Armchair Anonymous: Babysitting II

31 Oct 2025 · 48 min

Ask about this episode

Ask anything about it. ChatGPT or Claude reads this page and answers with the times it was said.

Connect VO and ask about every podcast you hear, including the moments you saved. Add to ChatGPT · Add to Claude

In short

Armchair Expert - Armchair Anonymous: Babysitting II

Podcast Overview Host: Dax Shepard Guest: Monica Padman (filling in for Monica) Episode Theme: Crazy babysitting experiences shared by listeners (Armcherries).

Episode Summary This episode features a series of wild and sometimes alarming babysitting stories shared by listeners. The stories highlight the unpredictability and challenges of babysitting, with humor, drama, and an exploration of the human experience.

Key Highlights

Introduction

  • Dax and Monica introduce the theme of the episode: crazy babysitting stories, indicating that the stories will be more wild than typical anecdotes of boredom and pizza.

Story 1

Stephanie's Experience

  • Background: Stephanie, a nurse, shares a babysitting experience involving a new sitter for her children.
  • The Babysitter: Hired through family connections; seemed great with kids.
  • Unexpected Mall Trip: The babysitter took the kids to the mall and spent an excessive amount ($340) on items, including pet supplies and toys, without prior approval.
  • Communication Breakdown: The parents were shocked upon learning of the spending; the babysitter's defensive response led to a tense situation.
  • Conclusion: The babysitter was not invited back due to financial concerns, and humorously, they had to return a cat they had just adopted.

Story 2

Kate's Experience

  • Setting: Kate recounts an unsettling babysitting story involving a family with a father who had mental health issues.
  • Innocent Beginnings: She started babysitting for a neighbor's family and ended up also babysitting for a father who was pursuing a teaching degree.
  • Dark Twist: The father was later arrested for the murder of a teenager, which unfolded in a shocking revelation that left Kate reflecting on her past experiences and the innocence lost.

Story 3

Macy's Terrifying Encounter

  • Incident: At 19, while babysitting a family of four, Macy faced a terrifying confrontation when an intruder broke into the home.
  • Confrontation: The intruder, believing he was hiding from someone, physically restrained her.
  • Bravery and Self-Defense: Despite the fear, Macy managed to fight back using self-defense techniques she had learned.
  • Aftermath: The police were eventually called, and although they apprehended the intruder later, he was found not guilty in court due to insufficient evidence, leaving Macy with a sense of unresolved trauma.

Key Themes and Insights

  • Human Vulnerability: Each story illustrates the inherent risks of trusting others with the care of children and the unpredictability of human behavior.
  • Adapting to Chaos: The narrators demonstrated resilience and quick thinking in challenging situations, showcasing the importance of remaining calm in crises.
  • Trust and Betrayal: The theme of trust is prevalent, as all stories revolve around the complications that arise when that trust is violated.
  • Humor in Darkness: Despite the serious nature of some stories, humor often emerges as a coping mechanism for the storytellers, making light of absurd situations.

Closing Remarks

  • The episode concludes with an acknowledgment of the unpredictability of babysitting and the unique bond formed between sitters and the families they care for.
  • Dax and Monica reflect on the shared experiences and the stories' emotional impacts, thanking the listeners for their contributions.

Key Takeaways

  • Babysitting can lead to unexpected and sometimes perilous experiences.
  • Resilience and humor are vital in navigating the complexities of human relationships and unexpected events.
  • The importance of careful vetting and clear communication when hiring babysitters is emphasized through the shared anecdotes.

---

Note: This markdown document captures the essence of the podcast episode, summarizing the discussions, highlighting key stories, and providing insights into the themes addressed.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Hear the part that matters, and keep it.Open this episode in VO. Double tap your headphones to save a moment as you listen.
Get VO free

Transcript

Automatic transcript. May contain errors.

0:00Wondery Plus subscribers can listen to Armchair Expert early and ad-free right now. Join Wondery Plus in the Wondery app or on Apple Podcasts, or you can listen for free wherever you get your podcasts. Welcome, welcome, welcome to Armchair Anonymous. I'm Dan Shepard, and I'm joined by Sharon Beekman. Thank you, Sharon. Hello, it's me, Karen. Karen Beekman. Filling in for Monica, away on family business. Today we have crazy babysitting stories. Some real good ones. Really good ones. Don't think that this is going to be cutesy time eating pizza and being bored. These get wild. Crazy. Crazy. Please enjoy Crazy Babysitting Stories.

1:03Stephanie? Stephanie, yes. Are you in the medical industry? I am. Okay, so much to go through. Love your earrings. I see some instruments behind you. What capacity do you work at the doctor? I'm a nurse and I teach nursing at a school of nursing. So this is actually a simulated lab. I thought you would appreciate this simulation in progress. It's always in progress though, isn't it? Yes. Am I being clear enough that I love nurses? That was honestly part of the reason why I was like, I think I should do this in somewhere, but it makes it obvious that I'm a nurse. Aaron, do you love nurses? Of course.

1:38Yeah. How do they do it? I have no idea. We're the best. We can be a little dark sometimes, though. But always really funny because of that. Call it what it is. Like the amount of duty and blood and yawn that you guys have to deal with. You seem to do it without being ruffled at all. There's like Navy SEALs and you guys are like tied. Okay, so you have a babysitting story. First of all, are you excited? Best for an Aaron Weekly sitting in today? I'm so excited. I was not expecting that. Sorry, I'm filling in today. I love it. So yeah, I have two kiddos, a daughter who's 11 and a son who's nine.

2:11And we'll call them spirited. Some may say feral, but you know, they're a party. That's my kind of kids. They need a good sitter. Sometimes it's not always easy to find a solid one. To give you a little backstory, because this will all kind of come around. We have a small cabin up at the base of Mount Adams in a small little town that we go to on the weekends in Trout Lake, Washington. So it's about 30 minutes from Hood River, actually. Oh. We spend a lot of weekends up there in the summer, especially. It's on fire about half the time, yeah? A little bit, yeah. Increasingly so. And so we were there over the summer, kind of right before the kids were going back to school.

