Second Date Update: "Escalator Escape"

Podcast: Brooke and Jeffrey: Second Date Update
Date: November 19, 2025
Host(s): Brooke & Jeffrey
Guest: Jamie (listener seeking a second date), Matthew (date)

Episode Overview

In this hilarious and unexpectedly poignant installment, the team helps listener Jamie discover why her promising first date with Matthew ended in radio silence. What begins as a story about overcoming an unusual phobia quickly escalates (pun intended) into confessions about exes, age-gap relationships, and some unintentional disses. By the end, the real reason behind the ghosting is revealed—and it’s not what anyone expected.

Key Discussion Points & Insights

1. Jamie’s Motivation for Dating Apps

• Jamie reveals she's on dating apps to regain confidence after recent breakups:
  • “I've just been trying to get myself back out there... I'm just trying to get my confidence back up. I don't really assume I'm going to fall in love immediately.” (05:05)
• Brooke is charmed by Jamie’s honest and lighthearted approach.

2. The Escalator Incident

• Jamie nearly cancels the date due to a severe phobia of escalators.
  • “The bar you picked is on the second floor, and you have to take an escalator there, and I have this phobia of escalators, basically.” (06:09)
• Reluctant to admit her fear to Matthew, Jamie asks him to hold her hand and closes her eyes while riding up:
  • “I just had him hold my hand while I sat on the elevator step and kept my eyes closed, and we rode up.” (07:19)
• Hosts empathize, share their own escalator fears, and joke about escalator horror stories.

3. Escalation of the Date (and Chemistry)

• Jamie and Matthew hit it off after the awkward start, bonding over a mutual, quirky love for JetBlue Airlines:
  • “It’s our favorite and they have the best in-flight entertainment.” (08:23)
• The night ends with Matthew asking Jamie out again—and her readily agreeing:
  • “At the end of the night, he even asked me if I wanted to meet up again. And I was like, yes, definitely.” (08:48)
• But after that, she hears nothing for a week.

4. The Confrontation Call: Why Did He Ghost?

• Jamie hasn’t reached out, hoping not to seem “obsessive or weird.”
• The team dials Matthew for the Second Date Update.
  • Brooke (11:52): “You're on a show right now, a radio show called Brooke and Jeffrey in the Morning.”
• Matthew is caught off guard but willing to talk.
• When asked why he ghosted, Matthew points to Jamie’s parting comment as the dealbreaker:
  • “She paused...and she goes, ‘Sure, why not? My bar is pretty low anyways.’” (13:43)
• Matters get stranger: Jamie also quipped that she just got out of a relationship with an 80-year-old man:
  • “She goes, ‘Don't take it personal. I just got out of a relationship with an 80-year-old guy.’” (14:12)
• Matthew was thrown. He didn’t know how to interpret her cracks—or her history.

5. The Truth Comes Out

• Jamie, on the line, joins the call:
  • “Okay, so you're putting me down just because I dated an older man.” (15:49)
• Matthew retorts:
  • “No, I'm putting you down because you dated an ancient man who kicked you to the curb.” (15:54)
• Jokes fly, but the conversation gets a little real about dating motivations, money, and self-worth:
  • “Honestly Jamie, the optics are… you’re just doing it for money. That’s the only reason anyone would date an 80-year-old at your age.” – Jeffrey (16:41)
• Jamie insists it was neither about money nor lack of attraction:
  • “He was in great shape. Probably better than you, actually. And he was very active...” (16:23)
• Tension escalates before the hosts steer the conversation back.

6. Resolution (Or Lack Thereof)

• Jamie apologizes for her insensitive joke, explaining she wasn't feeling good about herself:
  • “I just gotten out of something; I wasn't feeling good about myself, so I made a bad joke.” (18:13)
• After the dust settles, neither Jamie nor Matthew wants another date:
  • “Are you asking if I want to go out with him again? You know, I don't.” – Jamie (18:54)
  • “Yeah, I'm good as well. She can have that 80 year old man hold her hand up the escalator.” – Matthew (19:08)

Notable Quotes & Memorable Moments

• On Escalator Fears
  • “If you can’t see it, it can’t hurt you.” – Brooke (07:30)
• On Age-Gap Relationships
  • “You’re rebounding from an 80-year-old? That must feel good.” – Brooke (14:21)
  • “She basically says the 80-year-old broke up with her so he could find someone who lives closer to him.” – Matthew (14:35)
• On Dating Motivation Stereotypes
  • “You could at least go with personality over body. That’s more believable.” – Jeffrey (16:53)
• On Second Date Update Realities
  • “Jamie, you're the one. You reached out to our show. That's super low in itself. You're meant to meet down at the bottom of the dating pool.” – Jeffrey (18:41)

Timestamps for Important Segments

• Escalator Phobia Story: 06:01 – 07:41
• Bonding Over JetBlue: 08:16 – 08:35
• Matthew’s Explanation for Ghosting: 13:30 – 14:44
• Jamie Joins the Call—80-Year-Old Ex Revealed: 15:45 – 16:51
• Final Decision—No Second Date: 18:54 – 19:13

Episode Tone & Takeaways

The episode is a classic mix of humor and honest awkwardness. The hosts are playful but push for answers, while Jamie and Matthew’s dynamic oscillates between self-deprecating jokes and raw vulnerability. The show highlights how first-date nerves and jokes can unexpectedly sabotage budding chemistry, and how sometimes the issues aren’t about escalators at all.

Final Note:
If you’re struggling to reconnect after a great first date, make sure your jokes land—and maybe keep the 80-year-old exes out of your punchlines. As for Jamie and Matthew, they’ll be taking separate escalators from now on.