13 Crazy Awkward Things Kids Have Asked Their Babysitters

Babysitters love their jobs because kids are naturally adorable, at least thats what we hope; right mommies? But children can be downright clever and frighteningly witty at times. It’s also one of the reasons why most of us can really get scared about having conversations with them (especially if the conversation is about sex).

And sometimes, their questions can just sweep the best of us off our feet, wether we are their parents or not. Check out these hilarious, awkward and crazy questions that kids have asked their babysitters:

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13 Feisty Little Lover

One time, my neighbour asked me to look after his 7-year-old son for just a whole afternoon. The boy, Kenny, was acting kind of weird around me like he was being impressive and all. Then, he went to his parent’s room and after a few minutes he got out wearing his dad’s coat and a messed up tie.

It was cute just before he asked me in a teasing voice, “So... what does a guy like me have to do to get a gal like you?” No idea where that kid got that line. It was disturbing for me, obviously, and I never dared to babysit him again. Till this day his parents don’t know why I won’t work for them

- Jamie S.

12 Obsessive Kid

There’s this kid from the neighbourhood which I babysat for when I was a teenager. Their home was just across the street so going over wasn’t a problem. It didn’t take long before I got to know her. She was kind of clingy and overly possessive of me, which to me was fairly tolerable.

Then, one time she took it too far. I was babysitting her while her parents were on a date night (my first night with her) and at around 11 pm, she asked me, “Can I keep you forever in my closet?” It was so weird! I know in my head that it wasn’t meant to sound crazy, but I totally over reacted. I quit right there and then.

But ever since that day whenever I go out, I’d see her from their window, looking at me. Just staring and smiling.

- Seth R

11 Making Babies with Mommy

I won't forget the day when my 3 year-old nephew asked me where babies from. I said, “Well, when you grow up, you’ll choose someone you love and then you two will magically know how to make babies!” Then he said, “Well, I love mommy so I’ll choose her! And then we’ll make hundreds of babies together!”

It was the most awkward thing I’ve ever heard. And to my embarrassment, his mother was standing right behind me.

- Tiffany Q

10 Victoria’s Secrets

Last summer, I babysat for my neighbour’s little girl Brittany. One time, she asked if teachers can sometimes tell us the wrong things. I asked her why and she said, “My teacher told us that boys wear briefs. So, why was daddy wearing mommy’s panties the other night?”

Oh my God, I’ve never been this embarrassed before. I said nothing. What did you expect me to say to a 5-year-old? And being the annoying kid that she was, she didn’t stop asking me that question till her parents finally came home.

- Rosie D

9 “Bad” Nanny

One time, I had to look after my neighbour’s 4-year-old son. She said they had to fire his nanny, but didn’t say why. That evening, I gave him warm milk but he threw it at me and cried. I asked him what was wrong and then he said, “Why didn’t you put vodka in it?”

Startled, I asked him, “Why would I?” and he said, “Because nanny used to!” Turns out, the last nanny was a drunk who had got the baby hooked on to alcohol and his mother wanted the next nanny to get rid of his addiction.

-Jennifer M

8 “Tonight, There Shall be Blood”

My friend asked me to look after his 4 year old daughter Stacy one time. I just had to watch after her while her grandma did the house work. That afternoon, we watched the movie “Tangled”, which is the one about Rapunzel. Stacy asked me why Rapunzel had to kill her mom. I told her it’s because the evil mom locked Rapunzel up the tower.

Then, she frowned and said, “My grandma never lets me out of the house. Can we kill her? I have the perfect plan!” She appeared dead serious when she said this.

- Jake J

7 Now, Kiss

One time, my sister and I babysat for our neighbour’s 5-year-old twins. One was a boy and the other a girl. Suddenly, they asked us this strange question, “Do you guys kiss each other?” We laughed and I said, “I can’t be her girlfriend because she and I are siblings, like you two.” “But we do. See?” they said as they smacked each other right on the lips.

“Now, you two do it!” they demanded. Most. Awkward. Day. Ever.

- Theron S

6 The Elephant in the Room

My nephew once asked me if elephants could survive elsewhere besides the jungle. “The zoo, I guess,” I replied. “What about inside a house?” he asked. I asked him why he was asking such questions and to my surprise he said, “I’m worried about mommy.”

Confused, I said, “What’s an elephant living in a house have to do with your mom?” He replied, “I heard daddy said to mommy that she’s starting to look like an elephant.”

- Taylor H

5 When You Thought You Knew Everything About Death

The day our grandpa died, I had to look after my 6-year-old cousin when everyone else was busy with all the visitors who came. He was asking me about how grandpops died and so I explained it in a way that he could understand. Then we found ourselves talking about what happens to people when they die.

I told him, “Well, we leave our bodies, become souls and go to heaven.” “What about grandpops’ body?” he asked. “The, uh, worms would eat it. But that’s okay because that’s what worms do. They eat dead bodies,” I said as I try my best to explain. Then, he said, “Well, who’s going to eat the worms when they die?”

I just don’t understand why children these days are so smart. They make the rest of us look like idiots, especially when you can't answer their questions.

- Jenille F. C.

4 Bird Man!

One time, I watched over my neighbour’s 3-year-old for her while she was away for work. The boy asked me what I do and I said I just graduated from middle school. I told him that I’ll be a pilot someday. “Can I be anything I want to be, too?” he asked and I said, “Yes. Anything you want to be!”

I never thought he would contemplate what I said so much, but the next day, when I came over there was no one at home. The guy next door said he saw the whole thing in the morning, “They’ve gone to the hospital just now. The kid just went nuts! He was shouting ‘I can be a bird! I can be anything!’ before he jumped right off the roof. Broke his arm but he’ll be fine.”

- Christina A

3 Serial....oops! Cereal Killer

One morning, I was preparing some breakfast for my 4-year-old niece. She just woke up and spent a few minutes on the couch while the news was on. I got her some milk and a bowl of cereal. When she saw it, she suddenly screamed.

I asked her what’s the matter and she said, “I don’t wanna go to jail, Aunt Martha!” “What are you talking about, young lady?” I asked. “The man on the TV! He was uh, a CEREAL KILLER and they said they were locking him up! I don’t want to eat cereals anymore!”

- Martha S

2 Private Furry

Once I babysat for my best friend’s 5-year-old son, Johnny. He was animated and a cool kid. We also had something in common: we both love dogs. They had a Shitzu named Berny which is why I enjoyed my time with them even more. Once, I was trying out some tricks on Berny and told him to play dead.

Berny dropped and lay on his side with legs wide open. Johnny pointed down towards Berny’s private part and asked me, “Uncle Lou, what’s that funny thing on Berny’s stomach?” “That a, uhm, his penis, sonny. Just like the ones we use when we pee.” Out of the blue he said, “Mine’s not furry at all. Is yours furry? Can I see?”

And he didn’t drop the subject for the entire freaking day.

- Louis R

1 The Origin of Everything

Once I was playing and looking after my cousin who’s a 5-year-old boy. I told him that everything in the world has its own origin. I told him that humans had monkeys as ancestors, and lizards had dinosaurs. Then he said, “Could it be that mommy’s boobies came from balloons? They sure look like it, only sad ones.”

Oh my God, I’ve never laughed that hard in my entire life.

- Prakaash S

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