The Bert Show – Vault: Babysitting Horror Stories
Date: November 7, 2025
Host: Pionaire Podcasting
Episode Theme: Real-life babysitting disasters and the hilarious, awkward, and sometimes terrifying experiences shared by the hosts and listeners.
Episode Overview
This episode plunges into the wild world of babysitting gone wrong as The Bert Show cast and their callers recount their absolute worst (and funniest) babysitting stories. From kids locking sitters out, to animal and child mishaps, to truly uncomfortable encounters with parents, the episode strikes a funny, nostalgic, sometimes cringeworthy tone that both commiserates and entertains.
Key Discussion Points & Insights
Opening: Setting the Babysitting Scene
- Jeff & Elizabeth reminisce about their own babysitting backgrounds.
- The conversation kicks off with a retelling of the prior day's “lockout” babysitting story, segueing into listener submissions of their own adventures.
- Jeff: “I have never babysat in my life. I don’t know how I was okay with it…” (02:21)
Section 1: Lockout Fiascos
- Jennifer (Intern): Shares a story of being locked out by a frustrated 10-year-old while babysitting.
- Jennifer: “The kid and I were playing in the yard and he got pissed and ran inside the house and locked me outside.” (02:00)
- Caller Erin: Babysitting overnight, gets locked out with a child, must break in, accidentally locks the family cats in her car who use it as a litter box all night.
- Erin: “The cats were in my car for about 14 hours.” (05:10)
Section 2: Heart-Stopping Kid Escapades
- Caller (Elizabeth or Michelle): Babysitting a 6-year-old who locks her out, then crawls onto the roof from the second floor. She must rescue him.
- Caller: “Had to climb out onto the roof to get him back in.” (05:52)
- Jeff: “$4 an hour and you’re crawling on the roof to rescue a squirmy six-year-old?” (06:03)
Section 3: Armed and Not-So-Dangerous?
- Caller (Elizabeth or Michelle): Recounts a babysitting gig where the single mom shows her a loaded handgun, instructing her to “shoot first, ask questions later” if the ex-husband comes by.
- Caller: “She showed me where the handgun was. It was loaded…and let me know if her ex-husband showed up to shoot first and ask questions later.” (06:23)
- Elizabeth: “Your four bucks an hour is not going to be worth it, lady.” (06:42)
Section 4: Eerie Baby Monitor Incident
- Host (The Bert Show): While babysitting, hears a creepy voice over the monitor coaxing a child to sleep—thinks someone is in the house, but it’s just the neighbor’s baby monitor bleeding over.
- Host: “It is the neighbors next door...so I could hear their baby monitor trying to put him asleep but I flipped out.” (08:14)
- Jeff: “The call came from inside the house.” (07:38)
Section 5: The “Poop Picasso” & Literal Messes
- Caller Jessica: Babysits two boys. Returns to find the 6-year-old has smeared feces on the walls.
- Jessica: “I come back in the living room and the oldest...smeared it all over the wall.” (08:52)
- Elizabeth: “No, no. If your child is wiping poop on the walls, then you stay home during that phase.” (09:02)
Section 6: Babysitter Gets Accused
- Caller Michelle: After a babysitting gig, is accused of theft by the boy’s mother, must go to court, is found innocent but traumatized.
- Michelle: “I was 15 years old, I get read my rights. They were going to arrest me. I had to go to court…” (09:58)
- Jeff: “Did anybody…have to go to court? Testify?” (10:15)
Section 7: Violence with Household Implements
- Caller Laura: Chased by a child wielding a golf club. Has to lock herself in the house and call her dad for rescue.
- Laura: “This kid was just a kid from hell and went out to the garage, got one of his dad's golf clubs and started to try and chase me around the house.” (13:02)
- Caller Melissa: Babysits for Bon Jovi tickets; gets chased with a knife by a child upset that chore time interrupted his movie watching.
- Melissa: “He proceeds to throw a temper tantrum and picks up a knife and chases me and his little sister…” (14:00)
- Elizabeth: “Dude, what is that little kid doing now?” (14:31)
Section 8: The Dangers of Parent Pickup
- Elizabeth: Shares how the worst part of babysitting was rarely the kids, but rather dealing with intoxicated or inappropriate parents.
- Elizabeth: “One time I had to call my mom to come and get me because the dad who wanted to drive me home was so wasted...” (11:29)
- Describes a dad making her deeply uncomfortable with “shoulder touching... rubbing of the neck in the car...slurry flirting thing while he's trying to figure out how much money he owes you.” (12:14, 12:34)
Section 9: Undergarment-Tree Incidents
- Caller Anna: Babysitting on a farm; loses track of the child, finds her after 35 minutes literally hanging from a tree by her underwear, resulting in a massive wedgie and burns.
- Anna: “She’s hanging from her underwear off of a tree branch...her parents are like, what's going on?” (14:59, 15:56)
- Jeff: “You do not want the parents to come home when you've got the kid on your lap with no underwear and burn marks.” (16:01)
Notable Quotes & Memorable Moments
- “The cats were in my car for about 14 hours.” — Erin, on the feline lock-in debacle. (05:10)
- “I went once and I called her back and said, sorry, I don't think it's going to work.” — Caller after being told to shoot the ex-husband on sight. (06:38)
- “It is the neighbors next door on the street...so I could hear their baby monitor trying to put him asleep, but I flipped out.” — Host, after the baby monitor scare. (08:14)
- “No, no. If your child is wiping poop on the walls, then you stay home during that phase.” — Elizabeth, on babysitter boundaries. (09:02)
- “$4 an hour and you're crawling on the roof to rescue a squirmy six-year-old?” — Jeff on the perils versus pay of babysitting. (06:03)
- “Sometimes they wouldn’t, like, pay you till the end of it, too, so you don’t want to be like, you know...” — Elizabeth, on tolerating creeper dads for the paycheck. (12:34)
- “She’s hanging from her underwear off of a tree branch.” — Anna, on farm babysitting fails. (14:59)
Key Timestamps
- 01:47 — 02:21: Intern Jennifer’s original lockout story
- 04:32 — 05:26: Overnight lockout & cats in the car – Erin’s call
- 05:36 — 06:11: Rescue mission from a roof after being locked out – Caller
- 06:17 — 06:44: The loaded handgun babysitting call
- 07:38 — 08:23: Baby monitor horror story
- 08:31 — 09:13: Jessica’s catastrophic “poop Picasso” babysitting gig
- 09:25 — 10:36: Michelle’s wrongful theft accusation and court saga
- 13:00 — 13:33: Laura’s golf club pursuit escape
- 14:00 — 14:49: Knife-wielding child terror
- 14:59 — 16:08: Anna’s epic tree wedgie rescue
Summary & Takeaways
The episode is a comedic, cautionary tale about the chaos that can ensue when kids, pets, and, sometimes, parents conspire against the good intentions of babysitters. The Bert Show crew and their callers share stories that are both horrifying and hilarious, often spotlighting the inadequate pay compared to the perils and unpredictability of the gig.
Despite the trauma and chaos, everyone manages to laugh—if a bit nervously—about their “Babysitting Horror Stories.”