Podcast Summary: Armchair Expert – Armchair Anonymous: Babysitting II

Date: October 31, 2025
Host: Dax Shepard (A) with guest host Karen “Erin” Beekman (B)

Episode Overview

This episode of Armchair Anonymous explores the wild, unexpected, and sometimes harrowing world of babysitting. Dax and guest co-host Karen/Erin Beekman invite listeners to share their most outrageous babysitting stories, featuring everything from financial chaos and family drama to true crime encounters and moments of bravery. While the hosts maintain their signature mix of humor and empathy, the stories traverse the full spectrum of the messy, unpredictable human experience that defines this podcast.

Key Segments & Stories

[03:37] Stephanie – "The $340 Cat Sitter"

Story Highlights

• Stephanie is a nurse and a mother of two “spirited” kids.
• The family adopts a stray cat; soon after, a new, barely-known family babysitter starts.
• First day: chaos. The cat’s missing, one kid’s crying. The sitter handles it all, claims “I got this.”
  • Notable quote:
    “I haven’t ever had a sitter say that to me. Like, you go, I got this.” – Stephanie [05:00]
• Stephanie’s daughter FaceTimes her from the mall—unexpected since they’re supposed to be home.
• At the end of the day, the sitter texts:
  “We ended up spending about $340. I can give you the receipts.” – Stephanie quoting sitter [08:10]
• $250 spent at PetSmart, “very large bags of candy,” and assorted cat paraphernalia.
• Drama ensues with the parents trying to get answers and returns; awkward group texts follow.
• The sitter blames the family for not giving the kids a spending limit before taking them to the mall.
• The adopted cat turns out to have an owner, and the family has to give it back (but ends up adopting a kitten).
  • Notable quote:
    “From the beginning, your kids should have been given cash or a limit of money to spend.” – Sitter (read by Stephanie) [11:42]

Insights & Takeaways

• Parent awareness and clear communication are critical for sitters.
• The ripple effect of small chaos (adopting a stray, hiring a “sort-of” family member) can snowball.

Memorable Moment

• Dax’s suggestion:
  “If you get invited to the wedding, I beg you to wrap up all those cat toys and make that the present.” [13:02]

[14:49] Kate – "The Babysitter, The Tutor, and a Chilling True Crime"

Story Highlights

• Kate, an “army brat,” starts babysitting for a British family after moving to the West Coast.
• Becomes the regular sitter for multiple families, including a neighbor whose dad starts tutoring her.
• The dad suddenly stops tutoring her amid vague allegations of “mental health issues.”
• Much later, it emerges he was fired from a school over “inappropriate” behavior, wife leaves him, the community whispers.
• Kate (age 17) accidentally runs into the man at Target; he panics and flees.
• The next day, Kate’s mom receives a call: the man has been arrested for murdering a 16-year-old girl he met online.
  • Notable quote:
    “He’s the one who did it. He had kept the knife and the bloody clothing...” – Kate relaying phone call [25:33]
• The killer gets just 20 years, is now out.
• Kate and her friends process having been close to someone capable of terrible acts.
• Dax and Erin discuss the impossibility of “knowing” who is dangerous:
  • “I think we all would love to believe we could somehow smell that out and we can’t.” – Dax [27:18]

Insights & Reflections

• Even “nice guys” can have hidden dangers; hindsight and community rumors can't keep kids safe.
• Story prompts reflection on the shaky line between sanity and insanity.

Memorable Quotes

• “We had a couple creepies, but never would have guessed that the man I used to babysit for killed a girl my age.” – Kate [26:36]
• “You don’t bump into a lot of people whose babysitters murdered people.” – Dax [28:10]

[30:41] Jeff – "The Sleeping Babysitter and the Missing Child"

Story Highlights

• Jeff, now on vacation in Greece, tells a story from his Canadian 1980s teenage years.
• Volunteered by his mom to babysit a single dad’s 3-year-old son.
• Duties: Arrive, eat snacks, watch TV, “kid will already be in bed.”
• Jeff never sees the kid, dozes off on the couch.
• Arrives home to find his own mom frantic: the dad called, can’t find his son.
  • Notable quote:
    “I never saw the kid. I didn’t go upstairs. I had no idea where the son was.” – Jeff [34:50]
• Turns out, the estranged ex-wife (barred from visits) snuck in, abducted her child while Jeff slept.
• Dad retrieves son after confronting the ex-wife, but ends up facing assault charges (for breaking in and fighting the boyfriend).

• Jeff is called as a (comically useless) court witness.

