Armchair Expert with Dax Shepard

Armchair Anonymous: Babysitting II

October 31, 2025

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  • The 'Armchair Anonymous: Babysitting II' episode features listener stories ranging from financial irresponsibility by a babysitter to terrifying home invasions and even a connection to a past murder case. 
  • One caller's babysitter took her children on an unapproved $340 shopping spree, leading to immediate termination of her employment. 
  • Another caller recounted a harrowing experience where she was physically assaulted by an intruder while babysitting, who she later identified in court, though he was ultimately found not guilty. 
  • The guest, identified as Macy, shared a traumatic experience involving a home invasion and assault while babysitting, which prompted her long-distance partner to immediately drive to her location out of protective concern. 
  • The story shared by Macy was immediately suggested by her mother to be submitted as an anonymous story for the podcast, leading to its inclusion in this episode of *Armchair Anonymous: Babysitting II* on *Armchair Expert with Dax Shepard*. 
  • The conversation concludes with promotional information for following *Armchair Expert with Dax Shepard* on various platforms and joining Wondery+ for early, ad-free access. 

Segments

Introduction and Host Setup
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(00:00:14)
  • Key Takeaway: Karen Beekman is filling in for Monica on ‘Armchair Anonymous: Babysitting II’ to hear wild babysitting stories.
  • Summary: The episode opens by introducing Karen Beekman as the substitute host for Monica. The theme for this segment of ‘Armchair Anonymous: Babysitting II’ is explicitly stated to be wild, non-cutesy babysitting stories. The segment also includes sponsor reads for Nordic Naturals and Cachava.
First Caller: Mall Spending Spree
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(00:03:39)
  • Key Takeaway: A babysitter, who was also a vet tech, took the children on an unapproved mall trip resulting in $340 in expenses.
  • Summary: Caller Stephanie, a nurse, recounted a new babysitter taking her children to the mall without permission, leading to significant spending on toys and candy. The babysitter later defended the spending by suggesting the children should have been given a cash limit beforehand. The caller’s family decided not to rehire the sitter due to the incident.
Second Caller: Tutor’s Mental Health Crisis
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(00:14:52)
  • Key Takeaway: A former math tutor, who was also babysitting the caller’s friend’s daughter, was arrested for murdering a 16-year-old girl.
  • Summary: Caller Kate shared a story from her youth involving a math tutor who was initially described as having mental health issues, leading to him stopping tutoring sessions. Later, it was revealed the man was arrested for murdering a 16-year-old girl he met online, though he was later found not guilty at trial. The caller saw the man in public the day before his arrest, and the incident caused her friend’s family to move away.
Third Caller: Home Invasion During Babysitting
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(00:35:14)
  • Key Takeaway: A 19-year-old babysitter fought off an intruder who broke into the house while four young children were asleep upstairs.
  • Summary: Caller Macy detailed an incident where an intruder entered the house while she was babysitting four children in Toronto, dragging her through the house and throwing her into a Christmas tree. She managed to kick the intruder in the testicles, allowing her to call 911 and take a photo of him before he fled, which later aided in his arrest for sexual assault.
Partner’s Protective Reaction
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(00:48:42)
  • Key Takeaway: The guest’s long-distance partner reacted with immediate, intense concern and planned to drive to her house after learning about the assault.
  • Summary: The partner, described as a protector, was informed via text message about the home invasion and assault, though the guest confirmed she was safe. He immediately began driving to her location the following morning due to his protective nature. The guest expressed appreciation for this protective instinct.
Story Submission Origin
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(00:49:16)
  • Key Takeaway: The idea to submit the traumatic babysitting story for the podcast originated from the guest’s mother the day after the incident occurred.
  • Summary: Macy’s mother suggested the event would make a good anonymous story immediately following the incident. This suggestion was quickly adopted, leading to the story being shared on Armchair Anonymous: Babysitting II. The guest noted this as a thin silver lining to the experience.
Closing Remarks and Promotion
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(00:49:39)
  • Key Takeaway: The hosts noted a pattern where half of their babysitting stories involve intruders entering the house, followed by standard podcast sign-off and subscription prompts.
  • Summary: One host observed that a significant portion of their collected babysitting narratives involve unauthorized entry into the home. The segment concluded with expressions of mutual appreciation between the guest and the hosts. Listeners were then directed to follow Armchair Expert with Dax Shepard on Wondery or other platforms and join Wondery+ for early access.