2:51And this cat started hanging around our house, which isn't unusual in Trout Lake because I grew up there. People have a lot of cats and they hang around and they're always usually indoor outdoor cats. But this cat was really clinging on to us and we were kind of falling in love with it. It was coming around pretty much every weekend we were there. And then my mom, who lives next door, was feeding it when we weren't there. So eventually we were like, let's just take the cat. My mom's like, just take it. No one owns it. So we take the cat and we were pretty happy with the cat. We bring the cat back to Washougal where we live.

3:26The week that we bring this cat back coincides with the week that we've started this new babysitter. We got her through my husband's nephew. So his adult nephew had a fiance who was like, hey, I'm not busy for these couple of weeks. I'd love to help out. We just needed her for two weeks. So we kind of knew her. We'd met her at a few family functions. We just didn't know her really well, but she seemed super great with kids. Kids seemed to really love her. It's like, great. She comes and it's a bit of chaotic scene when she arrives, which isn't unusual, you know, with my children. One kid's crying, the cat's missing in the house.

4:01And I'm like, I gotta go. I felt a little bad, but she was so amazing. Like she walked in and she was like, I love animals. I'm a vet tech. She was like, I got this. You go to work. And I haven't ever had a sitter say that to me, like, you go, I got this. So I was like, wow. When I left, I said, hey, if you guys go out today, can you pick up some kitty litter? Because we didn't have any kitty litter for the cat. So at noon, my daughter FaceTimes me. I step out of my class because she doesn't normally FaceTime me in the middle of the day. She's so excited because she's at the ball. And I was like, oh, okay.

4:39It's a little weird. I didn't know you're going to the mall, but all right. We don't live close to the mall. We're like probably 30 minutes away from the mall. So I was like, it's a little odd. I can see my son in the background on one of those bungee things, you know, in the food court area. My son's like in the background and she's like, we're having so much fun. She just wanted to tell me that. So I hang up. I'm like, that was kind of strange that she didn't tell me she was going to take the kids to the mall, but I can overlook it. I needed her. She seemed really great. She's like 22. Beggars can't be choosers.

5:08Right. This was very blasphemy. It's like, it's fine. So then fast forward to me driving home and my husband was getting home before me. So I knew he was going to pay her for the day and send her off. And then I was going to be home later. So I text her on my way and I'm like, hey, thanks so much for today. Let me know what I owe you for the cat litter. This is what time I need you tomorrow. She responds back and she's like, we had such an awesome day. The kids were so much fun. We ended up spending about$340. I can give you the receipts. Oh my, what? How many times did your kid ride that fucking bouncy court?

5:42Three. And so I was driving and I was like, maybe she meant$40. I'm going to deal with this when I get home. So I get home. My husband had had a rough day. He owns a concrete finishing business. So he'd had a long day. He kind of did like a man cave thing, went into his room, turned on a football game, poured a beer. So I come home and the kids are out like playing with the cat. And I'm noticing like a lot of things in my house. A lot of cat toys that I didn't own. A very elaborate princess cat bed. A leash and a collar and a harness. Like taking this all in, I'm like, Ken's, why a harness and a leash?

6:17And she goes, I don't know. The babysitter said we needed it. I'm just like looking around and seeing toys. And then each kid has a very large bag of candy. It's like on those shopping markers, sweepstakes. It's like they got to fill up a cart, it sounds like. They sure did. I'm just sort of like, okay, I'm sure Kevin knows about this because he would have lost it. So I go into the bedroom. Did you notice any of the stuff out there? And he's like, what stuff? Man cave, beer, football. I noticed the tight end is injured. I love you, Kevin. We have a cat. Right. What fucking cat are you talking about?

6:55I said, do you talk to the sitter about their trip to the mall today? And he was like, no. I was like, did she tell you how much they spent? And he was like, no, I just paid her for the day. She said, you were paying her for the cat litter. And I said, have they spent$340 at the mall today? And I thought he was going to have a stroke. We're sitting in there trying to figure out like, what are we going to do? We've dealt with a lot of things with babysitters, but this was a first for us. And she's family kind of. So we're like, what do we do? He texts her and he's like, hey, Stephanie, let me know that you guys spent$340.

7:28That's about$300 more than we were planning on spending today. can you take some of this stuff back? Okay, great, great, great. And she was like, well, I wasn't there when they opened it. So I don't even know what can be taken back. She got pretty defensive. There was like 24 to 48 hours of some pretty strange texting that went on. And does the cousin hop on, on a side chat? Well, no, she included him in a group text to both of us. He won't answer his phone. Yeah. Good for him. My husband's like really good at resolving conflict. So he was like, I'm just going to call him and talk to him on the phone.

8:03They wouldn't answer. I interviewed the kids separately because I'm like, I need to know what happened today. And they both had the same story. And my son would throw my daughter under the bus any chance he got. So I do believe the story. They were headed out and my daughter's like, Hey, we need to get cat litter. So the sitter was like, why don't we just go to PetSmart? and they were like, okay. So they go to PetSmart and they spent$214 was the receipt that I got for PetSmart. And then my daughter wanted to go to Ulta. She said, can I go to Ulta and get a bath bomb? Cause she had some money on her card.

8:39So the sitter's like, why don't we just go to the mall? Took them to the mall and she just like went for it. And then the kicker for me was at the end, what she ended up saying to me in the text was I wrote it down because I saved all these text messages. She said, from the beginning, your kids should have been given cash or a limit of money to spend. And I said, if I would have known you were taking them to the mall, I would have done that. I didn't know we were going on a field trip. Needless to say, we did not ask her to come back because we were going to be broke. So if she came back again, the kids were like, we loved her.

