A freshman boy, fifteen, landed in my remedial class mid-semester. He’d been a problem in his previous class, and he’d only shown up there a few weeks before because he’d transferred from another school. Minor red flag. But in my room, he was a great student.
His real issue was that he was too smart for the material and bored out of his mind, which usually leads to trouble. And his home life was basically in the gutter. I won’t get into the details, but it was bad. I brought it up with the school counselor.
She did some digging, confirmed a lot of it, but with a whole student body to handle, there wasn’t much she could do. He wasn’t, in her words, in immediate danger. I talked to his former teacher, the one whose class he’d left. She thought he had issues with female authority figures, possibly stemming from something at home—maybe his mother or older sister.
She could never get anything out of him. Things were going fairly smoothly until he showed up one Friday during lunch and said he’d come to say goodbye. That’s a red flag. I got him talking.
He said he’d hit a breaking point at home and was going to run away. He had a girlfriend who might let him crash for a few nights while he figured things out, but that wouldn’t last, and his mother would find him there quickly. From there, his plan was to be homeless or attempt suicide. He rationalized that either would end the bullshit or at least get him a real bed and a few meals in a hospital.
I went through a mental checklist. I asked him to reconsider, tried a few angles, and eventually talked him into trying to reconcile with his mother, for the sake of his younger brother. I asked if having a few days away from home might help. Reluctantly, he agreed.
So after school, I took him home with me. He slept on my couch, did chores around the house and the yard, and was respectful to me, my wife, and my own kid. We got him to call home on Friday. It ended in a shouting match over the phone.
Again on Sunday morning—less shouting, but still tense. I told him he’d need to go home that night, try to talk to his mom face-to-face. I gave him some de-escalation tips and drove him there. He was at school Monday and seemed fine, though still agitated.
Then his mom started calling me repeatedly, accusing me of molesting her son and grooming him for molestation, shouting and ranting. I told her that if she felt that strongly, she could go to the authorities. But I had weeks of documentation about his condition, plus his own testimony. I had the best interests of one of my students at heart.
If she cared about his health and well-being, she might want to examine her own relationship with her son. I subbed for a high school Spanish class one day. A female upperclassman showed up during my planning hour looking for the regular Spanish teacher. After learning the teacher was absent, she stuck around and started small talk, claiming she was a teacher’s aide in gym and wasn’t needed that day.
Based on instinct alone, she seemed too friendly for someone who’d never met me. Something felt off from the start. I propped my classroom door open and didn’t give her much feedback as I prepped, but she kept talking, and it kept getting more personal. Without any prompting, she explained how she’d moved out of her parents’ house.
She looked sixteen or seventeen and now lived with three college-aged guys while working as a waitress at what sounded like a strip club. That’s not the type of thing you open up to a random substitute teacher five minutes after meeting. Then she moved on to men’s fetishes, and how some of the people she served had a thing for pregnant women. It seemed like she was fishing to see if I’d open up about my own interests.
That wasn’t going to happen. I try to be a good listener for students under most circumstances, but this one set off alarms. I stood up, asked where the drinking fountain was—I already knew—used it as an excuse, and left the room. I didn’t come back until my planning hour was over.
I left that day wondering if I was just paranoid, or whether a girl with that kind of story should’ve been reported to the front office, or whether it was a home-life issue and therefore out of the school’s control. Either way, it probably tops the awkward teaching moments I’ve had so far. Looking back, I wish I’d reported her. It’s easy to see the answer in hindsight.
As a young teacher just visiting that school for the day, it became on-the-job training: when in doubt, tell someone. I was a long-term substitute in a rural high school, fresh out of college, teaching history. This girl, probably sixteen, texted the entire class without stopping, even after I warned her. I finally confiscated the phone.
The rule was that only a parent or guardian could get it back, at the end of the day, because the school was still dealing with the fallout of a major sexting scandal. During lunch, I was setting up a lesson for the next class when the girl came back in and asked for her phone. I told her it was already turned into the office. She got annoyed and asked me to call down and retrieve it.
I said I couldn’t. She started bawling, saying her parents were out of town until Saturday, and since it was a three-day weekend, she couldn’t get it back until Tuesday afternoon. I told her I was sorry, but rules were rules. She switched gears immediately.
