Podcast Episode Summary

Podcast: Brooke and Jeffrey: Second Date Update
Episode: Second Date Update Classics: Rome-ANTS Isn't Dead + Standup Standoff
Date: September 13, 2025
Theme: The episode features two classic Second Date Update segments, exploring unforgettable (and sometimes awkward) first dates with follow-ups to uncover why a second date never materialized. In true "Brooke and Jeffrey" style, the hosts provide witty commentary while trying to help their listeners navigate the treacherous waters of modern dating.

Episode Overview

This episode brings together two fan-favorite segments:

1. "Rome-ANTS Isn't Dead" - A uniquely memorable, enigmatic date featuring playful riddles and unusual chemistry.
2. "Standup Standoff" - When a standup comic's date goes off-script, hilarity (and mortification) ensues.

The hosts blend humor, empathy, and honesty as they attempt to decode their listeners' romantic misadventures.

Segment 1: Rome-ANTS Isn't Dead

[04:33] – Introduction & Setting the Scene
Jeffrey: "You are about to meet one of the most unique and interesting women that we've ever had on this show ever."

• Brett's date with Taylor is described as unforgettable, mysterious, and even "hypnotizing."

Key Discussion Points

• Meeting Taylor ([06:11])
  • Brett met Taylor on a dating app; she appeared artsy, covered in paint, posing with an incredible painting.
  • He was immediately captivated, describing her as “a goddess” with a striking aura—though not his usual physical type.
• The Date ([08:13])
  • Took place at a restaurant with a deep, philosophical conversation ("talking about love and the end of time").
  • Brett admits he had trouble following some of her thinking but felt a strong connection.
  • Physical gestures were mild: dropped her off with just a kiss on the cheek ([10:26]).
• Taylor's Communication Style ([11:02])
  • Taylor spoke “mysteriously a lot." Brett liked her enigmatic way but found her hard to decode.

Memorable Quotes & Moments

• Brooke: "Did that work out for you?"
  Brett: "Not sure. You know, I did my best, but I mean, I think we had a great conversation… I don't know if I understood everything completely she was talking about." ([09:04])
• Brett on Taylor's vibe:
  "She just started a fire in me." ([11:19]) Alexis: "That's a passion feeling."
• Alexis trying to interpret Taylor's riddles:
  "French fries!" ([15:34]) when Taylor poses a love-related riddle.
• Taylor communicating through puns and riddles:
  “What do you call two Italian aunts? Rome-ANTS.” ([16:21]) Later: “It looks like some bunny loves you.” ([19:01])
• Hosts getting confounded:
  Brooke: "Can we answer a question? Just one, not another question." ([23:14])

Timestamps of Important Segments

• Brett describes how Taylor stood out: [06:27]
• Date details and philosophical conversation: [08:13]
• Taylor’s first phone interaction, love-themed riddles: [14:51]
• "Rome-ANTS" pun and more riddles: [16:21]
• Brett and Taylor finally find mutual understanding: [18:20]
• Taylor’s answer to a second date, via another riddle ("Did Adam and Eve ever have a date?"): [20:18]

Outcome

• Taylor never gives a direct answer, instead responding with, "What will be, will be." ([21:06])
• Hosts (especially Brooke) get increasingly exasperated with Taylor’s riddles, but Brett clearly vibes with her style.
• Jeffrey (sarcastically): "No wonder he reached out to us for help. I'm gonna say yes, that she agreed to go out and meet up with Brett one more time." ([21:09])

Segment 2: Standup Standoff

[25:25] – Introduction & Setting the Scene
Jeffrey: "On the phone we've got a stand up comedian."

• Darren seeks help after his date with Erin fizzled; he's unsure what went wrong.

Key Discussion Points

• Meeting Erin ([27:05])
  • Met at Darren’s stand-up show; Erin initially said she "doesn't date comics."
  • Darren tried to be clever: "That's fine because I work construction." ([27:41])
• The Date: Hop-On Hop-Off City Tour ([28:14])
  • Chose a city bus tour instead of a bar for something "classy."
  • Darren decided to get off the bus last minute as a joke, leaving Erin onboard, then pretended to chase after it.
  • Erin was not amused and was left alone on the bus for a stop ([29:19]).
• Erin's Reaction ([36:13])
  • She found the prank stressful and inappropriate for a first date, lacking enough rapport for such humor.
  • Darren apologized but the mood for the day was soured.
• Why Erin Ghosted ([37:24])
  • She admits Darren is “funnier on stage than in person," and realizes his style doesn't fit her sense of humor.

Memorable Quotes & Moments

• Darren describes the moment:
  "I thought it would be funny to get off the bus right before it left for the next stop… she was still on the bus." ([29:18])
• Erin’s critique:
  "I like to laugh and everything, but just imagine being in my shoes watching your date…being outside of a bus watching you. I mean, I was horrified..." ([35:53])
• The reveal:
  Erin started dating the bus tour guide, who asked for her number after the incident. Erin (to Darren): “While you’re honing your craft, working in a quiet room, he’s out there actually performing every day." ([39:31])
• Hosts’ reaction:
  Jeffrey: "Man, this was a big win for bus tour guides everywhere." ([42:19]) Brooke: "Dad humor is on top again." ([42:23])

Timestamps of Important Segments

• Darren describes his stand-up background: [26:17]
• Details of the first date and the bus prank: [28:14]
• Darren's confusion about Erin's lack of response: [31:13]
• Erin explains her perspective and reveals the tour guide twist: [35:53] onward
• Final reactions and wrap-up with the bus guide revelation: [39:10]
• Hosts' closing thoughts on the "bus tour guide win": [42:19]

Host & Listener Commentary

• Hosts oscillate between empathy, frustration, and laughter, especially dealing with Taylor’s cryptic personality and Darren’s comic antics gone awry.
• Running Gags:
  • Alexis and Brooke struggle to interpret Taylor’s riddles, joking about how “cheese fries” and “French fries” fit into the metaphors.
  • Jeffrey repeatedly emphasizes how unconventional and “out there” these dates are for even their show.
• Notable Listener Comment: ([03:40])
  • Lisa: “I’ve been on 63 first dates only waiting for my second date update. How have we not talked to you?”

Episode Conclusion

• The episode underscores the unpredictability of dating—ranging from poetic, enigmatic conversations that defy logic to comedic pranks that miss the mark.
• Both stories feature men out of their element, struggling to connect with women who have their own strong personalities and preferences.
• Hosts encourage listeners to submit their own dating stories for future segments, noting that even the most awkward encounters can make for good radio.

Notable Quotes & Moments (with Speaker Attribution)

• [05:07] Jeffrey: “Will you like her or will you want to drive your car into a ditch, or will you fall somewhere in the middle?”
• [15:01] Taylor: “How do French chefs make you love them?... They butter you up.”
• [16:29] Taylor: “What do you call two Italian aunts? Romance.”
• [19:01] Taylor: “It looks like some bunny loves you.”
• [37:24] Erin: “I think he's funnier on stage than he is in person... I'll just say he's not my kind of comedy.”
• [39:10] Erin: “...the tour operator really put me at ease... we've been out a couple of times, and I just don't quite feel right talking to anybody else.”
• [42:19] Jeffrey: “This was a big win for bus tour guides everywhere.”

Final Thoughts

If you like your dating stories served with equal parts cringe, charm, and zany wordplay, this episode stands out as a classic double dose. The hosts’ blend of good-natured teasing and genuine attempts to help make for highly entertaining listening—whether you’re searching for your own second date or just there for the schadenfreude.