9:16But she was great. Yeah. Yeah. But the real salt in the wound was at the very end. A couple of days later, my mom calls me and she's like, I have some bad news. The cat has a home. Oh, the owner's looking for the cat. Yeah. So we had to take Princess back. And did you give the owners all this bullshit that the babysitter bought? I didn't. No. but my husband felt really bad because we were all really upset because we'd really connected with this cat so we got a kitten out of the deal oh okay well that kind of worked out he's smart he's like i'm gonna give him this kitten i'm gonna go back to my cave yes have you spent any time trying to get into the psychology because my thought is like oh this woman's like a shopaholic she couldn't even resist on this day of babysitting and then And how has this impacted the cousin's relationship with her, if at all?

10:11We don't really know yet because this was pretty recent. This was like right at the end of August. We haven't seen the family since then. So I don't think we're going to be invited to their wedding. But we'll see them at Christmas probably. If you get invited to the wedding, I beg you to wrap up all those cat toys and make that the present. Or just a note that says we're even. Yeah, we're even. Yeah, I was going to give you$3.40, but we're even. That's a great idea. I did think a lot about the psychology of it, especially as a nurse. I was like, there's something else going on here. There's no way in hell she thought that was OK.

10:46Right. Because like this wasn't even like a teenager. This is like a 22 year old. Now, let me ask you this. Is she from a well-to-do family? Is she used to like when she went anywhere, she got whatever she wanted, maybe? We ran through all these scenarios, too. Where did she get the idea that this would have been OK? Did she nanny for somebody before that this was just normal? But we never really got to the bottom of it. because nobody was really like giving us any information about her. This is such a stupid story. Right? That's like the adjective that best describes it. It's like so stupid. Why'd she do that?

11:19Day one. Yeah. No, people didn't believe us. They were like, this one only happened to you guys. Like, I know. Oh, well, Stephanie, that's delightful for us and not for you. It's so nice meeting you. Yes, you too. I just have to have a quick shout out to my bestie, Shanna, because we're arm cherries together. Heather, we went to your Portland show. She has been my bestie since I was four years old. She was a first gal at my birthday party and probably one of the last. And we're headed to Vegas in two days with our awesome group of friends. Isn't a lifetime best friend literally the greatest gift a human can receive?

11:52They're the best. Yeah. Let's go to Vegas then. Let's meet them in Vegas. Yep, we'll be there on Friday for her husband Bass's 40th birthday. Happy birthday, Bass. Bass, shout out. We'll stop there en route to our boyfriend trip to North Carolina. I could stop, but you would really be going out of your way. All right. Well, lovely meeting you, Stephanie. Thank you, you too. It was nice to meet both of you. Thank you. Take care. Bye. Kate. Hi. How are you? I'm great. How are you today? Good. We have a surprise for you, best friend. Aaron Weekly is here. Hello, Aaron Weekly. How are you? Hi. I'm filling in today.

12:27Oh, I hope Monica's okay. I'm here in a professional capacity. Yes. There's nothing fun about what he's doing. I mean, it's all business. She's healthy. She's just attending a family function. We thought the next best thing would definitely be Erin. I agree. Kate, where are you in the country? So I live in Nashville. However, I'm in Indiana for work right now. So my hotel room has become the best sport I can make. Sitting on the floor. I am. Yeah, okay. And it looks so much like a hotel. I knew you were in a hotel room because they have a weird size pillow that only exists in a hotel room. It's not a long one or a short one.

13:03It's in the middle. And why do they try to sell them? Because nobody wants that size pillow for their home. I think it's that they made them, no one bought them. They're like, well, let's dump them at the hotels. These are pretty thin, too. They look a lot fluffier than they are. So I don't know how great of a sleep I'll get tonight, but that's OK. OK, so you're a Nashvillian, Nashvillian. I don't know what we call ourselves, actually. I've been there about seven and a half years. Where did you move from? I'm an army brat. I've lived all over the country, but I moved from Los Angeles to Nashville.

13:28Similar trajectory. I've heard that story before. OK, so you have a babysitting story. I do. Grew up on the West Coast and my father retired there. I was about 10 years old and we moved into a neighborhood with a lot of other formal military people. Ended up moving next door to a couple from England of all places. And they had three perfect, beautiful blonde baby girls who just had the cutest little accents. I was about 10 or 11 and wanted to make some money on the side. So started babysitting for them. The news spread that me and two of my best friends that we all babysat. Next thing you know, we're babysitting for seven or eight families.

14:04It's a real business. 10 to 12. It's great. Yes, yes. So they end up selling their house a couple years later and moving into a larger home. They just outgrew their space and it was across town. And when they moved there, they moved into kind of a secluded area and their next closest neighbors were about two or three blocks away. And they ended up becoming friends with them. And next thing you know, I'm babysitting for both the families. So the three little girls and now this next family that has one daughter. Sometimes it's all four. Sometimes I'm doing one or the other family. And we get to a point where I become friendly with this new family, find out the dad has gone back to college to get his teaching certificate and would like to start teaching math.

14:44My mom decides, hey, you need a math tutor because you're not great. So why don't we see if this gentleman can start tutoring you? So he does while he's getting his practicum hours and I'm babysitting his daughter a couple times a month and twice a week I'm getting dropped off at his house. He's tutoring me and then he's driving me home. And this goes on for about, I don't know, six, eight months. Super nice guy. Sometimes the daughter and the wife are home when he's tutoring me. Sometimes they're not. One day my mom gets a phone call from the wife and it is, hi, Shelly, so-and-so can no longer tutor your daughter.

15:21And my mom goes, I'm sorry to hear that. What's going on? Well, he is having some mental health issues and he just needs to take a step back. And my mom said, I'm really sorry to hear that. And she knows that my mom's father experienced mental health issues and ended up unfortunately passing away from them. And so she was asking my mom for some help. And my mom said, I can be here for you emotionally, but I'm not equipped to give you any advice. Yes. Yes. That's kind of the last we hear from them for a while. So I'm still babysitting for the English family during this time. And they're not really seeing this family either.