She started asking about my wife and son. I told her it wasn’t the time or place. With zero humor in her voice, she looked me in the eye and said if I called down to get her phone back, she would give me a blowjob. Without skipping a beat, I reopened the door she’d closed and waved for the teacher across the hall to come in.
When the teacher entered, the student stormed out. I explained what happened and immediately reported it to the principal, who called the girl in. During the conversation with the principal and the school counselor, she admitted she had offered to blow me, then added, “You must be the ref. ” The girl was sent back to class, and the principal called the superintendent.
It snowballed all the way to a meeting the next week—student, parents, school administrators, their lawyer. The parents were irate and accused me of molesting their daughter. Luckily, there was enough evidence to prove nothing happened. Once the parents realized their daughter had caused this massive embarrassment, they pulled her out and homeschooled her.
I was only there for another week, but I decided to stop subbing after that. I watched a porno with my English teacher months before she retired. We were quite uncomfortable. In my senior year English class, we had to present a multimedia project on a Shakespeare play.
I’m not great with Shakespeare, but it was the one with “double, double toil and trouble. ” The group acted out that scene, recorded it to VHS, explained the context, and turned in the tape. Two months later, the tape was returned, and one of the kids put it in the VCR for the class to watch. Act 1, Scene 1 went fine.
Act 1, Scene 2 had been spliced to include a blonde woman with massive fake breasts going to town with a dildo. Everyone sat stunned. The kid who’d played the tape stammered, “I didn’t—we didn’t do that. That’s not our tape.
” The ancient English teacher screamed from across the room, “Turn it off. Just turn it off. ”
She was old and about to retire anyway, but that event was the nail in the coffin. There had been rumors she might stay part-time or teach another year, but all of that was quashed.
By the next class period, everyone had heard what happened, and those of us who’d seen it were hounded for details. Rumors flew about who doctored the tape, but the truth was never revealed before graduation. It still comes up at class reunions. Nobody knows what really happened.
When I was fifteen, our old principal retired, and a new headmistress started. She wanted to introduce herself at a big assembly in the main hall. She was in her mid-to-late forties, a blonde white woman with short cropped hair. She had a PowerPoint projected, showing slides of her family and telling us her whole life story.
She had two eleven- or twelve-year-old mixed-race daughters who had just started as freshmen at the school. The next slide was a picture of her husband—a good-looking, huge, muscular Black guy. As soon as his picture came up, a kid named Dylan yelled across the whole assembly hall, “She likes big Black dick. ”
There was a split second of absolute silence.
Even the teachers didn’t know how to react. She froze on stage. It was so awkward to watch. Then people started losing it laughing, and you could see teachers pushing through the crowd, trying to find the kid.
She recovered quickly and moved to the next slide, pretending she hadn’t heard a thing. I’m not a teacher, but this happened to me in high school. I had an English teacher I found very attractive. She was sweet, and I’ll never forget her smile—just seeing it made me happy.
But she also had huge breasts, and I was a horny high school guy. I couldn’t help having sexual fantasies play out in my head during class, especially when I was bored. They ranged from past experiences, to porn, to any hot girl I wanted to be with. One day, I was daydreaming about her, and it was vivid.
I mean, my brain had a talent for creating vivid mental porn. It was horrible, though I was secretly proud of my visualization skills. Obviously, doing that can cause certain things to arise. Embarrassed, I looked down at my throbbing shame, hoping no one would notice.
As soon as I looked up, something in my head told me to glance across the room. My teacher was trying to look under the table to see what I was looking at. She was convinced I had some device out and proceeded to interrogate me in front of the class. “Jay, what do you have in your hands?
”
It was my throbbing shame, which I was clutching hard, hoping to make it go away. I looked up and said, “It’s not what you think it is. ”
Then she made my greatest fear come true. “Get up,” she said, and my shame decided to get even harder.
My face burned. I was embarrassed and turned on at the same time, trying to figure out what to do. All my high school brain could produce was, “Miss, I really don’t want to do that. ”
She retorted, “Jay, stand up, move your hands, and hand over that device, or I’ll send you to the office.
”
The shame kept throbbing. The class kept staring. She marched toward my desk with annoyance written all over her face. My heartbeat quickened.
