Second Date Update: "Way Too Natural"

Podcast: Brooke and Jeffrey: Second Date Update
Episode Air Date: September 30, 2025
Host: iHeartPodcasts

Episode Overview

In this "Second Date Update" episode, Brooke, Jeffrey, Alexis, and Sydney help listener Nick uncover why he's been ghosted after what he thought was a promising first date with Sydney, a woman he met playing pickleball. The team navigates a blend of awkward humor, real talk about dating “icks,” and a few cringe-worthy revelations to get to the bottom of this romantic mystery. Expect candid admissions, a very natural first date, and playful panel banter all the way through.

Key Discussion Points & Insights

1. The Meet Cute: Pickleball Mishap

• [04:55] Nick shares how he met Sydney while playing pickleball in a mixed doubles league. He inadvertently hit her in the chest with the ball, prompting some post-game drinks with the group.
• The group (Brooke, Alexis, Jeffrey) jokes about the growing popularity of pickleball and Nick's "meet painful," not "meet cute."
• Nick and Sydney hit it off and spent extra time together at the bar, making a personal connection outside of the group.

2. Setting up the Date

• [07:12] Nick invites Sydney to a local farmer's market, claiming it's his usual routine (later revealed he had never been before!).
• The panel finds this move both cute and slightly calculated.

3. Three Hours of Bonding (Or Not?)

• [07:40] Nick describes a lengthy three-hour date: walking through the farmer's market, continuing on to a park, talking the whole time.
• He says he felt confident enough to go in for a kiss at the end, but Sydney literally ducked, leading to a hilariously awkward goodbye.

Notable Quote

• Nick:
  • "I leaned in for a kiss, and she did this, like, old-timey comedian thing where she, like, went straight down like it was an elevator."
  • [08:08]

4. Nick is Ghosted

• [09:02] It's revealed Sydney hasn't responded in a week. Nick’s convinced it must have been the failed kiss, but wishes he knew if there was more.

5. Second Date Update Call: Getting Sydney’s Side

• [11:43] The team dials Sydney, who’s surprised (and a bit baffled) to be on air.
• She reveals her version: she tried to “get out of there sooner,” feeling the ick not from conversation, but from Nick’s odd behavior at the market.

The Real Reason: "Way Too Natural"

• [13:54]–[15:36] Sydney describes Nick taking off his shoes, leaving them at a vendor stall, and walking barefoot through a city farmer’s market.
• She says he kept commenting, “I can really feel the earth right now,” despite walking on pavement.
• After retrieving his shoes, he just carried them around at the park—still barefoot.
• The real kicker:
  Nick goes to the bathroom behind a tree in the park, clearly in view and within earshot.

Notable Quotes

• Sydney:
  • "I mean, like an hour in, I was kind of ready to go." [13:14]
  • "He took his shoes off and then asked one of the people at a stall to watch them for him... and proceeded to walk the whole farmer’s market without shoes on." [13:54]
  • "He just gets up, walks over to this tree not far away from me at all, like, within eyesight—just goes to the bathroom behind the tree." [15:37]
  • "He's just a little too one with nature for me, I think." [16:25]

6. Nick Confronts the Truth

• [16:43]–[18:04] Nick comes on the line, sounding sheepish but unapologetic about his barefoot preferences.

• He explains:

  • "I really, really do not like wearing shoes when I’m outside." [17:09]
  • "I do wash my feet before I climb into bed. Just, you know." [17:22]
  • "Trees have been around longer than plumbing." (On peeing in public) [17:57]

• Sydney doubles down that the “natural” vibe just wasn’t for her.

7. Panel Reactions and Date Offer

• Brooke and Alexis try to salvage the situation by offering to pay for a second date. Brooke even pitches the possibility of Nick “maybe” wearing shoes next time.

• Sydney politely declines, reaffirming that they’re just very different people.

• Nick seems remarkably unfazed:

  • “You know, I actually feel pretty okay about all of this.” [19:21]

8. Memorable Moments & Panel Banter

• The team cracks up about the bizarre “elevator duck” to dodge a kiss, with Alexis marveling at Sydney’s reflexes.
• Panel sums up key dating lessons: keep your shoes on, use public restrooms, don’t pee on a slope when barefoot—bonus survival show idea.

Memorable Quotes & Moments with Timestamps

• Nick on the failed kiss:

  • "I leaned in for a kiss, and she did this, like, old-timey comedian thing where she, like, went straight down like it was an elevator." – Nick ([08:08])

• Sydney on the barefoot walk:

  • "He took his shoes off and then asked one of the people at a stall to watch them for him... and proceeded to walk the whole farmer’s market without shoes on." – Sydney ([13:54])

• Sydney on the clincher:

  • "He just gets up, walks over to this tree not far away from me at all... just goes to the bathroom behind the tree." – Sydney ([15:37])

• Nick’s shoes-are-optional philosophy:

  • "I really, really do not like wearing shoes when I’m outside." – Nick ([17:09])

• Panel on the moral of the story:

  • "Add all those to your friends’ first date checklist: Show up on time, tip your waiters, keep your shoes on, don’t pee on trees." – Brooke ([22:44])

Important Timestamps

• [04:55] – Nick describes meeting Sydney on the pickleball court.
• [07:12] – Farmer’s market date setup.
• [08:08] – The failed kiss (Sydney’s “elevator duck”).
• [09:02] – Ghosting and Nick’s confusion.
• [11:43] – Team calls Sydney for a “second date update.”
• [13:54] – Sydney reveals Nick’s barefoot behavior.
• [15:37] – Public urination story.
• [16:43] – Nick responds.
• [19:21] – Sydney declines a second date; Nick is content.
• [22:44] – Brooke’s “first date checklist” for listeners.

Episode Takeaway

This episode delivers on oddball “icks” and unexpected dating dealbreakers. What started as a classic meet-cute at pickleball turned into an “au naturel” saga of barefoot market walks and poorly timed public urination. While Nick and Sydney’s philosophies didn’t match, the conversation is a hilarious and honest look at how mismatched attitudes toward boundaries—and personal hygiene—can send a blossoming romance straight to voicemail.

Brooke & Jeffrey’s Second Date Updates: For mortifying stories and real dating lessons, tune in wherever you get your podcasts.