15:54They said, And I think the mental health issues just are wreaking havoc on the whole family until they've stepped back.

16:16Fast forward another year, I'm still kind of babysitting for the English family, but they've gotten older. They're in school full time and it's just not as much. and my dad hears or is reading the newspaper and sees an article that the father who had the mental health crisis had been hired to work at a local high school and he had been fired and the details were very vague something happened that was inappropriate but not a whole lot of information behind that we kind of all said wow that's too bad mental health issues must still be continuing and we left it at that. Next thing you hear from the English family, the wife has left the man who is having a mental health crisis.

16:57So we then start to put together, okay, maybe something more nefarious happened than originally thought. Maybe the mental health issue is pedophilia. Yeah, I was going to say, I do not like where this is going. I didn't like it from the getting driven home. I started getting scared. So after that, we just don't really hear anything. The wife and daughter move into a new place. We hear that the dad moves into an apartment. And mom is the word for about a year. I am now going into my senior year of high school. I can finally drive myself to get things. So drive myself to Target to pick up my school supplies.

17:31And you know how all Targets have the very long walkway that you can see the door all the way to the end until you turn. Walking down there, I'm 17, just in my own world, and physically run into a man. And I'm so sorry. I look up. It is the father. I'm like, oh my gosh, how are you? And he's not looking at me. He's looking everywhere but me. He's fidgety. He's holding a shopping basket. How's your daughter? He's fine. How's your wife? And he's like, oh, fine. And I kind of pause and he looks up, makes direct eye contact with me, drops his basket and runs out the front door. Oh my goodness. What just happened?

18:13So I go about my shopping. I go home. obviously tell my mom I ran into him she said wow I guess he really never got the help that he needed it's really sad to hear this is still happening so the next day my mom and I will remember this till the day I die was cleaning our downstairs bathroom a little half bath and my best friend's mom called and no pleasantries get your mother and I'm like uh she's the middle of something she's like I don't care get your mother right now I walk into the bathroom mom someone wants to talk to you. The friend says, are you sitting down? My mom says, no. She said, please sit down.

18:48Oh, really quick. I wish someone would say that to me once in real life. I see it in movies all the time. Please sit down. Yeah, like, do people faint that much that it's really necessary? Did your mom sit on the toilet? Yeah, no, we were in the living room at this point. Oh, okay. I think it was more like she was worried what my mom's reaction was going to be. And so she was like, if you're sitting down, we minimize. Are your hands handcuffed to something firm? Cover your ears. Cover your ears, I have something to tell you. She proceeds to say, Mr. So-and-so was arrested today. And my mom says, wow, that's bizarre.

19:23Kate ran into them yesterday and saw them, and it was a really awkward interaction. And the friend says, well, do you remember that 16-year-old girl they found stabbed to death on the walking trail three weeks ago? Oh, no. He's the one who did it. He had kept the knife and the bloody clothing. and so they found it when they went to arrest him. Oh my God, he murdered a girl? Shit. My mom proceeded to get up, walked right to the bathroom she had just cleaned, threw up. Okay, so she did need to be warned. She did. Although the French has said, do you have a bucket closed to you? How much can you prep someone?

20:00I have something to tell you. So what we found out is that he had met a 16-year-old on a chat room. She was about three and a half hours away. He bought her a bus ticket to come down. They started a relationship. The daughter that I had babysat for had met this girl. Apparently the girl tried to leave. And in that moment, he figured, oh, I'm probably going to get in trouble for this. And it was a crime of passion. And the daughter covered for him when the cops came around the first time and said, I've never seen that person before. Oh, no. It was very sad. Needless to say, my parents sat me down for about two weeks peppering me.

20:39Did anything ever happen? Yeah, yeah, yeah. I called my best friend today to recap all of this. And she said he was the nicest dad we ever babysat for. Not creepy. We had a couple of creepies, but never would have guessed that the man I used to babysit for killed a girl my age. And I saw him the day before he was arrested. Oh, my God. But obviously, he also had something cooking with one of the students when he was working there and he was a pedophile. Yeah. What's really crazy about the whole thing? He only got 20 years. So he got out last August. No way. Jesus. He's out. What state? I'll just say the Pacific Northwest.

21:14Okay. They breed them there. Yeah. There's something happening up there. Whoa. You never know who's next to you. You don't. And I think we all would love to believe we could somehow smell that out. And we can't. I also think there's a fine line between sane and insane. And it takes something very simple to push that. I wonder what mom discovered back in this. She can no longer be tutored. Like, I wonder if she had already found some weird stuff on computers or something and said, I got to keep him away from young girls. Unfortunately, they changed their name and moved. We've never heard from them.

21:46Nobody's been able to contact them. We always wanted to check in on them. And they were such a kind Christian family. I'm sure it just wreaked havoc. They didn't feel that they were comfortable in their communities anymore. So very sad. Oh, my Lord. But you dodged a big bullet. We had a babysitter that went on to kill. Aaron, do you remember Leslie? Of course. That's who babysit you and David at the apartment. Yeah, which is an exaggeration. He didn't do the babysitting, but he was dating our babysitter and he had come over to the house. You guys got something in common there. You don't bump into a lot of people whose babysitters murdered people.

22:18Hey, we got out the other side. So I guess it's a good story to tell. And I got to tell it to you guys. Did you just have a war chest of money by the time you graduated? That's a lot of babysitting. Were you like rolling in dough? You know, I wish I was. I unfortunately have a bit of a shopping habit. So I just had really nice clothes growing up. That's Aaron's policy. Yeah. Now you guys have something in common. Yeah. Enjoy today because there might not be tomorrow. I mean, that's what I learned from this situation. My therapist asked me that. Like, what did you learn from this? And I said, I have a lot of empathy and you never know what tomorrow brings.

