Brooke and Jeffrey: Second Date Update Classics
Episode: Scam the Scammer + V-Day Pass Out
Date: February 14, 2026
Episode Overview
This Valentine’s Day special revisits two classic, high-drama Second Date Updates. As always, the premise is simple: a listener has been ghosted after a first date—they contact the show to uncover the true reason why, with the possibility (however unlikely) of scoring a second date. In both segments, the “why” veers into outrageous territory, highlighting messy miscommunications, bad dating behavior, and the hosts’ signature blend of empathy and sharp wit.
Segments Covered:
- Scam the Scammer — A vengeful listener wants answers and revenge after being ditched mid-date.
- V-Day Pass Out — A Valentine’s date ends in the ER, but the real drama comes later when secrets unravel.
Segment One: Scam the Scammer
Introduction and Setup – [03:08 – 04:38]
- Brooke kicks off "Galentine's Day" in the studio, promising that revisiting bad dates will make everyone feel better about their own love lives.
- Jeffrey sets up the “classic” they’ll be replaying: one “very angry” woman wants not just answers but revenge for being left in the most embarrassing way imaginable on her date.
- Jeffrey teases: “There’s a scamming coward on the dating apps, and you need to help me expose him.” [04:42]
The Story (Lindsay’s Side) – [05:23 – 07:42]
- Lindsay’s Complaint: She met Alex on a dating app, they had dinner, and he seemed “more into me than I was into him.”
- Towards the end of the meal, Alex excused himself to use the bathroom—and never came back. Lindsay was left sitting alone, humiliated. (“It was humiliating. I felt like an idiot.” — Lindsay, [06:22])
- She waited 15-20 minutes before asking the waiter to check for him. He had vanished.
- Lindsay says she tried “nice” texts first, but when Alex didn’t reply, her tone shifted: “He doesn’t deserve me being nice.” [08:23]
- Aim: Lindsay has zero interest in reconciling; she wants to understand why he left and “humiliate him on the radio.” [09:26]
Hosts Discuss – [08:33 – 12:01]
- The team debates possible explanations—could there be a valid reason? (Brooke: “We have heard where people have had, like, bathroom emergencies where they can’t go back to the table.” [07:57])
- Jeffrey quips, “There is no good reason a man should ever do that to a woman.” [07:52]
Confronting Alex – [12:13 – 17:02]
- Alex answers the call, quickly admits to ghosting Lindsay mid-dinner: “I take full credit for that.” [13:22]
- His Reason: Before their date, Alex saw Lindsay rehearsing with her friend how to fake an app error so Alex would pay for her Uber home. He says, “She was practicing that her Uber wasn’t working. She can totally afford it. She just wants to make a fool out of somebody.” [17:12]
- Lindsay’s Defense: She claims wanting help to get home safely after drinks is normal, and that Alex’s reaction was overkill.
- Tense, overlapping arguments ensue. Lindsay says, “So your answer to that was to get up and just leave dinner at the end and leave me the bill? Like, like an immature loser?” [15:33]
- Alex admits: He knowingly ordered the most expensive menu item before leaving, to “scam the scammer.” [16:23]
- Host Commentary: “You guys are both a little bit of manipulators.” — Jeffrey [16:33]
Key Memorable Quotes
- Lindsay: “If he’s going to humiliate me, I’m going to humiliate him on the radio.” [09:26]
- Alex: “I only scam the scammer. I was ready to have a genuine date with her.” [16:37]
- Brooke: “You got caught, girl. You got caught scamming him for an Uber ride.” [17:33]
Ending & Takeaways – [18:22 – 19:29]
- No second date is offered. Both parties double down on their view of the other as manipulative.
- Humiliation seems mutual by the end, and the hosts sum it up as a cautionary (yet hilarious) tale.
- Brooke’s Sarcastic Take: “Thank God. You are such a champion of women, Jeffrey.” [19:36]
Segment Two: V-Day Pass Out
Setup and Reese’s Story – [23:44 – 29:19]
- Reese went on a pre-Valentine’s Day date with Jen after a recent breakup. They chose a bar with an “all things pink” theme.
- Reese is diabetic; Jen doesn’t know. When she orders them both sugary pink daiquiris, Reese figures he can manage with one—but suffers a diabetic episode.
- “There was a moment where I couldn’t really talk, and I wrote on a napkin and slid it to Jen—it said ‘hospital.’” — Reese [27:40]
- Jen, confused and frightened, ends up driving him to the hospital. He comes to later, alone, and texts her apologies—she replies once, but goes silent afterward.
