Bored Panda
People Are Sharing Their Most Embarrassing Messaging Fails And These 37 Are Hilarious
FunnyAPR 2, 2026

People Are Sharing Their Most Embarrassing Messaging Fails And These 37 Are Hilarious

42
8
The human brain is like a machine that occasionally glitches. Sometimes, the words in your head may not come out the way you intend them to. And it could lead to a hilariously embarrassing moment that you may not be able to shake off for a while. 
Here are examples from people who experienced them firsthand. We’ve all been there, and as cringeworthy as they are, we will eventually end up looking back with laughter. 
If you’ve been in this situation recently, feel free to share your experience in the comments.

#1

People Are Sharing Their Most Embarrassing Messaging Fails And These 37 Are Hilarious
I once apologised for any incontinence this may have caused
34points

#2

People Are Sharing Their Most Embarrassing Messaging Fails And These 37 Are Hilarious
I once emailed a colleague who wasnt very tall and instead of finishing the email' see you shortly' I wrote 'see you shorty'
31points

#3

People Are Sharing Their Most Embarrassing Messaging Fails And These 37 Are Hilarious
I’m a nurse, I was writing a message to a doctor and my ? key got stuck, I sent “What are your thoughts????????????” He replied “first let’s calm down”
30points

#4

People Are Sharing Their Most Embarrassing Messaging Fails And These 37 Are Hilarious
I was texting back and forth with a guy selling a space heater online. I then started texting with a friend about the weird things we do in the doctor’s exam room while waiting for the doctor to come in. I texted “I always hide my bra and underwear under my clothes when I see my gynecologist.” I received a text back “that’s nice but are you still interested in the space heater?”
30points

#5

People Are Sharing Their Most Embarrassing Messaging Fails And These 37 Are Hilarious
once I wanted to thank my professor for his message and instead of writing "thanks once more" it autocorrected to "thanks, for once"
27points

#6

People Are Sharing Their Most Embarrassing Messaging Fails And These 37 Are Hilarious
My partner and I were actively trying to get pregnant and I had just taken an ovulation test. Decided to text him saying “want to make a baby tonight?”…sent the text to my dad.
Worst foreplay ever.
27points

#7

People Are Sharing Their Most Embarrassing Messaging Fails And These 37 Are Hilarious
I accidently sent an email it signed it off “please hesitate to reach out “ I forgot the don’t
23points

#8

People Are Sharing Their Most Embarrassing Messaging Fails And These 37 Are Hilarious
I once accidentally misspelled Kind Regards’ and unfortunate ‘t’. I work in a disability dept.
22points

#9

People Are Sharing Their Most Embarrassing Messaging Fails And These 37 Are Hilarious
I once wrote “please help me with the blow.” (Was meant to say “below” as it was a chaser email)
22points

#10

People Are Sharing Their Most Embarrassing Messaging Fails And These 37 Are Hilarious
Ugh once I emailed one of my clients on a Friday saying “have a lonely weekend” instead of a lovely weekend
21points

#11

People Are Sharing Their Most Embarrassing Messaging Fails And These 37 Are Hilarious
I had messaged my wife's best friend earlier, but later in the day, I MEANT to text my wife, "We should fool around tonight!" But, I sent it to her friend instead.
She responded with, "We should probably ask [wife] first."
21points

#12

People Are Sharing Their Most Embarrassing Messaging Fails And These 37 Are Hilarious
i once tried to email my teacher saying i was sick. my brain thought 'i am is the sickness me is not will be in asparagus' is a proper coherent sentence (im guessing i meant to say appologies at the end there) yeah i was sick af
20points

#13

People Are Sharing Their Most Embarrassing Messaging Fails And These 37 Are Hilarious
I like to write strongly worded emails to people and not send them. They get UGLY and it’s extremely therapeutic. I often times edit them over and over until my rage turns level headed. Do it. I highly recommend it.
Except don’t put their actual email address in, or don’t save them for ever and ever. Or at the very minimum don’t accidentally pocket email your last 20 drafts to unsuspecting supervisors, CEOs, colleagues, parents, preachers, and friends.
20points

#14

I accidently put in a delivery order while typing a note to "please leave order at the door" and had not added the tip yet. so it just said "please leave" with no tip. I was mortified
18points

#15

People Are Sharing Their Most Embarrassing Messaging Fails And These 37 Are Hilarious
I was replying to a customer regarding our hours… it corrected yes maam to yes mama.
16points

#16

People Are Sharing Their Most Embarrassing Messaging Fails And These 37 Are Hilarious
I once texted my boss (I’m a teacher) I had to leave early bc my 2 year old had diarrhea… accidentally just put “had to leave… had diarrhea” and put the big emphasis effect on “had diarrhea” on accident
16points

#17

People Are Sharing Their Most Embarrassing Messaging Fails And These 37 Are Hilarious
Signed “kinky,” instead of “kindly,”
16points

#18

People Are Sharing Their Most Embarrassing Messaging Fails And These 37 Are Hilarious
My husband was an enrollment counselor for a college. He messaged this girl “I am you”
15points

#19

People Are Sharing Their Most Embarrassing Messaging Fails And These 37 Are Hilarious
I work in communications and on my resume I accidentally had “excels at pubic relations” instead of public relations
15points

#20

People Are Sharing Their Most Embarrassing Messaging Fails And These 37 Are Hilarious
I’ve sent multiple emails back to back with just “hello” because I kept forgetting hitting enter would just send the email instead of skipping a line
14points
42
8