22:51So you better have fun today. Well, lovely meeting you, Kate. Thanks for taking the time on your Indiana trip. Thank you. I do have to have one shout out to my friend Megan because she would kill me. She is the person who says every prompt that you guys put out, I could tell a story for. And so she encouraged me to say this and we text each other every week on all the episodes we listen to. And she's my arm, Sherry, with you guys. Oh, shout out, Megan. Thank you, Megan. I appreciate it. And send our love to Monica. Okay. Bye-bye. Murder. We weren't expecting murder and babysitting. It was not.

23:25No. It's a little better than what I thought was. Yeah, weirdly. Better than pedophilia? I mean, isn't that weird? Yeah. But wasn't he both? In this case, he was both. That's true, yeah. I guess it wasn't better. No. But would you agree you would way rather hang with a murderer? Absolutely. Did you do any babysitting? I did a little bit. I would have loved that source of money. I think the thing I'd love most about being a babysitter is going into people's houses and them having snacks. Neither of us had shit for snacks. Right. No, that would have been great. No, I never did. You remember my craziest story is that I babysat a kid that was my age, but my dad made me lie and say I was older.

Read the full transcript

24:05but it was in Walled Lake. So like I would go babysit this kid and his sister and my dad and his buddy would go out to the bar all night. No one was ever going to know this, of course. But then I moved to his house in ninth grade and I get into my fucking homeroom and I'm in a homeroom with this kid who thought I was two years older. And I just remember feeling so embarrassed for him. Like, oh Jesus. But it never seemed like he put together those pieces. Maybe he didn't. The gap was staggering. He was like a kid and I was an adult. or it really felt like appropriate that I would be babysitting this kid and his little sister.

24:39They'd be fighting and stuff like kids. I'd be like, okay, no. Jeff. Hi, how are you? I'm great. How are you? Good. This is best friend Aaron Weekly. Monica is out. Hi, Jeff. Crazy enough, I'm in Kalamata, Greece at a friend's house on vacation. Oh, lucky you. What's the scene in Greece right now? It's been amazing. We flew into Athens and we have some friends who are Greek and they've been touring us around. So we've been here for about five days. So it's like 1130 at night here in a small house. I got everybody sort of out of the room so I could do this. Thank them for us. I'm here mostly because my daughter's just a huge fan of you guys.

25:17As soon as she saw that the prompt was babysitting, she called, she's like, you got to go online and tell your babysitting stories. I was going to ask you, is this a wife or a daughter who listens to the show? I was going to maybe guess that without offending you, but this makes total sense. I must say, I listened to a whole bunch today and it's awesome. I really enjoy the show. And my story is old enough that hopefully the references won't be lost on anybody. Okay, great. Well, I doubt you're that much older than me, so I bet I'll get most of them. So hit us with the babysitting story. This is set back in the early 80s.

25:46I was 16 years old. And my mom, who was one of these super caring, loving, nice to everybody people, came home from work one day and she said, I volunteered you for something. And she did this a lot. Where did you grow up? I grew up in London, Ontario, a couple hours out of Toronto. I tell this to everyone from London, Ontario. So I grew up in the 80s in Detroit. And once a year, we would take a road trip to Toronto. And we would always immediately get McDonald's in Windsor when we crossed the border. And always around London, Ontario, we would finish our big McDonald's and just shove it out the window, as everyone did in the 80s.

26:20So I always apologize to anyone from London. They probably got a bunch of our McDonald's trash. A lot of litter on the 401. She was talking to a guy she worked with, a really nice guy who was a single dad, had gone through kind of a messy divorce and had a son on his own. And he couldn't get a babysitter because being a single dad, he said all the babysitters needed a ride home. And he said, of course, I can't drive them home because I have to stay home with my son. So he just sort of gave up on going out. He wasn't dating. And I said, well, I'll get my son to babysit for you. He's got his own car.

26:50I was 16 at the time. I had a sister, Sue, who she babysat, but I didn't babysit. I'd never done it before. I knew nothing about kids. So I had zero interest in babysitting. But of course, it was too late because my mom had volunteered me and she was selling me on it. She's like, it's really easy. He's going to have you arrive late. His son, whose name is Andrew, will be in bed. And he's like, you just have to go in, watch TV, eat snacks, take care of the kid until around midnight. And then Tom will get home and you can leave. So it did sound like a pretty easy gig, even though I would have rather been out with my friends on a Saturday night.

27:20I went to this guy, Tom's house, which I was meeting for the first time. I pulled up in my car. He had this old house in the old part of London, creaky stairs, creaky floors. I went in there and he gave me the tour. He showed me the snacks and then off he went. How old was the kid sleeping? I think he was three. Oh, that's pretty young. I can honestly say that I've never seen this kid. I didn't that night and I never have since. I never got a look at him because he was locked away and that wasn't my responsibility. So I flipped on the TV. I did what any 16 year old would do first. I snooped around his house a little bit.

27:52cords, checked out what he had, then grabbed some food, laid down on the couch. I was a big Saturday Night Live fan. I think those are back in the Eddie Murphy day. So I probably watched Saturday Night Live and just quickly fell sound asleep. Good nap on the couch until I heard the door open and he said, thank you so much. This was amazing. And he paid me and I got in my car and I drove home and driving home, I go, this wasn't that bad. Maybe I'll do more babysitting. It was easy money. I just ate pizza, watched TV. Rifled through his drawers and then went home. Exactly. I pull onto my street and at the end of my driveway, there's like a crazy person.

28:29And it's my mom. She's got her fists clenched and she's just freaking out. And of course, I'm like, I'm just arriving home. I'm like, oh my God, what's going on? And I pull into the driveway and she's screaming like, where is he? Where is he? Oh no. Where is who? And she's like, where is Andrew? And I'm like, I don't know. She's like, well, he's not there. Tom's been calling and he can't find his son. Oh my God. I was like, I never saw the kid. I didn't go upstairs. I had no idea where the son was. And then part of me probably at the time is thinking like, I've been set up. This guy is like a murderer and he's going to put it on the babysitter.

