Boy (7) Makes Five Babysitters Quit So Mom Records Number Six And Discovers Why

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Madeline couldn't understand, she had gone through five babysitters in six months with each of them never lasting very long. What was going on? What was wrong with these babysitters? She knew if she wanted to figure out the problem, she'd have to be rather shrewd and sneaky.

Anything for her children, after all. 

Getting answers


Madeline opened her laptop to look at the footage she filmed of her new babysitter. The first time she tried to film it didn’t record. But now she was getting the answers. For months she wondered why the babysitters all left after a month. But finally she was going to get the answer she was desperately looking for.

She saw it

Every month a babysitter left Benjamin and every time a lot of drama was happening. She decided to find out what could have happened. She opened it and there she saw it. Finally, after all these months Madeline understood why they all left Benjamin. 

What is wrong with her son?

She could barely look Benjamin in the eyes. She couldn’t understand why Benjamin behaved this way. How could he do this without her knowing? She had the feeling that she didn’t know her son anymore. 

What was wrong with her son? Why didn’t she know this earlier? And why didn’t the babysitters tell her about Benjamin?

Carrying him late

Madeline had her son Benjamin at 25, and to say he was a surprise would be an understatement. She found out she was carrying him pretty late, and by then she did not have the contact information for the man who she assumed to be his father. It was a one-night stand! She never would have thought she’d get pregnant from it.

Young and Having No Fun

Madeline’s parents lived about thirty minutes away, so for the first couple of years, she had some help here and there. But her father wanted to retire, and by Benjamin’s third birthday she was all alone in the city. It was difficult, but she made it work the best she could. She didn’t have a choice.

Nobody There to Care

She worked part-time doing real estate for a well-established firm in the city, and it paid well enough to where she and her son were able to live comfortably. However, even this was a significant amount of time to spend away from her son. Childcare options were limited, and her only choice was one she had been avoiding making.

Admitting Defeat

It was time to find a babysitter for Benjamin. This was something she didn’t want to do. She wanted to do her very best to be there for Benjamin as much as possible, and she didn’t believe in letting other people raise her kid. It was important for her to instill in Benjamin the same morals she grew up with. She had to work though, so unfortunately she would have to compromise on this one.

Too Many Choices

There were plenty of babysitters around, but the difficult part was narrowing them down. She went through tons of interviews, and it was exhausting after a while. She went through agencies and independent babysitters, and she had to admit, her nerves were making it harder than it should have been.

What Do You Prefer?

Since Benjamin was six, she wanted to hear his input on all the choices. He was generally quite shy in front of strangers, and he didn’t like being away from his mother for too long. He was a clingy baby that grew into a very needy child, and it made him upset that she was going to be around less. He couldn’t understand why she had chosen a job over staying home with him.

Mistrial No. 1

One afternoon, when Madeline had returned for work, she encountered a tearful Denise, who resigned from her position hastily and without explanation. Madeline attempted to ask Benjamin what had happened that day, but he merely shrugged and continued to play, insisting she join him. What could have possibly made her react in such as way?

One More Time

Madeline decided to give the whole babysitter thing a second chance. She went with another woman, hoping Benjamin would find comfort in someone that reminded him of her. But it just didn’t work. This babysitter had quit with a brief, yet hostile text the next morning. One more, Madeline questioned Benjamin about his day. He shrugged again, swearing on his teddy bear he’d done nothing wrong.

I Need a Hero!

In an attempt to appeal to Benjamin’s boyish sensibilities, she hired a man named Aidan as his third caretaker. Benjamin latched on to him quickly, and it was very clear he had great admiration for it. Three weeks went by without issue, and Madeline was starting to feel less anxious whenever she left for work.

Moving On

On the second day of the fifth week, Benjamin had lost out on his third babysitter. Aidan had informed them he had been offered a full-time job, so he didn’t have the time to watch him anymore. He promised to stay for a month to give Madeline time to find a new sitter. Benjamin was heartbroken, and it certainly showed.

