around the lab afterward, but she didn’t engage with him.
• He reveals he never explicitly said it was his first date, but hinted at having little experience.

The Call to Witty: Getting Her Side (13:23–16:28)

• Witty’s Immediate Reaction

  • "It was just like kind of a weird date. It was just a little strange. He seemed really nervous." (14:48 – Witty)
  • She confirms the chemistry lab connection and date details.

• The Date from Her Perspective

  • Conversation generally fine; Sam asked about her relationship history.
  • Witty shared she'd had two long-term boyfriends recently.
  • Sam steered the talk to traveling—specifically, a solo trip to Amsterdam.

• The "Experience" Comment

  • Witty recounts:
    “He was like, ‘I have experience.’” (15:38 – Witty)
  • She found this odd, as it was said right after she talked about boyfriends. She worries he’s alluding to, or bragging about, experience with sex workers in Amsterdam.
  • “I was like, are you like some pervert that just goes to, like, different red light districts…?” (15:52 – Witty)

The Reveal: Sam Explains Himself (16:28–20:03)

• Sam Joins the Call

  • Sam tries to clarify: He did visit Amsterdam’s red light district but says it’s just “part of the experience.”
    “I went through… I was there. That’s part of the experience.” (17:05 – Sam)
  • He claims he wanted to show he had some experience since Witty had more dating history.

• Witty’s Reaction

  • Witty is scandalized:
    “I’m totally weirded out by you comparing, like, relationships with meeting up with sex workers… just very odd…” (17:37 – Witty)
  • Sam, in an awkward pivot, confesses it was his first date ever, as he’d previously focused on studies.

• Red Flags

  • "To me, that's a red flag." (18:34 – Witty)
  • "It's red lights and red flags." (18:44 – Witty; playful yet pointed)

• Advice from the Hosts

  • Hosts (Brooke & Jeffrey) try to coach Sam about not discussing red light districts or intimate experiences from travel as “dating experience.”

Memorable Quotes & Moments

• On the Double Blankets:
  “So you guys sat on the patio in the cold?” (07:40 – Brooke)
  "I ended up with two big blankets around me..." (07:55 – Sam)

• First-date nerves:
  "I was just nervous and I was not thinking straight." (08:19 – Sam)

• Toilet Paper Logic:
  “Well sure, you couldn’t eat anything, but what are you gonna wipe with?” (09:08 – Sam)

• On Sex Worker ‘Experience’:
  “He was like, ‘I have experience.’ …Like, in, like, these places...” (15:38 – Witty, paraphrasing Sam)

• Witty's Take:
  “I just can’t believe that you’ve gone this far without ever going on a single date. To me, that’s a red flag.” (18:34 – Witty)

Resolution: Second Date? (20:04–21:58)

• No Second Date for Sam
  • Witty adamantly declines another date:
    "No, absolutely not. In fact, like, you shouldn't ask out anyone in the lab." (20:08 – Witty)
• Witty reveals she's now letting others in the lab know about Sam's odd behavior.
• Sam, awkward but defiant:
  “That's fine with me. I'm… you know, I'm actually kind of proud of it.” (20:23 – Sam)

Show Wrap-up: Learning the Hard Way (22:32–23:38)

• Hosts’ Reflection:

  • Jeffrey: “Maybe Sam wasn’t quite ready for his first date, but he was definitely ready for his second, if you know what I mean.” (22:32)
  • Hosts tease Sam’s “plenty of experience” in Amsterdam, but point out the crucial lesson:
    Don’t show off the wrong kind of “experience” or confuse types of intimacy and dating.

• Final Sentiment from Brooke:

  • “Is that something you have to learn? Isn’t this common sense?” (23:18 – Brooke)
  • Recurring theme: You learn about dating by actually doing it (and making mistakes), but not all lessons are painless.

Notable Quotes with Timestamps

• “This is the first date I’ve ever been on.”
  — Sam (05:30)

• “I just can't believe that you've gone this far without ever going on a single date. To me, that's a red flag.”
  — Witty (18:34)

• “It's red lights and red flags.”
  — Witty (18:44)

• “No, absolutely not. In fact, like, you shouldn't ask out anyone in the lab.”
  — Witty (20:08)

• “Maybe Sam wasn’t quite ready for his first date, but he was definitely ready for his second, if you know what I mean.”
  — Jeffrey (22:32)

Episode Highlights (with Timestamps)

• [05:30] Sam admits it’s his very first date ever.
• [07:40] Date location mishap, patio in the cold—a double-blanket situation.
• [09:02] Desert island question leads to “toilet paper” debate.
• [14:48] Witty describes the date as “kind of a weird date... a little strange.”
• [15:38] Witty, confused, parrots Sam’s odd “I have experience” comment.
• [17:05] Sam admits his “experience” is from Amsterdam’s red light district.
• [18:34/18:44] Witty calls “never dated at 25” a red flag; “red lights and red flags.”
• [20:08] Witty refuses a second date, tells him not to date in the lab.
• [22:32] Jeffrey’s tongue-in-cheek wrap-up about Sam’s “experience.”

Tone:
Lighthearted, awkward, and playful with genuine attempts at advice. The hosts remain encouraging to Sam, even as his inexperience and odd bragging unravel the date.

Takeaway

This episode is a classic Second Date Update—cringe-worthy, funny, and a reminder that first dates (especially your literal first) can go very wrong for innocent reasons. Sam’s earnestness and lack of filter led to misunderstanding, and Witty’s perspective highlighted the importance of social cues and TMI boundaries. No love connection, but plenty of laughs—and probably a few lessons learned for Sam and listeners alike!