29:06Yeah, yeah, yeah. Because I never checked if the kid was even there.

29:25it turns out after a couple phone calls and me saying i don't know and i'm saying to mom should i go back and he's saying don't come back there's nothing you can do he kind of had an inkling and it turned out he had an estranged ex-wife she had some mental issues and was not allowed to see her son. And she had snuck in while I was sleeping on the couch and took the kid up the squeaky stairs, grabbed the crying three-year-old back down the squeaky stairs, passed the sleeping babysitter. And I just slept through the whole thing. You're useless. You might as well not have anyone there. Exactly. You're only hiring him in hopes that in case there's a kidnapping, you could intervene, but no.

30:03He sort of figures out that it was probably her. And he has a sister who's also in London. She doesn't even live in London, his ex-wife. She's in some other city, probably in Windsor near the McDonald's. I hear this in court, I'll tell you the rest of that story. But he heads over to the sister's house, hears his son crying inside, knocks on the door, and when they don't answer the door, he kicks down the door, apparently punches the sister's boyfriend in the face, grabs his son, gets back in the car, and drives home. So he's got his kid back, and you'd think everything's okay, but he gets charged with assault.

30:36I end up being a witness in the case, a pretty useless witness. I really don't know why I was there, but I had to go to court. And this was maybe a month later. And my mom takes me and we go to court and we sit outside and his lawyer's briefing me like, here's what you need to say. His lawyer's trying to say that this woman violated her order and stole her kid. He's trying to get her charged with kidnapping and instead he's being charged with assault. And so I have to go up and testify. And of course the judge just makes a fool. Everybody makes a fool of me. Like, so did you go upstairs? No, I didn't go upstairs.

31:07Did you see the kid? you remember anything you should have said who's on trial here yeah were you doing drugs or alcohol i was like i was not doing drugs and alcohol i was just sleeping i looked for drugs and alcohol everywhere but i couldn't find anything so that was one of my more embarrassing days of my life that's weirdly better than what i was gonna guess the thing that seemed most logical to me is this boy who had not been introduced to you before he went to sleep he just wakes up in the middle of night to get a drink of water and there's a fucking strange dude sleeping on the couch and his dad's nowhere to be found.

31:39So he runs like I would get the hell out of the apartment. Equally plausible story based on how sound I was sleeping. The funniest part of the whole story is this all ends and it kind of goes away. I'm going on with my life and I'm 17. A year later, my mom comes home from work and she's like, Hey, Tom was just wondering, like, would you be interested in babysitting again? I politely said no. And until I was parenting my own child, that was the only time I ever babysat. Tom's nuts. I mean, I would not hire you again. I left some uppers for Jeff on my nightstand, which I'm sure he'll be going through.

32:12So just tell him that there's some dexedrine there, see if he can keep his eyes open this time. Exactly. Oh, well, Jeff, thanks for taking time out of this great Greek vacation. No problem. Thanks so much for having me on. I got to make a shout out to my daughter, Andy, who, like I said, is a massive fan of you guys. Send our love to Andy. Okay, take care, Jeff. That's so great. that he had to go to court for being a witness. He's like, I don't know. I don't know. Ask someone else. Hi, Macy. Hi. Where are you at, Macy? What part of the world? I am currently in San Jose, so just north of you. But this story takes place in Toronto.

32:49I'm originally from Toronto. Can I blow your mind? Our last caller, Jeff, was telling us a story from London, Ontario. Close by. So you were born and raised in Toronto, but now have relocated? Yes. I just moved here three weeks ago, actually, with my partner. Okay. What brought you to San Jose? A job? His job. Is he an athlete for the Sharks? No, he's not. Oh, look at this. No, he's not. Well, of course, they're from Canada. But wait, this is nuts. The person who said that was Sharks. He's with them right now, but he's in between teams. So we'll see if he makes it. Okay. You would know this player.

33:23He played for the Maple Leafs, Fanuc. What is it, Rob? Dion Fanuc. Dion Fanuc. Do you know that player? I don't know much about hockey. I'm just the supporter. The hockey wives is a whole thing, right? That's like a whole scene. It is. I've worked with an actress who was married to him. And the first time he came in to visit the set, and I knew he was coming from practice, I thought, oh, this is so weird. Dion left his pads on. Like, he left his pads on under. I really thought that. That was the only explanation I could have for how fucking big his haunches were. And then once I saw it, I was like, Dion, you have the biggest ass I've ever seen.

33:58I thought you had your pads on. I know. It honestly blows my mind every day too. And how long have you been together? Three years. Three years. Did you mean in high school? We did. This is fun and lovely. Okay, so you have a babysitting story. Do I ever? It was December 20th of 2023. And I was 19 years old caring for a family of four. And they're seriously like family to me. I treated them like my own. I still do. I love them like my own. and at the time they were six months old, two years old, four years old, and seven years old. So Macy, that's a lot on your plate. Like I think the parents can barely handle that.

34:34That's why I'm there. They're the best kids in the world, honestly. Like I wouldn't babysit for them if they weren't. I'm quite strict with who I babysit for, but I was there two, three, four times a week helping with everything from date nights to afterschool activities. I was always their go-to gal. But this evening, the parents had left around 5.30 for dinner and a Raptors game, so basketball. And I followed our usual routine. I put the first baby down around 6, the 2-year-old down around 7, and then the older two around 8, 8.15. So by 9, all kids are ready for bed, sleeping, books read, teeth brushed, pajamas on.