Way Beyond Mad

Benjamin’s obvious fury must have been too much for Aidan because by the middle of the following week, he was gone. Madeline recalled their last conversation to be full of frustration on Aidan’s part. He recommended that Benjamin should be socialized around other children, and perhaps a professional teacher would be more suitable for him at this age.

Running Out of Options

Madeline couldn’t believe her horrible luck. Daycare was incredibly expensive, and it was quite far from where she worked. It would be a hassle to lug Benjamin to school and head over to the brokerage across the city most of the week. She contacted the babysitting agency and begged for another sitter, but they refused. Their employees simply had too many unpleasant experiences in her home.

Sorry, You're Out of Luck

The company did not relay any specifics to Madeline, but it was hard for her to come to the terms with the fact that perhaps this was all due to Benjamin’s behavior. He was nothing but a sweet, perfect boy with her around. She couldn’t imagine him misbehaving to any degree.

Hoping for a Miracle

Keeping her faith, she contacted another babysitting agency, which sent out a total of two more babysitters to her house. It was no use. One after the other lasted no more than a couple weeks and looked visibly haggard at the end of their time caring for Benjamin. They wanted nothing to do with him.

Her Last Chance

Madeline was on the verge of giving up. If she wasn’t able to find proper child care, she would either have to move across the state with her parents or give up the job she loved. After a long and thorough online search, Madeline was able to find her sixth babysitter. The woman’s name was Brooklyn, and luckily she had experience working as a teacher for young children.

Born to be Besties

When Brooklyn and Benjamin were first introduced, they immediately clicked. Madeline didn’t want to get her hopes up. She had seen this so many times before that it was hard for her to stay positive about it. She prayed Brooklyn would be able to last much longer than a month.

Getting to the Bottom

She couldn’t understand why the last babysitters had refused to give her any real information about the activity leading up to their resignation. She refused to stay in the dark any longer about it. Before Brooklyn began her first day, Madeline installed small cameras around her house so she could have a live view of Brooklyn’s day without anybody knowing.

Making Her Own Rules

Madeline understood that filming her son and babysitter behind their backs wasn’t exactly the best look for her, but she was running out of options! She needed to figure out what was going on in her home when she wasn’t there, and she wasn’t getting answers the traditional way. It was time to step it up.

Almost Giving Up

Embarrassment was starting to creep up on Madeline. It did not seem like any other mother was having nearly as much trouble in the babysitter department. Her mom friends all had lovely long-term nannies that developed wonderful relationships with her children. She felt out of place that nobody was a perfect fit for her son. Was it her fault?

Keeping an Eye on Things

Pinligheten begynte å krype opp på Madeline. Det virket ikke som om noen annen mor hadde nesten like mye trøbbel i barnevaktavdelingen. Hennes mors venner hadde alle nydelige langsiktige barnepiker som utviklet fantastiske forhold til barna sine. Hun følte seg ute av sted at ingen passet perfekt for sønnen hennes. Var det hennes feil?

So Far, So Good

Benjamin was being a pretty good kid for the most part. Madeline saw no difference in how he acted around her or Brooklyn. For a second, she almost let herself believe that it was the previous sitters who just couldn’t click with her son. She was happy they had finally settled on someone who had a good relationship with her son.

The Truth is Coming

It didn’t take long for things to start to change. Due to not having found anything on the footage, Madeline took a break from monitoring the two and decided to give them some privacy. After a month, though, Madeline noticed a real shift in the dynamic between Benjamin and Brooklyn, and it was starting to give her deja vu.

Old Behaviors Coming Back

One day, when Madeline returned from work, Brooklyn had left in a rush, and things felt a bit strange in the house. Normally, the babysitter was cheerful and talkative. On this day, she barely uttered a word to Madeline, nearly racing out of the house and barely making eye contact. This was suspicious to her. Maybe she should take a look at the cameras…

Temptation Rising

Madeline tried to talk herself out of it at first. Perhaps the girl simply had some personal issues she was dealing with, no biggie. But the behavior was feeling a little too familiar to her, and she instinctually knew it had something to do with Benjamin. Even though Brooklyn had seemed huffy, Benjamin betrayed no off-putting energy. He was happy all the way up until bedtime.

