25 Babysitters Share The Most Awkward Encounters They’ve Had On The Job.

Babysitter can be such an awkward experience. Whether it's with the children or the parents, something about babysitting stories adds another level of cringeyness. Here are some of the most awkward encounters babysitters have had while on the job!

1/25. So I'm a female and I babysit two brothers (9 and 12). One day it was me, the brothers, and their dad in the car. The 12-year-old then randomly says "hey dad, don't sleep with this babysitter hahahaha".

Worst car ride ever.


2/25. I was once babysitting a 7 year old who was mad because I didn't allow him to go to his friend's house when his parents specifically said not to let him. He the proceeded to take a large knife and make small cuts on his arm and face and told me that he was going to tell his parents that I did it to him.

So I started secretly recording him in case the parents didn't believe me.

When his parents returned I had to explain the situation and of course they believed their precious son because he had (minor) cuts all over him and was crying hysterically. After being threatened, I showed them the video and they tried apologizing. At that point I was so fed up and annoyed and I left.

Needless to say, I never babysat for them again


3/25. Gave a four-year-old her bath. Halfway through, she pulls a small spoon out of her vagina.

She said she'd put it up there earlier. I asked if she had anything else inside her. She said no. Continued with bath.


4/25. I had to babysit a 16 year old. I'm 18. He wanted to have sex with me.


5/25. I was babysitting my boss' daughter, who was four years old and constipated.

The kiddo went to the bathroom, and remained there for like fifteen minutes, so I went in to find her after she did not come out. She was on the toilet, straining, of course. And I was about to leave her in privacy when she went and flailed her little arms and said the phrase that will live in my memory forever.

"You can't leave! You have to SQUISH me!"

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More hilariously awkward stories on the next page!

I had quite the WTF expression, I'm sure. So I went, "What?"

And she says, "When I can't poop, mommy and daddy always squish my tummy, so you have to squish me!" And she places one hand on her stomach, and one hand on her back, and demonstrates how to squish her.

So I accept her demands and gingerly put a bit of pressure on her stomach.

But, oh, no. "Harder! You have to squish me harder!"

So, I'm literally squishing the shit out of a small child for a few minutes until finally she breathes a sigh of relief and tells me she's done. She hops up off the toilet and there, in the bowl, is this tiny corn-kernal sized turd. I squished a baby for almost f*cking nothing.


6/25. I accidentally ate a stash of weed cookies when I was 12. In retrospect, it makes more sense now that they kept the cookies in the back of the cupboard above the refrigerator. I had to get up on the counter to reach them. I initially only planned on stealing one cookie, but I just couldn't help going back for more again and again. I was filling in for my cousin's usual gig, she was 16, she flipped when she showed up and found me all stoned.


7/25. In high school, I met a nudist family at the local nude beach. They asked me to babysit, figuring I'd be comfortable with their lifestyle. No problem, easy money. Two boys 7 and 9, we'll behaved. The weird thing was that as soon as the parents left for their night out, the kids would start putting on clothes. By the time, they got home we were usually bundled up watching scary movies on TV. The parents always seemed a little uncomfortable with that, like I'd been perverting their kids into putting on clothes.


8/25. Being six years old and barely being able to take care of myself, let alone an infant.

I came up pretty poor and my mom struggled to make ends meet. One day she had an interview and had to leave us (me and my brother who was 4) alone for 6 hours or so while she left to go to a job interview. Not to mention we were living out of a small motel room.

Anyway, I could handle my brother so that wasn't too bad but about 30 minutes later this junkie lady, who lived next door to us, knocked on the door calling for help.

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Since I knew her and saw she was in trouble I opened up the door. She then convinced me to babysit her 3 month old infant while she did god knows what and sh*t, I was six, what was I going to say, no.

The worst part was her leaving me nothing but some half-eaten food to feed the kid for the day. Hours later, my mom returned home and cursed me out for opening the door and taking the baby, though she knew that I was only trying to be nice.

The junky lady returned late that night and my mom went crazy on her. I never found out what happened to them, being that my mom got the job and we moved to an apartment soon after, but I hope that child ended up okay. I still think about it to this day.


9/25. New Year's eve. Parents come home midway through the evening to drop off one of their super drunk friends. He went to sleep in the three year old's bed and the kid kept going up to check on him like a little nurse. One of the kids reached for a glass of what I thought was water on the coffee table but I quick gave it a sniff and it was vodka that the parents left out when they went to the bars. Parents were so drunk they each tipped me a ton of money and told me not to tell the other party.

I made $90 that night which was amazing money in 1993.


10/25. Kid kept playing with his junk when I'd changing him and sing-song "playing with my pee pee.".


11/25. I'm a daycare provider. The weirdest thing that I have ever seen is one day I went in to work to find all the kids watching a scene from Futurama on loop. The dad looped the hypnotoad to see if it would work, and it did for about 20 minutes.