35:11And really quick, we were just discussing this. Did you love the snacks that were available at this house? Is it now snack time? It is. That is my next point is I went downstairs. I had a snack. How much rummaging did you do? I don't do too much. We did some exploring. We went to every room. Yeah, we're bad. I watched some TV, FaceTime my boyfriend. At this point, it was around 11 and my boyfriend had gone to bed and my phone had died. So I went to sit at the kitchen counter to charge it. And the kitchen island's near the back door. and I heard some rustling in the backyard and I assumed it was like raccoon or a squirrel, just normal nighttime activity.

35:51Though such noises always make me a little uneasy if I don't know what it is. But then I heard footsteps coming up the back porch. Okay, and raccoons do not wear shoes. And can I ask, is this in a residential area or is this downtown Toronto? This is the residential area. So they had a house and a yard. So my first thought was that the parents had come home, but it was odd because they've never gone through the back door. They always use the front door. And I turned around and the sliding door began to open. Oh, no. And a man who I've never seen before peeks his head inside. And he's mid-30s, scruffy, maybe 5 '7", 150 pounds.

36:32So he's not a big guy. But when our eyes met, he didn't stop. He decided to fully step into the house and close the door behind him. Oh, my goodness. Oh, my goodness. In that moment, my guard was up, but also I was quite calm and just trying to put the pieces together. And his confidence was so high. It was like a neighbor maybe or something? Yeah, he was a neighbor. He knew the parents, but quickly reality set in. And I was like, this man does not belong in this house. So I stood up and I approached him. And instantly his response was, get down. I'm hiding from somebody. Shouldn't you get down, sir?

37:05If you're hiding, why would I hide? Wait, who's getting down? We both are. And before I could react any further and push him outside, he grabbed my wrist with the strongest grip I have ever felt in my life. And he just began dragging me through the house, trying to turn on all the lights. He was kind of on his hands and knees almost while still holding on to me, like hiding. And their main floor was quite large. So we were just doing circles through the kitchen, the living room, the dining room. And I was trying so hard to yank my arm away, but nothing. He would not budge. I'm imagining, too, you probably don't want to scream because you don't want to wake up the kids and get them involved in this.

37:45Yeah. So I'm trying to be quiet, but also figure out what's going on. He's looking through windows, turning off the lights, and he's very frantic. And with my free hand, I managed to grab my phone and start calling 911. Wow. Good job. They didn't answer me. No. They went to voicemail. What? They have voicemail at 911? Not a great job on their end. He noticed immediately and he snatched my phone and he threw it across the room. So now it was just me versus him. Oh my goodness. And he continued dragging me through the house. And he just kept repeating, like, I'm hiding from somebody. I'm hiding from somebody.

38:20And my mind was thinking three things. One, if he actually is hiding from somebody, I can't deal with two people, let alone if this person has a weapon, I'm done. Yeah. Two, he could not go upstairs to those children. He can't even know there's people upstairs. And three, I knew that if this were to go south, more south than it already is, that the parents were going to be home within the next 15, 20 minutes. So I just needed to fight, I guess, for that long. You're so level-headed. Did you grow up in a lot of chaos? I mean, I'm one of four. But you're like shockingly level-headed. You're 19 at the time.

38:50I'm impressed. Yeah, so he's dragged me to the front of the house. And like I said, it was December. So it was Christmas time. And they had a beautiful nine-foot tree with all their best ornaments, the best lights. It's like it was such a show tree for the front foyer. I want to be in this family. Like a good snack. They sound loaded. Feel so safe with Macy babysitting. Yeah. All of that shattered as he throws me into the tree. Oh, fuck. We're now wrestling. So I throw him. He throws me. He still has my arm. So I'm just one-handing it. What felt like an eternity was probably only a few seconds, but I knew that this wasn't supposed to be happening.

39:27And shock kind of set in that. I'm like, I got to get free. I got to get out of this. so we were wrestling so hard that he now threw me to the ground he was straddled on top of me he had been pinned down and I had no way out oh I looked over and I could see my phone ringing from an unknown number I'm like oh the police is calling me back I felt like it was kind of now or never to get into the situation and go grab my phone so I just started fighting back and I just began punching him as hard as I could in the head that wasn't really working because I was just going for the skull and not any part of his face that could possibly hurt him he wasn't even flinching I'm going to blame it on the angle.

40:01And now you know what your boyfriend deals with. You get that shirt over the back of the head and go to town. He's a fighter too. So maybe learn a few things. When that wasn't working, I remembered the only self-defense advice that I was ever given as a kid. So with all of my force, I kicked him three times where I knew it would hurt him the most. In his testicles? Yes. It worked. It worked. He collapsed immediately in so much pain, finally releasing his grip. So I went and I grabbed my phone. I called 911 back. What a surprise. They didn't answer me again. Jesus fucking Christ, Toronto 911. Get it together.

40:34Was your missed call 911? No, it was. I had like five missed calls from them. What if you left a message and you go like, hey, we're playing a little bit of phone tag here, but I do have a guy in the house that's trying to kill me. I probably bought myself nine seconds. You think you could get back to me in that window? Yeah, but I knew that they would call back eventually. So at this point, he was still hurtled in a ball and I was kind of in charge now. So I just began shouting back at him like, what are you doing? Why are you here? And I raised my phone and I took a photo of him. I knew that I needed evidence and I was aware that I was in shock and this was a crazy situation.

41:11And if he'd managed to get away that I would be no use in giving any description. So I made sure to get the photo. And at the time, it seemed like the smartest option. But 911 wanted to call me back. He now stumbled to the side door. And the side door led to the basement. So he was still trying to convince me to come hide with him, come to the basement with me. And obviously, I refused. I was like, I backed away. I refused to go near him. And the officer on the phone had told me to go to the front porch to see if I could hear sirens. And I did so that I knew that the cops were going to be there shortly.

