15 Most Awkward Moments Teachers Have Ever Experienced

4 min


Teachers are faced with awkward situations on a daily basis. Whether it’s a curious question from a kindergartener, a remark from a pubescent elementary student, an inappropriate action by a high schooler, or an embarrassing encounter with a parent outside of school, it’s almost impossible to avoid. Teachers always have to keep a straight face and find a diplomatic way to stop the moment from turning into something else. Here are some of the weirdest, funniest, and gag-worthy moments teachers have shared on Reddit, Twitter, and Facebook.

What’s the most awkward teacher moment you’ve ever had? Let us know in the comments!

1. “My pants split…”

2. “Get off my D!”

awkward face

“My classroom carpet had the alphabet border around the edges. One of my pre-school students, Demetrius, likes to sit on the letter D because it’s the first letter of his name. One day, Zaria sits on the letter D. Demetrius gets in her face and yells, ‘Zaria! Get off my D!’ I lost it.”

3. “Where’s the hole?”

Awkward face gif

“Child: Ms. Justgoodenough, do babies come out of the belly button?
Me: What? No! What are you talking about?
Child: The baby grows in the mom’s tummy, right?
Me: Well, yes, sort of.
Child: Then how does it come out? It has to come out somewhere. Where’s the hole?!

Me: Extremely awkward silence You know what? I don’t have any kids. But your mommy has had two kids, so I bet she knows a lot more about this than I do.”

4. “Can you do this?”

Embarrassed girl hiding behind hand

Had a “can you do this?” contest with a fifth grader.
“Can you do this?” I roll my tongue.
“Yup!” He does the same.
“Can you do this?” I flare my nostrils.
“Yup!” He does the same.
“Can you do this?” I cross my eyes.
“Actually, I had an operation when I was little so I would stop doing that.”

“Oh. That’s good. I, uh… goodbye.”

5. “It’s the law.”

Britney Spears awkward face

“My sophomore year of college I was involved in a volunteer program that sent me to a local high school two days a week. I basically just helped an 11th grade CORE teacher with computer lab stuff and ran errands, nothing spectacular, but it was an easy college credit. My last day of the term one of the male students presented me with a wrapped thank you gift. I thanked him profusely before opening the gift, which turned out to be a highlighted printout of our state’s consent laws.”

6. “I wrote a bad word on the board”

Embarrassed girl hiding behind hands

I wrote the word can’t on the board, but didn’t close the top of the A all the way, so it said cunt and I didn’t realize it. The whole class was laughing for a good ten minutes before I figured it out.”

7. “My boobs were out and in my hands.

Couple embarrassed face "Whoops" gif

I had just had a baby and frequently had to use a breast pump. I locked my door, but it didn’t latch properly. My boobs were out and in my hands; the pump was working; my milk was flowing. Suddenly a fifth-grade boy bursts into the room. I can’t drop my pump without spilling milk all over the floor, so I stand up and run across the room screaming “Get out!” in a panic. The boy goes back to his other classroom. I’m absolutely mortified. Once I calm down I call his classroom and ask his teacher if he said anything. She said, “yes. He said you were talking on your cell phone.”

8. “Shopping cart full of alcohol.”

Reese Whisterpoon "I want to die right now"

“Ran into one of my students’ parents in the grocery store (who is a very active member of the local church), with a shopping cart FULL of wine. There was a sale on my favorite wine and I was getting a bunch to give as gifts, and to stock up for myself of course. The next parent-teacher meeting was pretty awkward.”

9. “I’m totes hung.”

"Awkward alert" gif

“You know how kids these days shorten words like “awk” for awkward, “totes” for totally, etc? It was lunch time and I was in a good mood and felt like being that “teacher that tries to be cool but isn’t” to get a laugh out of the students as it was a Friday and we weren’t terribly busy. I tried to shorten a word. “Yeah, I’m totes hung”. Meant it to mean I’m totally hungry. I couldn’t recover and after about 3-5 seconds everyone clicked into what I said.”

10. “What can I do to get an A?”

Justin Timberlake "Awkward face'

“I had a 15-year old student send me a photo of herself in lingerie with the line, “What can I do to get an A?”

11. “It’s going to be a while.”

Maria Carey awkward face gif

“I was with a student, waiting late after a rehearsal. The kid called home: ‘Hey, can you tell mom to pick me up? Oh, she’s in the shower what about dad? He’s in the shower too .?’ Then he turned to me and said, ‘It’s going to be a while, Mr. M.’”

12. When you show up to school and one of your students is wearing the same outfit as you.

Tweet of teacher and student wearing same dress. Caption " That awkward moment when you turn up to work wearing the same outfit as your sixth form student

13. “It went back in.”

Afraid face gif

“Student: Can I go to the bathroom?
Teacher: In a little bit.
Student: (raises hand)
Teacher: Yes, I’ll write you a hall pass to go to the bathroom now.
Student: Nevermind, it went back in.
(awkward silence)

Teacher: OK…”

14. “Ran into one of my students in the store.”

Actresses awkward faces

“Ran into one of my students in the store. The only items in my cart were tampons, duct tape, and motor oil. He looked at my cart and his eyes got large. Not sure what he was imagining I was going to do, but we both acted like it never happened the next day in school.”

15. “I accidentally told my year 3 class that Santa wasn’t real.”

Teacher awkward face

Playing a game of guess who with the kids.
Child: “Am I a man”
Me: “Yes”
Child: “Am I famous”
Me: “Yes”
Child: “Am I real”
Me: “No. No, I’m not real.”
5 minutes worth of guessing later after which no child guesses correctly
Me: “C’mon guys! I was Santa Claus!”
10 seconds silence
Random child: “But…does that mean Santa isn’t real?”
30 faces in the room staring straight at me with a few on the verge of tears. I had that filthy sinking feeling for a good 10 seconds before I passed it off as a mistake I had made. But a few cluey kids had caught on after I stupidly emphasized the “No”. Oh God, I still cringe.

What’s the most awkward teacher moment you’ve ever had? Let us know in the comments!

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