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24 Most Embarrassing Text Messages People Have Ever Sent

24 Most Embarrassing Text Messages People Have Ever Sent

by Ayoub Mask


1. Talking shit about a person to that same person

“Why is Steve being such a cunt?”

Steve seemed to have his own ideas.

2. Sent a text about my anus to my mom

“My anus is on fire dude, I can hardly walk…”

It took three months to convince my mother I wasn’t gay.

Never again will I eat burritos with my best friend.

3. I accidentally asked my mom's friend to be my girlfriend

I was like 13.

“Hey name want to be my girlfriend?”

But I accidentally sent it to my friend’s mom.

She even called me: “You are so cute, but I’m afraid I love someone else”.


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4. Sent my mom a text asking her to buy me a dildo

A bunch of my friends were down at the beach with me over Christmas. One of them was joking back and forth with his younger brother, sending him a text that said something like: “Next time you’re at the store can you grab some mayonnaise, cellophane, and the biggest, blackest dildo you can find? Cheers xx.”

He sent it to his mum instead, and then realized twenty minutes later. It completely threw him off our game of Monopoly, especially when she sent a smiley face back.

5. I sent a text about "cow sh*t" to the wrong person

I was buying some fertilizer off craigslist. The ad said to text the seller. So I did. “We need 10lbs of cow shit. Coming by Thursday. I’ll bring my shovel.”

Wrong, so very confused and concerned, number.

6. Asked my mom a question about to "Butt Stuff"

I accidentally asked my mom: “Do you ever wonder which women you know are into butt stuff?”


7. Accidentally sent my ex-wife an "I love you" text

I intended to send “I Love You” to my girlfriend of 14 months. I accidentally sent it to the ex-wife.

8. Sent a lube text that was meant for my BF to my boss

I once sent a text to my boss “Can you get some more lube while you’re out? I Love You.”

9. Bruised genital pics to the wrong person

My brother thought it would be funny to send me a picture of his swollen bruised junk after his vasectomy. After the third time without a reply from me, a woman called and asked why he was sending these messages to her 15-year-old daughter. He’s lucky he didn’t get arrested.

10. A smiley face at the wrong time

Embarrassing but to the right person, my then girlfriend at the time had just got into a car accident and I sent her the following: “I heard you got into a car accident!? :)”

That face shouldn’t have been there…



11. Sent detailed sexual text to my mother

Thanked my partner graphically for his stellar performance the night before, including a compliment about the large load he flooded me with. Sent to my 67-year-old mom. I immediately called her and apologized. She took it gracefully, which I’ll remember when my 20-month-old daughter becomes old enough to make every subsequent holiday dinner with the family explosively awkward.

12. Accidentally sent sext to his own daughter

Texted my daughter saying that I wanted to “Fuck her so hard she forgot her name” once… Regardless to say, my wife wasn’t too thrilled.

13. An awkward situation that ended well

Not a text, but one of the managers at work emailed me and the email contained some unintentional casual racism. I meant to forward it to my friend but accidentally just replied saying “Dude look at the rampant racism hahahahaha.”

I still have my job, 9 months later.


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14. I sent sexual message to my entire friend's list

Not a text really, but I was on my 3DS last night and drew out a message with that little app saying “hi. You’re cute. Let’s bang,” meant for my boyfriend.

I hit send and it informed me the message went out to my whole friend list…. Including my younger brother, a couple of his friends and some random I traded fruit with in Animal Crossing once..

15. Sent inappropriate video to my boss

I thought I was sending my girlfriend (now wife) YouTube videos of 1-armed push-ups.

Instead, I sent it to my boss who lost his arm in a biking accident 8 months prior

Luckily, he laughed.

16. Wrong text to girlfriend's sister

“YOU FUCKING DYKE”, meant for my buddy while we were playing Civ V. Sent to none other than my girlfriend’s sister.

…who is a lesbian.



17. I managed to save the situation before it was too late

I accidentally sent some very sexual texts to my sister. Grabbed her phone and deleted it before she read it.

18. I accidentally sent naked pictures to my mother

I sent a nude to my mom… I don’t think we made eye contact for a good month after that.

19. My crush accidentally crushed my heart

The girl I was head-over-heels for (and best friends with for a time) accidentally texted me saying, “wobbysobby is a weird dude, we’re not even really friends anymore.” :[

20. An accidental break-up

“I’m sincerely thinking about breaking up with ex-gf , she’s done nothing but make me feel like shit for weeks.” Meant for best friend, sent to ex-gf.

Didn’t even have to break up after that, which was nice.



21. Confused my sister and embarrassed myself

Accidentally texted “I want you to be my baby mama” to my sister instead of my girlfriend. Never got a response.

22. I tried to buy weed from my dad

Accidentally saved my fathers number as my dealers number. Tried to buy weed from my dad.

23. Accidental hilarious text to crush

I was texting my friend and my crush at the same time… bad idea. Ended up saying, “Gandhi makes a better porn star than Martin Luther King any day of the week” to her. Whoopsie.

24. Cars and sex 

“Yeah, I loved that time too, it was really hot ;)” talking about shower sex with my girlfriend, meant to send it to her, sent it to my dad.

We were talking about washing my Chevy S10, so his response was “So you have a hot time washing that S10?”

Yes father. I did.


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VIA : Thought Catalog

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