These Principals Have Us Rolling With Unbelievable Never-Have-I-Ever Moments

When you’re a principal, no two days are the same.

There’s never a dull moment in the life of a principal. Just when you think it’s been unusually quiet or without incident for a few days, you’ll get something totally different or unimaginable to deal with, like the moments described below.

Thanks to all the principals who contributed stories for this piece—yes, we kept our word, and you are all remaining anonymous! We know the life of a principal is not easy, and we appreciate having some insight (and a few laughs) about what goes on during your day. Check out these unbelievable principal life stories about parents, staff, and students. 

Never Have I Ever: The Parents 

You are under arrest. 

Never have I ever had a parent leave me a voicemail threatening to have me arrested. They were upset I wasn’t answering my phone at 5:30 PM the day before Thanksgiving break. Give me a break!

Did someone call for a restraining order? 

Never have I ever had a parent buy a teacher rose-shaped panties for Valentine’s Day. When served with a restraining order, he claimed that’s what his daughter wanted to buy for her first grade teacher.

No fighting on school grounds. 

Never have I ever broken up a fight between two moms in an alley beside the school while a crowd watched. One of them was pregnant.

Stop with the poop pics already!


Never have I ever had to ask a parent to stop texting pictures of her second grade daughter’s poop-stained undies to classroom teachers. She claimed the little girl needed assistance wiping, and she wanted us to SEE why.

There’s a peep show happening in the office. 

Never have I ever had a parent dressed so inappropriately that when she was signing her child out, she didn’t even notice her exposed areolas were resting on the secretary’s desk.

What am I even paying for? 

Never have I ever had a parent tell his kids that he pays too much in tuition for them to be acting up at school. (It was a public school. His ex had him paying her for monthly tuition.)

Never Have I Ever: The Staff

Keep your hands to yourself. 

Never have I ever had to send a substitute home for pinching the nipple of a little boy to make him behave in class. 

I’ll be right back. 

Never have I ever had a teacher work all day and leave her husband waiting in the car for her—every day for an entire school year.

It’s time to peace out. 

Never have I ever had a teacher come in for summer professional development, go to the restroom during the first hour, then leave and never come back. 

It’s a different kind of juggling act. 

Never have I ever had a teacher have affairs with four of his coworkers, including his co-teacher.

Let’s have a chat about the dress code.  

Never have I ever had a first year teacher dress so unprofessionally that I had to take her to the mall MYSELF and help her pick out skirts and dresses that were an appropriate length. This was after sending her home to change three times in two weeks.

Hello, can I help you? 

Never have I ever fired a teacher and then made an appointment to look for a new house—only for that teacher to be the realtor. Awkward.

Please keep your shoes on at all times. 

Never have I ever had a teacher put his foot on a student’s desk and cut his toenails while teaching.

Time for a drink. 

Never have I ever had a teacher preview vocabulary words from “Little Red Riding Hood” to a second grade guided reading group and explain that a “night cap” is a drink you have after dinner. Really? It’s just granny’s sleep hat.

Is that a threat? 

Never have I ever had a teacher believe her room was bugged and that there were cameras in the smoke detectors. This teacher is the same one who called the vice chair of the board and threatened to cut my balls off.

Never Have I Ever: The Students

Can someone bring me some toilet paper? 

Never have I ever had an eighth grade student who took really long bathroom breaks. One day he used his cell phone to call the front office while in the bathroom. He wanted to let our secretary know that he was out of toilet paper!

Stop bullying me.

Never have I ever had a kindergartener tell his mother that the child who sat next to them was bullying them and cut a patch out of his hair. But when I reviewed the video from the classroom, he was cutting his own hair and blaming his classmate.

Fake it until you make it. 

Never have I ever had a middle schooler drive to school and park her car in between the staff cars.

It’s a lunchtime happy hour! 

Never have I ever had a student raise his Apple-Ahhh-Rita in the air at lunch time. He said, “I think my mom made a mistake when she packed my lunch. This is not apple juice, right?”

It wasn’t me. 

Never have I ever had a third grader remove the top off the toilet tank to urinate. He would STAND on the seat and go inside so that every time you flushed the toilet, pee circulated the fresh tank. Mom insisted he didn’t do it—she said his urine stream was too “jerky” for that to happen.

Keep it on the DL. 

Never have I ever had students use school currency to create a drug ring, selling Benadryl. They were selling them as “pinkies” to other students during school hours. They were disguising them as mints by putting them in Icebreaker containers.

This is not in the job description. 

Never have I ever been asked to help an elementary school student wipe his butt after a number two.

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