Podcast Summary: Brooke and Jeffrey – Second Date Update Classics: Sweet Sixteen Dates + Be Excellent & Be Thirsty
Date: January 31, 2026
Hosts: Brooke & Jeffrey
Episode Type: Second Date Update Classics
Overview
This episode is a double-feature of classic “Second Date Update” segments, a fan-favorite where the hosts help listeners reconnect—or at least get closure—after being ghosted following a first date. As always, the show’s tone is playful, sarcastic, and unruly, with plenty of comedic banter between hosts and guests. The episode spotlights two memorable scenarios:
- Sweet Sixteen Dates – Kelly recounts her year of dating misadventures and frustrations when her latest prospect, Steve, goes radio-silent after a messy Cuban sandwich picnic.
- Be Excellent & Be Thirsty – Bobby (aka “Steve”) tries to woo Tori by living out a “Be Excellent” philosophy, but fails to make her feel special amidst his grandstanding good deeds.
Key Discussion Points & Insights
Fan Appreciation and Banter ([03:12])
- Brooke reads fan comments, joking about a listener who’s listened to every Second Date Update.
- Brooke (03:14): “Yikes. That is an early morning ... and you got 17 year olds now that you’re taking care of. I’m kidding ... she’s just been doing it for 17 years.”
Segment 1: Sweet Sixteen Dates (Kelly & Steve)
[04:22–20:47]
Kelly’s “Dating Wrapped” Recap
- Kelly summarizes her dating year—16 first dates with a diverse crowd (including “an Irish guy” and “one who may have been homeless”).
- Of those, only three made it to a third date; one blocked her, which she suspects was because the guy was married.
- Kelly (06:16): “It was 16 first dates total… eight were like mutual ghostings; three I rejected; and one blocked me, but he was a little sus.”
Memorable Quotes:
- Brooke (08:00): “You’re not old fashioned, you’re cheap. Let’s be honest.”
- Jeffrey (07:46): “1 in 16 being blocked, that’s not bad!”
The First Date with Steve
- Casual date: Cuban sandwich picnic at a park near a playground.
- Kelly gets sauce all over her face; Steve points it out playfully.
- Light joking about messy eating and women “making anything a positive.”
- Kelly (09:37): “[Steve] pointed to my entire lower half…‘everywhere, under your nose.’”
- Brooke (09:44): “Honestly, I didn’t realize I carried so much food on my face until I met [my husband].”
“Weird” Interaction & Potential Red Flag
- Kelly jokes about having all the kids on the playground as their children and even invents backstories—like putting a misbehaving one “up for adoption.”
- Turns awkward, later revealed as the main issue for Steve.
Memorable Quotes:
- Brooke (15:23): “So she was describing a nightmare, right? Like, that’s how she meant it?”
- Steve (15:36): “I’ve known you for like 20 minutes, and now we’re having eight kids together…”
On-Air Confrontation
- Kelly is offended that Steve thought she was serious, calls him “emotionally and intellectually stunted,” and criticizes his planning.
- Steve stands his ground, feeling attacked, and ultimately wants nothing more to do with Kelly.
Exchanges:
- Kelly (16:55): “Now I realize why I had 16 unsuccessful dates last year. It’s because they were all like you, Steve.”
- Steve (20:13): “No, I’m not going out with her again ... this woman is a little out there for me.”
Important Timestamps
- [06:09] Kelly’s “dating wrapped” breakdown
- [08:24] Introduction of Steve
- [09:37] Messy sandwich incident
- [15:07] Playground/kids conversation & Steve’s discomfort
- [16:44] Kelly confronts Steve live on air
- [18:31] End of second date prospect
Segment 2: Be Excellent & Be Thirsty (Bobby/Steve & Tori)
[25:15–41:46]
The “Tao of Steve” Philosophy
- Bobby describes his guiding rules:
- Be desireless
- Be excellent
- Be gone
- He tries to impress Tori by doing good deeds throughout the date, e.g., walking a lost tourist family to a museum, paying someone else’s unpaid restaurant bill.
Memorable Quotes:
- Jeffrey (25:38): “If you can live by all three of those rules as a man, you will become irresistible to any woman on Earth.”
Where It Goes Wrong
- Tori feels ignored and like Bobby is “on a date with everyone but her.”
