Brooke and Jeffrey: Second Date Update Classic — “Red Flaggy Much?”
Date: November 24, 2025
Hosts: Brooke & Jeffrey, featuring show commentators/co-hosts
Guest participants: Jordy (listener seeking the second date), Harper (his recent date)
Episode Overview
In this episode of "Second Date Update," listener Jordy seeks help from Brooke & Jeffrey to understand why he was ghosted by Harper, a waitress he met and felt a connection with after a promising first date. The show dives into generational dating red flags, expectations around availability, and the games people play in modern romance—delivering both awkward laughs and candid insights into why some connections inexplicably fizzle.
Key Discussion Points & Insights
1. Setting the Scene: Real-Life Dating vs. Online Trends
- Brooke highlights that the majority of new couples now meet online, not in real life—making Jordy an outlier (“bucking all the latest trends”).
- [05:33] “Because recent studies have shown about 50% of couples now meet online compared to just 22% only five years ago.” —Brooke
- Jordy explains he met Harper at a German bar where she worked, after a friendly, responsible gesture (he asked her to cut off a drunken friend of his).
2. The First Date: From Bocce Ball to ‘Quickie Loran’
- Jordy describes his nerves and embarrassment, mispronouncing “quiche Lorraine” as “quickie Loran,” which became a lighthearted moment with Harper.
- [09:09] “I said quickie Loran. You know I didn’t take French in high school.” —Jordy
- The hosts affirm that self-deprecation and humor can be endearing on a date.
- The date ended with a kiss and a positive, enthusiastic text from Harper, who wrote she couldn’t wait to see Jordy again.
3. The Ghosting Mystery
- Ten days pass with no follow-up date secured, despite apparent mutual interest. Jordy is confused—the hosts brainstorm potential reasons (work schedule, family emergency, another romantic interest, etc.).
- [10:09] “You’ve had a solid first date. You kissed her at the end…and she’s the one saying ‘I can't wait to hang out again.’” —Brooke
4. Making the Call: Confronting Harper
- Once Harper is on the phone, she reveals her reason for pulling back:
- Jordy was “too available”—he offered her Friday, Saturday, and Sunday for their next meet-up.
- Harper shares a belief she and her friends hold: men aged 24–32 who are this open in their schedules are “losers” and unlikely to be ambitious or successful.
- [14:54] “If they have that much time to hang out, it really means that he’s a loser.” —Harper
- The hosts challenge this logic, arguing Jordy might simply be making an effort and being respectful of her schedule as a service worker:
- [15:43] “You’re a waitress…He’s probably just trying to give you options because it’s probably hard to align schedules.” —Jeffrey
- [15:56] “Because nowadays we hear from a lot of women who say guys don’t put in enough effort...Jordy sounds like the total opposite.” —Brooke
5. Red Flags, Games & Expectations
- Harper clarifies that she expects a guy who’s “grinding away, planning for his future,” not available every night. She seems to value a sense of pursuit or challenge.
- [17:08] “It just seems like he’s just wide open to do whatever, and we're trying to build who we are as people.” —Harper
- She further says her “perfect guy should never have all the time in the world for me.”
- The hosts react with sarcasm and disbelief, seeing it as an example of unnecessary dating “games.”
6. Jordy Responds: Honest Confusion
- Jordy is asked to react directly to being called “a loser who has too much time on his hands.” He’s baffled, reiterating he was only trying to show interest and that “playing games” feels childish.
- [19:35] “I just don’t understand why you want to play these games. Like, we met in real life. I thought you were a good person.” —Jordy
7. The Dealbreaker: No Second Date
- Brooke offers Harper a paid second date with Jordy; he jokes that he’s now “all booked up for a while” after the experience.
- Harper rejects, disliking what she calls the “games” Jordy is now playing by acting less available.
- [20:55] “I mean, I’m not really into these games that he’s playing with me, and I’m not gonna fall for it now.” —Harper
Memorable Quotes & Moments
On Modern Dating Double Standards
- [16:24] “He should be grinding away, planning for his future…not working or like working on a promotion...” —Harper
- [16:50] “Maybe that’s why his hygiene is so good. He’s got time for it.” —Jeffrey
On ‘Playing Games’
- [19:28] Jeffrey (joking): “Tell her you don’t want to date!”
- [20:02] Jordy: “Look, Harper, let’s rewind. Pretend I didn’t call you for two weeks. Are you turned on now?”
- [21:05] Jordy (to Harper): “Look in the mirror. Sweet.”
Host Reactions (Lighthearted and Wry)
- [19:09] “For your future, stay in your lane and keep not tipping people after they give you great service.” —Brooke
- [20:49] “Finally, he got it.” —Jeffrey, when Jordy claims to be ‘booked up’ after Harper’s critique
Timestamps for Key Segments
- [05:33] — Data on how people meet, set-up of Jordy and Harper’s meeting
- [08:11] — Jordy describes asking Harper out and their first date details
- [09:09] — Mispronouncing “quiche Lorraine”/date highlight
- [10:09-11:00] — Aftermath: first date follow-up and Jordy’s confusion
- [13:13] — Harper joins the call
- [14:54] — Harper explains the “loser” theory about availability
- [16:24] — Further justification of her red flag reasoning
- [19:35–20:00] — Jordy counters and tries to understand Harper’s logic
- [20:32–21:00] — Final offer and rejection of the second date; summarizing the disconnect
Episode Tone
- Conversational, playful, sometimes exasperated—the hosts balance gentle encouragement for Jordy with disbelief at Harper’s rigid “red flag” rules.
- The exchange is full of dry, sometimes sarcastic humor, with both empathy and sharp edges.
- The show ultimately lampoons the contradictory messages and games of modern dating, giving listeners both entertainment and a bit of catharsis.
Final Thoughts
This episode stands out for its exploration of modern dating contradictions—“effort” vs. “try-hard,” “being available” vs. “too available,” and the generational or social media-driven mindsets that turn simple courtship into a psychological labyrinth. Both hosts and guests acknowledge how confusing these rules can be, leaving listeners questioning which “red flags” truly matter.