She stopped right over me. “Move your hands,” she said, and pointed. I didn’t know what else to do. I closed my eyes, turned away, and moved my hands.
She let out a gasp. My eyes snapped open. “Oh? What—what do you mean, ‘oh’?
” I tried to look at her, but her eyes were avoiding mine, and a pool of red was washing over her face. She then addressed the rest of the class, who had been watching but had no idea what was going on. I returned to the assignment, and she trailed off as she walked away. That was the moment my teacher saw my erection.
She never looked at me again for the rest of the year. I was part of the school support staff in my early twenties, grabbing lunch in the cafeteria when a young woman behind me said, “Looks like you’re having a bad day. ” I replied something like, “I’ve had better. ” She stepped toward me, opened her arms, and said, “Looks like you could use a hug.
” I talked her out of it, saying I wasn’t really into hugging high school students, and escaped with a pat on the back. I almost forgot about it until Valentine’s Day a few weeks later. I got a card from her. It wasn’t sexual or anything, but given the possible situation brewing, I passed it on to the principal.
I figured maybe she was just trying to be nice to the grumpy guy, but I didn’t want to end up in a situation where I walked into a room with a student planning something compromising. I hoped she didn’t get in trouble. The high school was relatively mellow, but the middle school was a different story—pubescent girls fanning themselves and waving at me, the computer guy, as I passed, and boys acting macho and dying to impress them. I handled the boys by giving them Hello Kitty desktop themes in the computer lab.
The girls I just avoided. We had an English teacher who student-taught at the high school before getting hired at our middle school. She was one of those short, cute girls who looked younger than she was, so naturally, the high school guys walked all over her. My older brother and his friends noticed several times that her panties would peek above whatever pants she was wearing.
One of my brother’s friends, a known creep, managed to snap a picture of one such incident before she finished her time at the high school. By the time she was hired as a middle school teacher, I was in her class. The photo had circulated all around the high school and was now getting into the hands of the guys in my grade. One creepy kid in my class had a printed copy taped to the inside of his notebook cover.
One day, the cover got too tattered and fell off in class. The teacher noticed the picture. She was betrayed and quietly asked the kid to stay after class. He spilled everything, so he wouldn’t be pinned as the creep who took it.
She became so embarrassed she started looking for a new job. She left two years later. I still loved her class, though—I got an A, and she said I had a knack for storytelling. I taught a kid in seventh grade who was also my friend, the librarian’s student aide in eighth grade.
He had horrible acne and was often bullied for it. For his birthday, we decided to put together a small shaving kit for him—cologne, soaps, a razor, and other items. We ordered a pizza, decorated the library, and had a small party. When he opened his gift, he started to cry.
At first, we thought it was happiness, but it quickly escalated into sobs. We thought we’d offended him and began to apologize. Through his tears, we finally made out, “I thought it would make him stop. ”
We looked at each other and gently asked what he meant.
Slowly, the story emerged. His father had been sexually abusing him since he was five. He thought if he made himself as gross as possible, his dad would stop. By law, we had to call Child Protective Services.
We explained that to him. As I went to make the call, my friend tried to console him on his birthday. Then his mom showed up to pick him up early, arriving just after CPS. The caseworker let her into the room, and the first words she said were, “Couldn’t you just hold on for three more months?
” She had known what was happening and was getting her LPN so they could move out. She had never worked before this. That sad story has a happy ending. CPS, in conjunction with our school social worker, found them a shelter so they could stay together.
The father was convicted and sent to prison, where he was eventually stabbed to death. I should explain that the mom was regularly beaten and told she and her son would be killed if they tried to leave. I’m not excusing her behavior—just adding context. I’m not a teacher, but being the class clown often caused awkward moments.
In eleventh grade English, my friend and I sat in the last two seats in the last row against the wall. Our teacher was beautiful and the subject of many inappropriate conversations between us. One day after getting stoned at lunch, we got into it about her, too toasted to notice how loud we were until the whole class laughed and interrupted her lesson. Cool as the other side of the pillow, with the slickest smirk, she responded without missing a beat, “By the way, boys, I’ve heard everything you two have said about me all year.