- He doesn’t compliment her, leaves her waiting for a table, interrupts her stories, and is “too nice” to strangers while inattentive to her.
Exchanges:
- Tori (34:40): “It kind of just felt like I was on a date with someone who was giving attention to everyone and everything else except me.”
- Brooke (35:00): “If she’s in heels, it’s not comfortable to walk people to the–”
Confrontation and Self-Reflection
- Once prompted, Bobby explains he was trying to “demonstrate value” by being excellent to others.
- Tori just wanted normal conversation, attention, and compliments.
Exchanges:
- Brooke (39:10): “All you have to do is ask me questions and listen and compliment.”
- Bobby (41:00): “Yeah, I’m listening now. Look, you’re hot. And I’ll pick up your napkin and, like, you want me to ask you questions…what are you doing next Friday? Let’s get dinner.”
- Tori (41:16): “I’m gonna pass.”
Hosts’ Closing Reflections
- Brooke and Jeffrey riff on the madness of dating “strategies” and the overthinking that sabotages basic connection.
- Jeffrey (43:43): “Sometimes men don’t listen very good.”
Notable/Memorable Moments
- Dating "Wrapped": The opening conversation riffs on the “Spotify Wrapped” trend, setting up the first segment’s tone.
- Communication Clash: Both segments revolve around mismatched expectations and misread signs—theme: it’s easy to overthink or misinterpret in early dating.
- Playground Kids Bit: The “let’s imagine these are our kids” line, misunderstood by Steve, becomes a classic Second Date Update moment of lost-in-translation awkwardness.
Key Quotes (with Timestamps & Attribution)
- “You’re not old fashioned, you’re cheap. Let’s be honest.” – Brooke (08:00)
- “It was 16 first dates total... eight were like mutual ghostings; three I rejected; and one blocked me, but he was a little sus.” – Kelly (06:16)
- “I’ve known you for like 20 minutes, and now we’re having eight kids together…” – Steve (15:36)
- “Now I realize why I had 16 unsuccessful dates last year. It’s because they were all like you, Steve.” – Kelly (16:55)
- “It kind of just felt like I was on a date with someone who was giving attention to everyone and everything else except me.” – Tori (34:40)
- “All you have to do is ask me questions and listen and compliment.” – Tori (39:04)
- “What is Brooke saying, Jose? I don’t know.” – Jeffrey (44:11)
Important Segment Timestamps
| Segment | Timestamp | Description | |------------------------|------------|-------------------------------------------------| | Fan Mail & Banter | 03:12 | Brooke reads testimonial, pokes fun at fandom | | Kelly’s Dating Recap | 06:09 | “Dating wrapped” breakdown | | Messy Sandwich Story | 09:37 | The sandwich-on-face incident | | Playground Kids Bit | 15:07 | "Imagine if we had that many kids" awkwardness | | Confrontation | 16:44 | Kelly and Steve face off live | | Tao of Steve Intro | 25:38 | Bobby’s dating rules explained | | Good Deeds Date | 28:07 | Museum & restaurant heroics | | Tori’s Side | 34:40 | Tori: “On a date with everyone but me” | | Bobby’s Philosophy | 38:02 | Overthinking leads to failed connection | | Final Outcomes | 20:13,41:16| Both women reject second dates |
Tone & Takeaways
- Original Speaker Style: Banter-heavy, frequently sarcastic, with a blend of empathy and irreverence.
- Themes:
- Modern dating is increasingly complicated by overanalysis and self-sabotage.
- Communication—especially humor and intentions—easily gets lost or misinterpreted.
- Sometimes, elaborate strategies work against genuine connection.
- Memorable Moments: “Let's imagine if we had that many kids” gone awry; the “be excellent” philosophy takes center stage before crashing and burning under the weight of its own rules.
In Summary
This classic episode of Brooke and Jeffrey’s Second Date Update highlights the pitfalls of modern dating. Between Kelly’s streak of disastrous first dates and Bobby’s over-engineered attempts to “be excellent,” the show delivers both cringe and comedy in equal measure. The core message? The best dating advice might be to put away the playbook, be present, and leave the grandstanding for another day.
For listeners: If you’ve ever tried too hard or said something that came out all wrong on a first date, you’ll find plenty to relate to—and laugh about—here.