12/25. Was watching two boys, maybe 12 and 11. Well their parents liked to party quite a lot (one of the reasons they would pay me to watch their kids). One night they go out, order pizza for dinner and the delivery driver forgets the the soda. So the younger child says there is orange juice in the fridge, I grab the pitcher not thinking anything of it. Pour them each a glass, they drink and eat without saying word. Through the course of the night they keep pouring themselves cup full's of OJ. They start acting strange, stumbling, talking odd, etc. Call the parents and ask if I should do anything, then tell the parents everything they ate/drank.

Their dad ends up telling me the OJ was just a giant screwdriver that his wife and him were going to split when they got home. Luckily I didn't take too much heat for it because he said he should have warned me.


13/25. I babysat a 4 year old once, I was 20 at the time. In the basement lived a teenage brother to the 4 year old, a kid I wasn't told about until I walked in and the mom said "by the way my 17 year old is in the basement" as she ran out the door.

The little one went to sleep, the teen came up and asked me if I had any weed.


More cringe-y stories on the next page!

14/25. I haven't babysat in awhile but when I was a teenager I watched two kids up the street. The mother was single and had another single friend with two kids so I usually watched them all. I knew they went out to party- which was fine because they'd come home drunk and pay me more than I expected. What I didn't know is how much they partied. One evening I went upstairs to get money for pizza. I found both moms in the bathroom snorting coke.

The worst thing was when they offered me some despite the fact that A) I was about to spend the night watching their young children and B) I was only 14 or 15 at the time.


15/25. I babysat a little boy who had severe emotional problems. One time he ran away while I was upstairs playing with his sister. He ran away to the park down the block, climbed a tree and refused to come down because "no one loved him". I was young and didn't think about calling the police or anything. I just sat at the bottom of the tree and literally talked him down. I convinced him that I loved him and wanted him to come home. His siblings also helped me by saying they loved him also. It was so scary.


16/25. I was babysitting an eight year old who got pissed because I wouldn't let her eat a shit ton of candy at midnight when she was supposed to be in bed... so she sat on the kitchen floor and urinated.

I made her clean it up.


17/25. "I'm gonna cut you" - from a 3yo girl because I told her it was time to get ready for bed.


18/25. When I was 13 I got a job babysitting for my neighbours. They had two little girls that were just the easiest kids to look after. The mom and dad were super nice people. Dad was a nurse that worked mainly nights and mom worked from home and would ask me over Friday nights so she could go out and have some down time. I quickly found out though that she was seeing other men.

The first night I went over there the mom informed me she would be home no later than midnight. Well 4am rolled around and I'm woken up by noise out on the porch and see her hastily kissing another man and shooing him off. She apologizes for being late, pays me (was $5 short) and I go home to my mom whose pissed that she kept me so late. The same thing happened two more times. She'd promise to be home at midnight and come home at 3 or 4 in the morning. Every time with a different guy. And every time would stiff me a little of what I earned. My mom put a stop to it and called her out on cheating on her husband. They ended up getting divorced not long after that.



19/25. I babysat two girls maybe 8 and 6. Their mom said she was planning on being home around supper time. Well, supper time comes and goes and mom doesn't show. A few more hours and I receive a drunk phone call from mom. I asked her when she expected to be home and she said she didn't know. She asked to talk to her oldest and I put the little girl on the phone. Kid gets upset and runs out into the night. I panic but manage to find her. She was hiding in the yard, didn't get too far.

Anyway, long story short, it's now the next day and I call a friend of mine to take over since I was exhausted. Mom shows up 3 days later and gives my friend $20 to give to me. Im furious and vow to never sit for anyone again. A few weeks go by an her boyfriend shows up and apologizes for her actions and hands me $150.


20/25. Babysat my two year old brother and he ate his own sh*t.


23/25. Mom and dad came home drunk, and fighting. The dad went out to walk the dog, and the mom locked the door with me inside. She kept saying "shh-shh," while the dad screamed from the outside.

She started saying things like, "He wants to kill himself instead of be with me - who says that?"

I reached for the lock to get out, and she pulled my hand back saying, "No, leave him for a while."

I waited as long as I could, then busted out of there.


24/25. I babysat regularly as a teen. One night it was business as usual. I had just laid the kids down for bed until I hear crying in the bathroom. Go in and the little one had a poop string hanging out of his bottom. I didn't want to pull it in case it was wrapped around something so I'm trying to keep this kid calm and call his parents. They don't answer. I call over and over with this kid freaking out. I call my mom who calmed me down, took their number, and then chain called them until she got a hold of them. They "rushed" home and took him to the ER.

Definitely my weirdest night. The string came out fine, btw. Apparently the kid liked yarn.. a lot.


25/25. I have rather hairy legs and I was wearing shorts. This four year old boy just gets on the floor and starts petting my legs like I'm a dog.


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