” It was one of the scariest, hottest, most awesome things I’ve ever experienced. Another time in government class, we had to do a ten-slide group PowerPoint on a president of our choice. I chose JFK, and my partner was basically nonexistent. By presentation day, I had two empty slides and was short on facts.
I stumbled across his autopsy photos and used them as the last two slides, with one page mostly about conspiracy theories from that day in Dallas, and the last slide a recipe for Jell-O brains. I got a 90—minus ten for not completing the task, but plus ten for creativity—making it a perfect 100 for doing the whole project myself. I’m not a teacher and don’t plan to be one, but I have a great story. In tenth grade geometry, my teacher was absent and we had a substitute.
He was supposed to go over the directions left by the teacher—a brief math lesson followed by a movie. For some reason, he decided to scrap that and instead talk about sex to a bunch of tenth graders. He told us how he was a thirty-five-year-old virgin waiting to meet his love and marry her. As if that wasn’t bad enough, he was talking to fourteen-year-olds about this instead of teaching math.
He wasn’t the most appealing guy either—tall and skinny, round dorky glasses, bald head with a crown of hair. I zoned out, knowing this would get him fired. It did—he was fired immediately. The most awkward part is that I still see him almost every night when I cross the street after work.
My friend was in high school on a history trip with a history teacher and a young teaching assistant. She kept playing with her phone despite repeated warnings to put it away. Finally, the teacher said something like, “If I see that phone one more time, there’s no telling what I’ll do with it. ”
At the trip, they were visiting an old army fort being remodeled, with only portable toilets nearby.
My friend wanted to use her phone but was afraid of being caught, so she ducked into an unused port-a-potty. When she finished, she tried to put her phone in her purse. It slipped, and it fell into the toilet. Even though it hadn’t been used, she was too grossed out to fish it out with her hand.
She ran to find the assistant for help. It took a while, but she found her inside one of the buildings. As they were leaving, they saw, to their horror, the teacher leaving the port-a-potty and walking to the other side of another building. As my friend and the assistant approached the toilet, my friend kept repeating, “Please don’t let what I think she did be true.
” It was true. The teacher had taken a dump on her phone. They were both disgusted and found the teacher. The teacher didn’t believe them until they showed her the evidence.
Mortified, she removed the phone with a plastic bag and cleaned it off with tissues. My friend refused to believe it wasn’t deliberate after what the teacher had said on the bus. There was a conference with her mom, the principal, the teacher, the assistant, and my friend about it. When I taught high school summer school, the principal had a no-passes policy since the kids were only in school for about three hours with a long break in the middle.
We got back from the break, and a young man immediately asked to go to the bathroom. I reminded him of the policy. He started yelling about having an infection and needing to pee, then threatened to piss on my desk. He went so far as to unzip his pants—which I heard more than saw, because I had turned away to use the phone.
The rest of the class pretended to do silent reading. I called the principal to either escort the student to the bathroom or remove him from school for the day. When he heard that, the student started screaming about the principal wanting to see his dick and watch him pee. He got suspended for the rest of the day.
When he came back, I just acted like it never happened. I also worked in a juvenile detention center. There were a lot of rules and lingo I didn’t know, so kids unintentionally put me on the spot. One day, my boys’ detention class was writing poems.
This class changed every day based on who had been picked up the night before and who was waiting for trial—not like the constant groups that stayed for months. It made for interesting one-day lesson plans, but it also meant I never knew who I’d have. It was sad seeing the same kids come back after being released and getting in trouble again. Anyway, a new boy chose to write his poem about his grandmother.
It was a simple form poem, not intense at all, but suddenly he was sobbing and asked me for a “PTO. ” I had no idea what that meant. Hearing the “O,” I thought “officer,” and said, “Sure, yes, I’ll get someone. ” The students traveled with a guard, so I turned to him for help, thinking we were dealing with a meltdown.
He just shook his head and told the kid no. I later found out a PTO is a “personal timeout,” which the kid had been abusing all day to get away from the group and out of typical juvie situations. But to me, he seemed genuinely upset about his poem. He wrote me a note on the assignment, apologizing for crying, but saying he realized he might not get out to see his grandma again before she died.
I never asked the kids why they were there. I figured maybe he did something awful and knew he was headed to real prison after juvie. Awkward as it was then, I now joke with my regular high school students that I once made a kid in juvie cry.