11 Hilarious & Cringeworthy First Day of School #MomFails

Wendy Robinson | Aug 2, 2016 Being a Mom

mom hiding under bookFor a lot of moms, the first day of school is one of the best days of the year -- especially if you've been home all summer with kids whining about being bored and/or filling their hours by fighting with their siblings. (I mean, hypothetically, of course. I'm sure none of us experienced that IRL. No sir.) 

But sometimes that magical and longed-for day of sending kids back to school goes seriously and hilariously wrong. 

From putting kids on the wrong bus to school uniform blunders, these 11 stories of total mom fails on the first day of school will make you laugh (and cringe).


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  • Ew!

    1
    Image via iStock.com/Debbi Smirnoff

    "My husband and I divide and conquer when it comes to getting kids out the door for school. I was loading up backpacks and put my son's lunchbox in. It felt full, so I assumed my husband had packed it. 

    Turns out it was filled with the remains of his lunch from the last day of school the year before. We'd forgotten to take it out and clean it! So, for his first day of school lunch, my kid had a mold-covered sandwich, a decomposing apple, and a bag of stale crackers. Yum!" -- Rachel L., Des Moines, Iowa

  • Sleepy Heads

    2
    Image via iStock.com/PeopleImages

    "My kids woke up with the sun ALL SUMMER LONG. Seriously, not ONCE did they sleep past 7:00 a.m. I had stopped even setting an alarm, because what's the point?

    So, OF COURSE, they all sleep in on the first day of school. I woke up 45 minutes after the first bell and found two kids still sleeping and one kid eating cereal in the backyard. Total fail." -- Andrea P., Greensboro, North Carolina 

    More from CafeMom: Type-A Mom vs. Regular Mom on the First Day of School

  • Tearjerker

    3
    Image via iStock.com/PeopleImages

    "When my son started kindergarden, I was trying my best to keep my emotions in check. I got him to his classroom with no tears on either side. And then I walked outside, and there was a group of moms talking. I walked over to them and as soon as one of them asked me how I was doing, I burst into tears. Like, fully sobbing. 

    Apparently they were all just barely holding on themselves, because as soon as I started crying, ALL OF THEM started crying too. So there were, like, 10 of us in a circle, just bawling like babies. There was a group of dads standing near us, and they looked at us all like we were nuts." -- Sue T., San Antonio, Texas 

  • There Will Be Blood

    4
    Image via iStock.com/John Sartin

    "I was driving my son to school for his first day of first grade and he decided that was the perfect time to yank out his wiggly tooth. I pulled up to the drop-off zone, turned around to say good-bye, and discovered that he was covered in blood. Excellent look for the first day of school!" -- Annie E., Tucson, Arizona

  • Mr. Handsome

    5
    Image via iStock.com/Wavebreakmedia

    "My son STILL is embarrassed by the fact that I blurted out 'You're so handsome!' to his new teacher. Whoops. In my defense, who would expect a second grade teacher to look like a young George Clooney?" -- Martha F., Saint Paul, Minnesota

  • A Little Late

    6
    Image via iStock.com/monkeybusinessimages

    "Our school has ALWAYS started on the day after Labor Day. Always. 

    Until last year. 

    We'd been having some bad winters and so I guess they moved up the start day to allow for more snow days. But somehow we missed that memo. So we took the kids camping for the last week of August like we always do -- totally off the grid, roughing it. 

    When we got back into cell phone range, we had a bunch of messages from the school. We'd missed the first day of school by a WEEK. Oops." -- Janet K., Belmont, Massachusetts 

  • No Uniform

    7
    Image via iStock.com/alexandr_1958

    "A few years ago, we moved to a new school district. When I showed up with my son, dressed in his finest hipster outfit of skinny jeans and suspenders, I learned that, although most of the district doesn't require uniforms, his school was one of the two that did. 

    I had to take him to the store and buy him a whole new outfit before he could start for his first day. He was so mad and I felt like an idiot for missing that info on all the paperwork." -- Sharon A., Tucson, Arizona 

  • The Gossip

    8
    Image via iStock.com/Tomwang112

    "On the first day of school, I saw my social butterfly daughter giggling and whispering with all of her friends. I left her and went to work, feeling good about a no-drama drop-off.

    A few hours later, I got a call from the principal asking me to come in. Who gets called into the principal's office on day one?

    Well, turns out my daughter decided to tell all the other kids in her class that she had a baby sister on the way AND exactly how that baby was conceived. Including drawing a diagram in art class. 

    I guess that birds-and-bees talk we gave her was a little too in-depth." -- Name withheld by request

  • Bus Problems

    9
    Image via iStock.com/MariaDubova

    "I put my kid on the school bus for the first time. And I put him on the WRONG school bus. He ended up at the local charter school instead of our neighborhood school. I'm still mad the bus driver didn't check that each kid was on the right bus as they got on." -- Wilma V., Arlington, Virginia 

  • Picture Problems

    10
    Image via iStock.com/frankiefotografie

    "Okay ... this story dates me a little! But I'll never forget the year that I took my daughter to her first day of kindergarten. I REALLY wanted to get a cute picture of her sitting on the steps of her new school in the little plaid dress I made for her. We got to school, I somehow managed to get her a spot right in the middle of the steps, and then realized I had a camera and no film! 

    I didn't have enough time to go buy some before school started, so I decided I'd just re-create the moment at the end of the day at pick-up. Ha! She walked out of school looking like she'd been hit by a bus! She'd gotten a fat lip from falling on the playground, she'd lost her hair bow, and her dress was covered in dirt and paint. She was a mess. I took the picture anyway but was devastated that it wasn't what I wanted it to be. I think I cried on the way home.

    Thirty-five years later and now it's one of my favorite photos!" -- Arlene F., Hastings, Minnesota 

  • Missed Connection

    11
    Image via iStock.com/Tashi-Delek

    "Due to a communication mix-up between my ex and me, nobody remembered to pick my son up after his first day of pre-K. I was in a meeting with my phone turned off and my ex was doing whatever the heck he does all day, so it took the school almost three hours to get ahold of us! 

    I was mortified but my son thought it was great because he got to stay longer at the library." -- Name withheld by request

    More from CafeMom: 25 Ways to Give Your Kid the Best First Day of School Ever (PHOTOS)

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