41:43But when I went back to the side door, he was gone. And so the police arrived very quickly. They made up for their lackluster performance on the phone. Yeah. And four cars with their lights on, like rolled up onto the curb, guns drawn, shouting like, please put your arms up. Honestly, that was the most terrifying part. I've like never experienced that before. And I'd warned them over the phone. I said, I didn't know if he'd gone to the basement or if he'd gone out the side door. So they searched the basement, but he wasn't there. And shortly after the police showed up, I'd ran upstairs to check on the kids just to make sure everybody was still in their bed okay.

42:17And the oldest daughter was awake sitting in her bed. She said, what was all that noise? And I was like, oh, you know, there was just some people outside being really loud, but they all went home now. She goes, but there was a lot of yelling, like I'm scared. Where's mom and dad? And I said, they're going to be home so soon and give you all the huggies and the kissies, but you're safe, but you need to go asleep. So when they get home, they won't be mad at you. And that worked all the time. So we tucked her back into bed. I ran downstairs to see if the parents had come home and they returned shortly after that, stunned at what have happened to their house.

42:49My tree.

42:54As soon as I saw the mom, I just started bawling my eyes out and I was like, somebody broke in and attacked me, but everything's okay. Everyone's okay. When it all settled down, I gave the police a statement. I called my mom to come pick me up. Even though I had a car, I could not drive home. And she ended up sleeping with me in bed that night and they didn't end up catching him and he got away on foot that night. So I just went along with my life for a few weeks, but the story does not end there. Two weeks later, I got a call from the police saying that they'd captured this guy and they need me to come down and identify him.

43:24And I was like, yeah, of course, I'll be there tomorrow. That night, a news article came out with a mugshot of the guy and said that he'd been arrested and charged with sexual assault because he locked a woman in a bathroom with him. Whoa. And I don't know what else happened. But thanks to the photo I took, I was able to identify him, leading us to go to court six months after that. So we went to court. I testified. He testified. We were cross-examined. New information came up about the case. So we had to come back a whole two months later for another day of court. Long story short, he ended up being found not guilty.

44:00What? Due to what the court thought was insufficient proof. Oh, my Lord. He remains a free man and he is out in this world doing who knows what. He does have a criminal record that is three pages long and they still don't seem to take into account that he's not the best guy you want running around town, yet they still won't do anything about it. Did you get a sense when he was on trial and you were in the courtroom with him, did he seem mentally not with it or did he seem with it? He was not with it. he just wouldn't answer any question anybody was giving to him. And he just claimed the whole time that it wasn't him.

44:40It's not the best ending to the story. But I mean, I did learn a lot about myself that night. Fuck yeah, I'm so proud of you. Can I look now at these photos? Oh, yes. I took a photo of him. Oh boy. He looks like a creature from Lord of the Rings, if I'm being honest. It looks like you trapped him in one of those nets. Yeah. It also looks like he's holding a toy soldier or something. He's like reaching his hand out at me. What's the other photo we're looking at? So the other photo is my sweater and his handprint and how dirty he was. He is dirty, isn't he? It looks like he crawled out of a tunnel.

45:17And yeah, his hands would support that. I mean, see, that's terrifying. Have you had, I'm not going to be serious. Have you had like residual kind of PTSD? Are you like triple fucking checking the locks all the time? And do you have a Lady Remington in your purse? obviously it was traumatic but what are the odds it's going to happen to me again knock on wood but still like the door could have been locked and i could have prevented that from happening i do triple check the locks well you would think the logical part of your brain would be like right it happened once odds of it happening again are in the bazillions to one but i would say that your worldview changes as reality changes so it's like oh that happened once that can happen you pretty much don't think that can happen until it happens it was my biggest fear my house being broken into.

46:01So if I can overcome that, I think I'll be okay. Now, what about this big gorilla you're hooked up with? Does he not want to find this guy and pulverize him? We were doing long distance at the time. So I texted him that night and I was like, somebody broke into the house and assaulted me, but I'm okay. I'm safe. And that's all he's got. So then in the morning, he was freaking out and he was like driving to my house that morning. I mean, it all has passed now. It's all good, but he is a protector and I appreciate that. And it turns out you're a protector as well. You have four kids upstairs. Yeah.

46:36Well, Macy, that's a crazy story. I'm so glad you told it to us. Thank you for having me. Actually, the day after it happened, my mom was like, this would be such a good anonymous story. Oh, she did. Well, just immediately the next day. No, it was the first thing we thought. Oh, wow. I feel very flattered by that. Very thin silver lining, but I'll take it. Thank you, Macy. Thanks for everything you guys do. We appreciate it. Our pleasure. Bye, guys. Bye. Half of our babysitting stories involve people entering the house. I'm thinking about maybe double-checking my luck. Well, I love you. I'm so glad we got to do this together.

47:12Yeah, I love you too. That was fun. Thanks for inviting me. Do you want to sing a tune or something? I don't have a theme song. Oh. Okay, great. We don't have a song for this new show, so here I go, go, go. We're going to ask some random questions, and with the help of Armchairies, we'll get some suggestions. On the flyer, I'm Dish. On the flyer, I'm Dish. Enjoy. Follow Armchair Expert on the Wondry app, Amazon Music, or wherever you get your podcasts. You can listen to every episode of Armchair Expert early and ad-free right now by joining Wondery Plus in the Wondery app or on Apple Podcasts.

48:00Before you go, tell us about yourself by completing a short survey at wondery.com slash survey.

From the publisher

Dax and Monica talk to Armcherries! In today's episode, Armcherries tell us about a bad babysitting experience.

Follow Armchair Expert on the Wondery App or wherever you get your podcasts. Watch new content on YouTube or listen to Armchair Expert early and ad-free by joining Wondery+ in the Wondery App, Apple Podcasts, or Spotify. Start your free trial by visiting wondery.com/links/armchair-expert-with-dax-shepard/ now.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

More from Armchair Expert with Dax Shepard

All 296 episodes
Armchair Anonymous: Babysitting IIArmchair Expert with Dax Shepard · 48 min
Listen in VO