Brooke and Jeffrey: Second Date Update — "Awkward Tuesday: Nanny Zoned"

Date: November 11, 2025
Host: iHeartPodcasts
Episode Theme: When your childhood nanny can’t stop seeing you as a kid, even as an adult.

Episode Overview

This episode of Brooke and Jeffrey’s “Awkward Tuesday Phone Call” features Mark, a young man who has reconnected with his childhood babysitter, Kendra. After a surprisingly flirtatious catch-up dinner, Mark feels “nanny zoned”—Kendra sees him more as the little boy she used to babysit than a potential romantic partner. The hosts try to help Mark navigate this bizarre, comical situation to confess his adult feelings and see if a romantic spark is possible.

Key Discussion Points and Insights

1. Introducing Mark’s Dilemma

• [04:09-05:53] Jeffrey and Alexis kick off by teasing the concept of being “nanny zoned,” where someone can’t shake their view of you as a child.
• Listener Mark explains how he “randomly bumped into [his] old childhood babysitter” Kendra at a coffee shop, leading to a hilariously awkward reintroduction:

  “I just yelled, ‘Kendra?’ … She was just like, ‘Who are you?’” — Mark ([06:08])

• After reminding her who he was (in a baby voice, at that!), Kendra remembers him and is excited. Mark admits he finds her "super cute now."
• They exchange contact info and later catch up over dinner.

2. Dinner Turned Weirdly Parental

• [07:51-09:20] Mark describes the dinner feeling flirty and comfortable due to their history.

  “She was twirling her hair, she was laughing. It was amazing.” — Mark ([09:05])

• But things shift when Kendra leans over and says, “Marky, you need to finish your vegetables.” Mark laughs it off, but Kendra insists.

  “I ate my vegetables while she watched. It was embarrassing.” — Mark ([09:45])

• At the end of the night, Kendra tells him to text her, adding, “It’s important to keep promises”—once again, very babysitter-like.

3. Seeking Host Advice

• [10:22-11:16] Mark expresses a desire for Kendra to “see me as someone that can be with you,” instead of a kid.

  “I just need advice... Just to say that I’m grown and... can be with you.” — Mark ([10:28])

• The hosts suggest Mark casually reference his adult life, travels, and past relationships, so Kendra sees him as more than “Marky.”

  “You have to switch her mindset... I think you should bring up exes.” — Brooke ([12:15])

4. The Awkward Phone Call: Mark and Kendra Reconnect

• [13:46-20:13] Mark calls Kendra, admitting his childhood crush.

  “When I was 9, I kind of had a crush on you.” — Mark ([14:33])
  “Tell me something I don’t know... I kind of had a feeling. ...when my boyfriend stopped by that one time you called 911…” — Kendra ([14:41])

• As conversation continues, Kendra keeps referring to Mark as “Marky” and making parental comments:

  “I felt like I was keeping you up past your bedtime.” — Kendra ([15:23]) “Everybody needs their sleep, even big boys like you.” — Kendra ([15:39])

• Mark finally addresses the dynamic:

  "I feel like I’m being nanny zoned... This is stuff you would have said to me as a kid. I don’t want the potential of this to have the same nanny-kid power structure.” — Mark ([16:19])

• Kendra playfully offers:

  "How about you come over to my place this Friday, I'll make you dinner and I won't make you eat vegetables. ...you can stay over ...and I'll read you a bedtime story and tuck you in." — Kendra ([17:03])

5. Hosts Intervene and Meta-Discussion

• [17:32-20:25] The hosts jump in, explaining the segment and Mark’s true motive.

  “Do you feel like there’s a connection there? Maybe, Kendra? Like a grown up, mature, romantic connection?” — Jeffrey ([18:19])

• Kendra admits some attraction but struggles to see Mark as an adult:

  “It’s really hard to shake the image I have of you as a little boy. ...he’s just Marky and I can’t.” — Kendra ([18:26], [19:00])

• Alexis and Jeffrey encourage Mark to demonstrate he’s grown up:

  “But listen to his voice... that’s a man voice. ...He’s got facial hair.” — Alexis ([18:41]) “I mean, I do have facial hair. I mean, come on.” — Mark ([18:52])

6. Resolution: “Nanny Zoned” For Good

• [20:13-20:54] Consensus emerges: the dynamic is just too ingrained.

  “Maybe you guys can be friends or you can stay nanny zoned…” — Alexis ([20:19]) “Yeah, I think that’s fine for me.” — Kendra, confirming friendship is best ([20:36])

• Lighthearted quips about Mark still yearning for “bedtime stories” end the segment on a comedic note.

Notable Quotes & Memorable Moments

• Mark’s baby-voice introduction

  "Can you put on my footy pajamas?" — Mark ([06:36])

• Mark’s bold confession

  "When I was 9, I kind of had a crush on you." — Mark ([14:33])

• Kendra, playfully scolding

  "Everybody needs their sleep, even like big boys like you." — Kendra ([15:39])

• Mark, calling out the ‘nanny zone’

  “I feel like I’m being nanny zoned. ...This is stuff you would have said to me as a kid.” — Mark ([16:19])

• Kendra, unintentionally reinforcing the dynamic

  “You can stay over and I'll read you a bedtime story and tuck you in.” — Kendra ([17:19])

• Hosts, slyly underscoring the weird:

  “Maybe the tickle monster can come out again and be like… the grown up tickle monster.” — Jeffrey ([19:57])

• Mark, embracing it:

  “I like when she reads me bedtime stories.” — Mark ([19:52])

Timestamps for Important Segments

• [03:07] — Veterans Day greeting, setting the episode’s tone
• [05:53] — Mark joins to explain his awkward dilemma
• [06:36] — Mark’s baby-voice moment
• [07:51] — Description of the reuniting dinner and its tone
• [09:28] — The moment Mark is “nanny zoned” at dinner
• [12:15] — Brooke’s key advice: “Switch her mindset”
• [13:46-20:13] — The phone call between Mark and Kendra (core of episode)
• [16:19] — Mark directly addresses being “nanny zoned”
• [17:03] — Kendra’s dinner (and bedtime) proposal
• [18:26] — Kendra admits attraction but is “stuck” in the past dynamic
• [20:25] — Hosts guide toward the friend zone
• [20:54] — Kendra and Mark agree to just be friends

Tone and Style

• Playful, teasing, and energetic: The hosts frequently rib Mark and banter about the scenario while offering empathetic, if cheeky, advice.
• Candid and self-aware: The show never shies from how odd and comedic the entire situation is, with frequent meta-commentary.
• Heartfelt but realistic: While everyone roots for Mark, they accept that some dynamics might be too deep-rooted to change.

Conclusion

“Nanny Zoned” delivers outsized laughs and a healthy dose of empathy, proving just how hard it can be to escape outgrown roles from childhood. Despite flirtation and chemistry, the power dynamic is too entrenched for romance (for now), and Mark and Kendra settle for friendship—with a wink toward bedtime stories and “big boy” jokes. The hosts deftly balance humor with genuine support, making this an episode both entertaining and surprisingly sweet for listeners.

Memorable Sign-off:

“What’s your favorite bedtime story, Mark?”
“Oh, I got Thumbelina.” ([20:54])