Host Speculation and Empathy – [29:19 – 31:47]
- The hosts discuss how traumatizing the situation must have been for Jen: “If this girl isn’t calling you back because it freaked her out, that is somewhat understandable. But once she talks to you, she’ll have a lot of empathy for you.” — Brooke [30:39]
- Reese isn’t so sure her ghosting is just about the medical emergency.
Jen’s Perspective and The Twist – [31:45 – 36:35]
- Jen answers the call cordially.
- She clarifies: “It literally has nothing to do with that. I don’t hate people who have diabetes. I hate people who already have girlfriends.” [33:18]
- The Reveal: At the hospital, another woman arrived, claiming to be Reese’s girlfriend and his emergency contact. The hospital let her in to see him.
- Hosts scramble for explanations: Could it be an ex? Outdated contact information?
Reese’s Confession
- Upon being confronted, Reese finally admits: “Yes, I am in a relationship, but I’m not happy, and I want to see what was out there.” [36:18]
- The hosts and Jen react with disbelief and disgust.
- Jen shuts it down: “You got a free ambulance ride. Let’s just chalk it up to that, okay? You got lucky.” [37:03]
Key Memorable Quotes
- Jen: “I hate people who already have girlfriends.” [33:18]
- Reese: “Yes, I am in a relationship—but I’m not happy, and I want to see what was out there.” [36:18]
- Brooke: “This is very messy, very sloppy, sloppy work.” [36:12]
- Jen: “It’s a not a no, it’s a hell no.” [38:17]
Ending and Lessons – [40:01 – End]
- The hosts reflect on how manipulative or dishonest people can sound plausible—even charming—until details unravel.
- Brooke sums up the feelings in the room: “Do not aspire to be this dude.” [40:59]
Notable Quotes & Timestamps
- “If he’s going to humiliate me, I’m going to humiliate him on the radio.” — Lindsay, [09:26]
- “She was practicing that her Uber wasn’t working … she just wants to make a fool out of somebody.” — Alex, [17:12]
- “You got caught, girl. You got caught scamming him for an Uber ride.” — Brooke, [17:33]
- “There was a moment where I couldn’t really talk, and I wrote on a napkin and slid it to Jen—it said ‘hospital.’” — Reese, [27:40]
- “Yes, I am in a relationship, but I’m not happy, and I want to see what was out there.” — Reese, [36:18]
- “It’s a not a no, it’s a hell no.” — Jen, [38:17]
- “Do not aspire to be this dude.” — Brooke, [40:59]
Episode Takeaways
- Scam the Scammer is less about romance and more about mutual manipulation and public callouts—both parties come off badly, and both feel exposed.
- V-Day Pass Out initially appears to be about a medical emergency, but quickly pivots to an even bigger betrayal—dating while in a relationship, exposed by an unexpected hospital visitor.
- The hosts balance humor, empathy, and tough love as they probe for the truth, tease each other, and celebrate the disaster for its entertainment value.
- Ultimately, both cases serve as cautionary tales for the daters and comedic gold for listeners.
Key Timestamps
| Time | Segment/Moment | |-----------|----------------------------------------------------------| | 03:08 | Start of Galentine's Day episode and setup | | 05:23 | Lindsay retells her “scammer” story | | 12:13 | Calling and confronting Alex | | 15:38 | Lindsay vs. Alex argument peaks | | 17:33 | Brooke calls out Lindsay’s Uber scam | | 23:44 | Host intro to V-Day Pass Out/recount of Reese’s story | | 27:40 | Reese’s diabetic episode described | | 33:18 | Jen’s bombshell: “I hate people who already have girlfriends” | | 36:18 | Reese’s confession: he has a girlfriend | | 38:17 | Jen’s absolute NO to another date | | 40:59 | Brooke: “Do not aspire to be this dude.” |
Tone and Style
This episode is a rollercoaster of confrontational and comedic moments, with the hosts leaning into sarcasm, supportive jabs, and exasperated laughter. Both stories unfold with dramatic reveals, heated arguments, and the kind of raw honesty that is at once shocking and addictively entertaining.
For anyone who’s never heard Brooke and Jeffrey’s Second Date Update, this Valentine’s episode is a perfect crash course in why the series is both beloved and notorious: It’s messy, relatable, and endlessly funny—often at the daters’ expense.