Doing Some Research

Patiently, Madeline waited until her son was fast asleep before reviewing the camera footage from the day. She didn’t want him to see what she was doing and suddenly be too self-conscious of his every move before she got to the bottom of what was really going on when she wasn’t there.

On the DL

Benjamin had a notoriously big mouth, and as kids are known for, he couldn’t keep a secret to save his life. Madeline worried if he knew about the cameras that he would tell Brooklyn and she’d quit out of discomfort. This wouldn’t do. There was no way Madeline could find childcare quick enough to replace her. Brooklyn had to work out.

What Were They Up To?

Finally, when everything in the house was settled and quiet, Madeline reviewed the footage. Nothing seemed off during the morning, and in fact, it looked like Brooklyn and Benjamin were doing fine pretty much all day. It wasn’t until the late afternoon that she noticed something really alarming.

Filling in the Blanks

The equipment Madeline bought did not record voices in her house, so she had to do some guesswork to figure out the conversations Benjamin and Brooklyn were having. At the time, it seemed like they were in the middle of a pretty heated discussion. Brooklyn was moving her arms wildly, and she could see Benjamin’s face tense up into a scream. He stormed off to his room and slammed it shut, leaving her perplexed in the living room.

Things Were Getting Weird

After an hour had passed, Brooklyn rose from where she sat on the living room couch and walked to Benjamin’s room, swinging the door open. She couldn’t really see the faces of either of them, but the discussion they were having still did not look friendly by any means.

Figuring It Out

There was not much she could discern, but the two had seemed to go back and forth for a few minutes. Though Brooklyn seemed pretty upset, Madeline appreciated how she kept her composure for the most part. She could tell that Brooklyn had a long career ahead of her in the education department.

Missing in Action

However, things took a strange turn of events. Benjamin didn’t seem to be offering too much of a reaction, and at that point, Brooklyn turned to leave the room, and to Madeline’s surprise, the house as well. Where had she gone? Madeline continued to watch the footage and was shocked to see it was an hour before Brooklyn had returned. And Benjamin had taken full reign of the house in the meantime.

A Boy of Mischief

Benjamin took his time to get into everything he couldn’t when there wasn’t somebody around to stop him. He dug through the candy drawer and had his fill of chocolate and other sweets. He found some matches in another drawer and tried his best to strike them, but failed. Madeline was horrified, Is this what he had done around the other sitters?

Finding Her Way Back

Brooklyn returned shortly, and there was visible tension between her and the young boy. She pretty much left him alone for the rest of the day until Madeline came home. She was appalled by what she had seen. Her son seemed to be an absolute nightmare for everyone else but her. Was this who he really was when she wasn’t home?

Coming Up with a Plan

Madeline couldn’t simply interrogate the two about what had happened this day. She had to be a little sneaky about it. Benjamin would never admit it if he did something wrong, he had to be caught. So, it was up to Madeline to figure out how to catch him in the act.

Technology to the Rescue!

Suddenly, it hit her. Madeline could adjust the cameras to a live feed from her cell phone, where she could watch intently to see when Benjamin would act up. Of course, she’d had to ignore her work duties for a bit, but this was way more important. She had to put a stop to this once and for all.

Taking a Leave of Absence

When Madeline told her boss that she’d need to take some personal time off, she was surprised at the amount of support she’d received. Madeline was a great employee, so her boss had no problem giving her a few days to figure out things at home. He barely asked any questions, which was a relief to her.

Any Day Now…

After about 3 days, Benjamin was back to his old tricks again. She noticed he same pattern from the other day. Brooklyn could not seem to get Benjamin to cooperate her, and after an argument, she stormed out of the house, leaving him to his own devices. Finally, this was Madeline’s shot to get to the bottom of this.

Surprise, Benjamin!

Madeline raced home, anxious to see what her son was doing. She hoped to get there before Brookyln came back so she wouldn’t have to explain how she knew Benjamin was alone. She snuck through the back entrance quietly, and crept around the corner to where her son was standing in the kitchen. Just as before, he was raiding the cabinets as he pleased, leaving a mess in his wake.

