Cart 0

15 Most Awkward Moments Teachers Have Ever Experienced

awkward teacher moments_feature image_Bored Teachers


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 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 teacher moments_Bored Teachers 1

“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 teacher moments_Bored Teachers 2 

"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?"

awkward teacher moments_Bored Teachers 3 

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."

awkward teacher moments_Bored Teachers 4 

"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"

awkward teacher moments_Bored Teachers 5 

"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."

awkward teacher moments_Bored Teachers 6

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."

 awkward teacher moments_Bored Teachers 7

"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 teacher moments_Bored Teachers 8 

"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 isnt" 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?"

awkward teacher moments_Bored Teachers 9 

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

11. "It's going to be a while."

awkward teacher moments_Bored Teachers 10 

“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.

awkward teacher moments_Bored Teachers

13. "It went back in."

awkward teacher moments_Bored Teachers 11

"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."

awkward teacher moments_Bored Teachers 12

"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."

awkward teacher moments_Bored Teachers 13 

"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 emphasised the "No". Oh God I still cringe.


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


next button

Other Posts You'll Also Love:12 Months In the Life of a Teacher12 Months In the Life of a Teacher

27 Teacher Problems That Will Make You Laugh Out Loud27 Teacher Problems That Will Make You Laugh Out Loud

How To Do Your Grading Like An Experienced TeacherHow To Do Your Grading Like An Experienced Teacher

Older Post Newer Post

  • Natalie on

    My awkward moment is, when I ask my studet: find the G-point (I teach math and geography) :D

  • Jennifer on

    In my first year of teaching I noticed a 20 something guy hanging around outside the classroom. I asked my class if it was someone’s relative. R. put his hand up and said " Yep. That’s my uncle" " Is he here to pick you up early? " " No, miss. He’s waiting for you " " For me ? " " Yes he’s waiting for you to go on a date with him". " Huh?" " Well, he paid me $10 to ask you out so I told him you said yes!"

  • Sam on

    Me and my boyfriend where going to mak sundaes for dessert, went to the supermarket for chocolate fuge and wipe cream, while in there go wine. At the checkout line ran into my 3 yearold student parents, the mom gave looked at me and my boyfriend and all she said was “ Have a fun night” i wanted to die!

  • Staci on

    I once had a female student have a monthly accident and rather than walk out with a jacket or something covering her. She decided to scoot out of the room on her bottom so no one would see the stain, well she left a trail and I had to call the janitor.

Leave a comment

Please note, comments must be approved before they are published



Sold Out