Podcast Summary: Brooke and Jeffrey – Second Date Update: "Dutch Isn't Just A Language"

Release Date: September 26, 2025
Hosts: Brooke, Jeffrey, Alexis (with guest Jake and Kim)

Episode Overview

This episode centers on another classic “Second Date Update”—where hosts help a listener figure out why a promising first date didn’t lead to a second. Today’s story involves Jake, who enjoyed a quirky first date with Kim, but now Kim is acting distant, and he’s clueless as to why. The episode takes a comedic turn around discussions of going Dutch, Venmo histories, and modern dating red flags.

Key Discussion Points & Insights

1. Setting the Scene: Jake and Kim’s First Date

• Meeting and Connection:

  • Jake and Kim met through mutual friends at a rooftop birthday party and bonded over their mutual dislike for the poor music choices.
    • "We really bonded over the fact that the music was absolutely horrible." (Jake, 05:18)
  • Their mutual gripes led Jake to ask Kim out to a swanky new wine bar.

• The Date Night:

  • The wine bar also had “bad music,” which continued as a running joke and conversational crutch.
    • "We vibe talking. And again, the music was really bad, so..." (Jake, 06:26)
  • Kim and Jake swapped embarrassing stories:
    • Kim shared she froze on a game show.
    • Jake jokingly dodged sharing a real story.
      • "You just did a cop out." (Alexis, 07:29)
      • "It was a joke… I was trying to be funny." (Jake, 07:39)

• Going Dutch:

  • At the end of the night, Kim insisted on splitting the bill via Venmo, which Jake accepted.
    • "She immediately asked for my Venmo ... Maybe she's had bad dates where a guy expected something." (Jake, 08:03)

• Aftermath:

  • Kim responded to Jake's texts, but her replies felt obligatory, not enthusiastic.
    • "I can tell that, like, she's kind of just answering because she feels obligated." (Jake, 09:02)

2. The Reveal: Kim’s Side & Venmo Red Flags

• Initial Reaction:

  • The hosts call Kim. She’s familiar with the show and guesses why she’s being contacted.
    • "I've heard your show before." (Kim, 12:09)

• Kim's Perspective:

  • Kim says the date was one of the nicest she’s had in a while, but then reveals why she lost interest.
    • "It was like one of the nicer dates I've been on in a while." (Kim, 13:09)

• Venmo Investigation:

  • When Kim paid Jake on Venmo, she noticed his public payment history—a string of transactions with various women, each annotated with flirty emojis.
    • "Trish has a kissy face, Brittany has a dress emoji, Lisa has a gift box..." (Kim, 14:07)
    • "He's giving out money to a bunch of women." (Alexis, 14:44)

• Kim’s Suspicion:

  • Kim concludes Jake might be a “sugar daddy” or is at least someone dating (and paying) multiple women. She’s not interested in being part of that scene.
    • "I'm not into guys just dating multiple people at the same time." (Kim, 15:03)
    • "In the last month, it's just a ton of women... to me that makes a ton of red flags." (Kim, 15:09)

3. The confrontation: Jake Explains the Venmo Payments

• Jake’s Defense:

  • Jake admits sending women money via Venmo, but says he does it to offset their pre-date expenses or as part of the evening.

    • "I bail out. I see a lot of ladies and I pay." (Jake, 16:12)
    • "Sometimes I'll pay for the pre-dinner or whatever it cost." (Jake, 16:22)

  • He tries to normalize reimbursing women for their date preparations, and challenges Kim:

    • "Have you never said, 'oh, it cost me X amount to get ready for you?'" (Jake, 16:33)

• Kim’s Reaction:

  • Kim playfully suggests Jake should also reimburse her for her $90 in makeup and prep.
    • "If you're paying for girls' things, then why not my foundation? My Mascara concealer cost $90." (Kim, 17:06)

4. The Outcome: Will There Be a Second Date?

• Hosts' Offer:

  • Brooke and Jeffrey offer to pay for a second date if Kim agrees.
    • "We would like to offer to send you and Jake on another date. If you say yes, we will pay for it." (Jeffrey, 18:31)

• Kim’s Final Answer:

  • Kim says yes to the Venmo reimbursement but declines a second date.
    • "I'm gonna say yes on the Venmo payment. No on the second date." (Kim, 18:56)
    • Jake agrees to pay her anyway: "Yeah, I'm gonna send it. I said I would send it." (Jake, 19:12)

• Hosts’ and Jake’s Reflections:

  • The hosts joke about Jake's generosity possibly attracting more payment requests than dates.
    • "Are you going to really send it? Have a date with her?" (Brooke, 19:07)
    • "Sounds like you met your match, Jake." (Alexis, 19:09)

Notable Quotes & Memorable Moments

• On going Dutch:

  • "She immediately asked for my Venmo." (Jake, 08:03)

• On Venmo snooping:

  • "It was diabolical... Trish has a kissy face... Brittany has a dress emoji... a ton of women. To me that makes a ton of red flags." (Kim, 14:07–15:09)

• On Jake’s motivations:

  • "I bail out. I see a lot of ladies and I pay." (Jake, 16:12)

• Kim’s business-minded close:

  • "I'm gonna say yes on the Venmo payment. No on the second date." (Kim, 18:56)

• The hosts on Jake’s “charity”:

  • "Let him spoil people. Only with hot women..." (Brooke and Alexis, 21:58–22:02)

Timestamps for Key Segments

• [03:55] – Jake tells his side of the story
• [08:03] – The going Dutch moment
• [12:43] – Kim answers call, reveals her perspective
• [14:07] – Kim details Jake’s suspicious Venmo history
• [15:41] – Jake explains “paying out” to women, defends his actions
• [16:57] – Kim argues for her own reimbursement
• [18:56] – Kim declines second date, accepts Venmo payment

The Tone & Takeaway

True to Brooke and Jeffrey’s style, the episode is full of playful banter, snarky commentary, and a willingness to call out cringe-worthy dating behavior on both sides. The unresolved tension between modern independence and the shadow of “sugar daddy” culture is played for laughs, but also points to the complications of digital-age dating.

Fans of the show will appreciate Alexis’ sarcasm, Brooke’s straight talk, and Jeffrey’s attempts to instigate drama—plus the running jokes about “Reach for the Sky,” bad music, and Alexis’ own “forbidden fruit” (her brother Jake’s name).

In Short:
Kim’s Venmo snooping turned up enough red flags for her to take the money and (literally) run, passing on romance with Jake—who’s left, hilariously, still unfazed and still open to “spreading joy” via his Venmo account.

This summary skips advertisements and peripheral banter, focusing on the episode’s main story and comedic highlights.