Explain Yourself

“Hi there, Benjamin,” Madeline said sternly, and the boy swung around, his mouth stuffed with chocolates. He immediately turned bright pink and tried to muffle some sort of excuse, but it was no use, He knew he had been caught red-handed. “What on Earth is going on right now?!”

Getting to the Truth

Benjamin had no way to escape. He finally had to tell his mother why all the previous babysitters had left so abruptly. She took him over to the living room and sat him down, waiting for him to explain what was going on. It took him a minute, but soon he was confessing everything that had happened in the past few months, and Madeline was shaken to her core.

An Evil Little Genius!

Benjamin apparently had gotten quite possessive over his babysitters, and it really upset him that they each had a life outside of him. He made it a point to get to know them well, asking innocent questions about their lives and suiting up with an arsenal of information about each sitter.

The Plan, Pt. 2

Over the course of a few weeks, Benjamin would ensure he was a perfect angel to each sitter, hoping that his calm and rational demeanor would ensure they stay forever. But, when one of them began a new relationship, got a new job, or even showed a little too much interest in their other friends, he would retaliate. And boy, it wasn’t pretty.

Doing Some Extra Research

Somehow, Benjamin would find these sitters on social media, where of course they would live their own independent lives full of drinking, partying, and all the normal things young people would do. Shockingly, he would use this information against him, threatening to tell his mom about their behavior outside of work, and even saying he’d lie and say they did the same stuff on the job.

Who Had He Become?

Madeline almost couldn’t believe this was her son. She had spent so long believing he was a perfect, sweet boy, when in reality he was sneakier than she could have ever imagined! She felt disappointed and hurt by Benjamin’s actions. This was certainly not how she raised him to behave, and she couldn’t help but wonder where he picked this behavior up from.

In Too Deep

For the most part, each of the babysitters refused to give into Bjenamin’s scheme, which is why they had left in a hurry one after the other. However, Brooklyn was simply too sweet. She was a pretty reserved girl with strict parents, and though she was in her twenties, Madeline knew the type of religious environment she’d grown up in from brief conversations with her.

Struggling to be an Adult

Brooklyn was in a sticky situation. If her family or parents ever had an inkling of what her life was really like, especially on social media, she’d be cast away from the family. So, not wanting to risk her status, she would give in to Benjamin after a while, waiting outside while he gleefully destroyed the house.

A Second Chance

This was not the type of person Madeline wanted her son to become. She was a single mother, and she had always taught him to respect other people and know their boundaries, Still, she knew that his behavior was partly a failure on her part, and she had to do anything she could to fix it. Just then, Brooklyn walked through the door, and shock flitted across her face. What was Madeline doing here?

I’m So Sorry

Just like Benjamin, Brooklyn fumbled for an explanation, but she was lost for words. She felt deeply ashamed that she’d allowed a child to blackmail her, and that she was so worried about her parents finding out about her life that she’d basically leave a child to his own devices. However, Madeline couldn’t bring herself to be mad at Brooklyn, She too had grown up similarly, and knew where she was coming from.

A Total Do-Over

Brooklyn, though upset with herself, begged Madeline for another chance with Nebjamin. Despite his actions, she really enjoyed her job, and she wanted a chance to see who the boy was really like outside of his manipulative behavior. Madeline took a minute, but in the end she agreed. Everyone deserves a chance to redeem themselves, especially those caught up in a less than desirable situation like this.

Things Were Changing

The next few weeks were completely different than what had transpired before, Madeline no longer felt the need to look at the cameras and had returned to work, feeling at ease that Benjamin was in Brooklyn’s hands. Benjamin’s behavior had flipped upon being caught, and he had turned into the ideal little boy. He was clean, kind, and had even learned how to have a healthy friendship with Brooklyn. Things were finally going Madeline’s way.

This story is a work of fiction created for entertainment. Characters and events are the products of the author’s imagination. The images shown are used for illustration only.