  “Did you go upstairs?”  
  “No, I didn’t go upstairs.” – Jeff in court [37:36]
  

• Dax jokes about Jeff’s (lack of) effectiveness: “You’re useless. You might as well not have anyone there.” [36:20]

Takeaways

• Sometimes the system is more concerned with legal technicalities than intent or outcome.
• The “babysitter asleep on the job” trope becomes very real…and memorable.

[39:07] Macy – "Home Invasion Heroism"

Story Highlights

• Macy, just moved to San Jose from Toronto, recalls an incident while babysitting four young kids in Toronto.
• As all the kids are (finally) asleep, Macy settles in for “snack time.”
• She hears strange noises; a man enters the house through the back door, saying, “Get down, I’m hiding from somebody.” [43:17]
• The man grabs Macy’s wrist and drags her around the house, turning off lights, searching for hiding spots.
• Macy maintains composure, carefully suppresses panic to avoid alerting the kids.
  • Notable quote:
    “He could not go upstairs to those children.” – Macy [44:55]
• In a violent struggle by the Christmas tree, Macy gets pinned, but remembers self-defense advice, kicks the man three times “where I knew it would hurt him the most.”
  “It worked. He collapsed immediately, in so much pain, finally releasing his grip.” [46:48]
• Macy takes a photo of him as evidence, calls 911 (unsuccessfully at first), and the intruder flees.
• Police later ask her to identify him; he’s caught, but ultimately found not guilty in court.
• Macy describes the aftermath: night terrors, regret for not triple-checking locks, defiant optimism.
  • Notable reflection:
    “Obviously it was traumatic, but what are the odds that’s going to happen to me again? ... I do triple check the locks.” [51:58]

Insights & Reflections

• Even in "safe" neighborhoods, danger can arrive unexpectedly.
• Macy’s clarity and quick-thinking under duress saved herself and the children—a testament to her strength.
• Systemic failures: 911 fails to answer; criminal remains at large.

Memorable Moments

• Dax and Erin’s incredulity over 911’s voicemail:
  “What, they have voicemail at 911?” – Dax [44:29]
• Macy’s post-trauma perspective:
  “If I can overcome that, I think I’ll be okay.” [52:25]

Notable Quotes

• On Parenting & Chaos:
  “It’s the ripple effect of small chaos...can snowball.” – Dax, summarizing Stephanie’s saga [08:58]
• On Evil & Sanity:
  “There’s a fine line between sane and insane. And it takes something very simple to push that.” – Kate [27:22]
• On System Failures:
  “Toronto 911. Get it together.” – Dax [46:58]
• On Babysitting as a Right of Passage:
  “I think the thing I’d love most about being a babysitter is going into people’s houses and them having snacks.” – Dax [29:38]
• On Empathy from Trauma:
  “I have a lot of empathy and you never know what tomorrow brings, so you better have fun today.” – Kate [28:38]

Other Memorable Moments

• Dax confesses a deep love for nurses, likening them to Navy SEALS for their resilience with the “duty and blood and yawn” of their work. [04:13]
• Jeff’s mom being “frantic at the end of the driveway”—cinematic, humorous, and deeply human. [34:20]
• Macy’s resourcefulness in taking a photo of the intruder for evidence, even before police arrive. [47:01]
• Dax recounts his own strange babysitting memory, where his dad made him lie about his age to babysit someone his own age—a moment of embarrassment and adolescent awkwardness. [29:53]
• Humor and camaraderie run through the entire episode, even (or especially) among the most harrowing tales.

Timestamps of Key Segments

• Introduction and banter: [00:00 – 03:37]
• Stephanie’s “$340 Cat Sitter” Story: [03:37 – 14:47]
• Kate’s “The Tutor True Crime” Story: [14:49 – 29:10]
• Jeff’s “Sleeping Babysitter” Story: [30:41 – 38:59]
• Macy’s “Home Invasion Heroism” Story: [39:07 – 53:28]
• Host reflections and sign-off: [53:28 – end]

Episode Tone & Style

Throughout, Dax and Erin maintain a warm, irreverent, and supportive tone—balancing humor with empathy, even as stories take unexpectedly dark or emotional turns. The guests’ honesty, vulnerability, and storytelling skill make this an engaging, relatable listen for anyone reflecting on the unpredictability of caretaking, childhood, and trust.

Final Thoughts

• Babysitting, often dismissed as mundane, can become a crucible of character, drama, and growth.
• Trust and communication are essential—and sometimes, the best one can do is “just keep on shining” even when the world throws curveballs.
• As Dax sums up:
  “We weren’t expecting murder in babysitting.” [29:20]
• The episode is a powerful reminder: Everyone has wild stories—and it’s the sharing of them that both heals us and brings us together.