Hilarious and Horrible Text Message Fails That Will Make You Cringe For Eternity

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Nobody said that crafting the perfect text message was easy! And sending a poorly-worded message to the wrong person is downright mortifying. But most of us have done it at least once, right? After all, it’s not unusual to have days where your brain just can’t run at 100%.

Usually, a wrong message (like a wrong number) is pretty easily fixable. You just say something along the lines of “my bad” and call it a day. But some texts are so utterly awful that they’ll follow you around for a good long while afterward. Want an example? Then keep reading, because the texts below will actually surprise you with how horrible they are — and have you in stitches!

After drunkenly making out with a co-worker, I sent a hungover text to apologize and make sure we were both clear it was a mistake none of our coworkers have to know about. I sent it to another coworker with the same name. My god, the office gossip… Lumpyalien


My brother and I were flying back from my other brother’s place. He’s sitting next to me on the plane and I get a text from him:
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“I can’t wait to be inside you”
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spacelincoln


Something like, “he passed away early this morning, it was sudden, the doctors say it was in his sleep and peaceful.”
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It was supposed to be to my wife about a friend’s dad who died.
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Instead, I sent it to one of my brother’s who asked, “have you talked to him lately?” about our other brother a couple of days before, and I hadn’t answered.

So he got the text, and then no follow up from me cause I was running around, and phoned me like 10 times. I felt so bad for scaring the sh*t out of him.billbapapa


Texted my 50 – 60-year-old boss (Director of Human Resources) instead of my fiance (then girlfriend) this…
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“MFW I eat the p***y so good you punch me in the back of the head.”
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I immediately apologized, tried to play it off as my friends grabbed my phone, etc. etc.


She never responded. She never brought it up. Until I came to work following the day of my engagement, and my boss looks at me, places her fist on her head, and says, “Well, we all know why she said yes.”
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I turned so very, very, very red. Well played.
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JeffreyGlen

I sent “I love you” to my girlfriend. Then told her “wrong person” as I meant to send it to my mother.mdenglish


Many years back. Was flirting with this girl and was feeling the situation out as to if she was interested. I’d very recently started a new job (about a month in) and my vice president’s name was “Scott.” The girl I’m flirting with is named “Samantha.”
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She had to cancel going out for drinks with me earlier that day and I ended up with some other friends – got right wasted. She had texted me a bit later in the night saying she was really sorry and would have to make it up to me…
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So, here I am in a cab. 2 am. Wasted. Looking at the text and think this is a smooth reply… “You’ll just have to make it up to me with a few hags and kisses.” Yes. HAGS and kisses.
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Smoooooooooth.
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Now, it would be cringe-worthy on its own, but instead, I’d accidentally flipped back to the convo with my VP and sent it to him.

I get a reply “I think this might not be for me, but it sounds like you’re having a good night. See you Monday!” Stomach dropped and I figured I’m screwed. Came into the office Monday and my VP comes over and asks if I got my hags and kisses. 8 years later, he still brings it up from time to time. Amazing.ilovedillpickles

Not me, my sister. She once texted me (instead of her husband) about how amazing her masturbation session was.Alateriel


Texted my friend that I’d call her back after I was done pooping but I “ate White Castle the night before so it may be a good while.” I even put the little poo emojis at the end of the text.
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Sent it to the painter I had been corresponding with all day who was actually downstairs starting on the kitchen. I wanted to die…


It was a Mexican Standoff.
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I sent him an after text that just read “Please mail me the invoice. Sorry about that” and hid upstairs until he left. So much shame.
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doc_sluggo


“Hope you’re naked when I get there.”
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Sent to my son’s daycare provider; she’s 65 and 300 pounds.
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Intended for my wife of the same first name.
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The daycare lady handled the text well.
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“You don’t want me to be naked. I’m glad you guys still have a spark.”
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gobigred3562

I sent my wife a rather explicit text message on my phone whilst also typing a message to my friend on the computer. Thought I made a huge mixup and texted my wife “sorry wrong person.” Realized my mistake when she responded, “Who was it supposed to be for?!?!”


Funny enough, I responded that it was for my friend and she was at first like “Oh, ok.” But then a second later she was like “What!?” in regards to the first, explicit message.
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I gave up after that and just called her to explain. Was way easier. Texting does not convey meanings very well, no matter how many emojis you put on them.
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paulguise


My phone doesn’t save names on some occasions and instead, only saves numbers, so I know contacts by the last three digits.
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My girlfriend’s number ends in 838, my girlfriend’s step dad’s number ends in 838.
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I sent him a message simply saying, “heading off to bed now, will talk to you tomorrow, love you x…”

He replied with “I love you too, but I think you should also tell Alice that just in case she gets jealous.”TusShona Good thing this parental figure had a sense of humor!


I texted my boss
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“Hey slut, how’s the truck stop treating you?”
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He texted back, “LOL”
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I am surprised my boss took it as well as he did.
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It’s not the first time I called him “slut” in a text meant for my sister.
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I probably should start calling my sister something else.
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– nativehoneybaby


I somewhat frequently text my Marines, both subordinate and superior, “I love you,” instead of the wife.
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And yes, most of the time they just text back, “I love you too.
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VerdeGringo

Not as embarrassing as the others here, but I meant to text my wife that “we will go clothes shopping after I get off work” but I sent it to my boss. He just texted back “OK, but I gotta usher at mass first.”earnedmystripes

I once sent “don’t be a little b*tch” to my attending physician (as a medical student). It was meant for my brother but the attending had just sent me a text saying he was running late. Luckily he laughed it off, but I almost died.AbsoluteSilence

Not a text, but about 15 years ago, I worked in the corporate office for a bank in Charlotte. A buddy of mine also worked there and we’d email insults to each other all day because we were bored. And when you work in offices, you get emails all day from higher-ups about nonsense. So, you see where this is going. I emailed the head of the HR department accidentally and said his wife blows goats. It was a wonder I wasn’t fired immediately.Bmac1977

Earlier I meant to text my boyfriend “I see you!!” I accidentally sent it to my sorority sister and immediately told her that I sent it to the wrong person and she replied back “okay, I was a little creeped out because I just stepped out of the shower”buhrandee


My BFF is a girl I’ve known for 20 years, over 20 if you count BBS chats. There has never been anything sexual between us, we just have similar senses of humor. Also semi-relevant she’s a little white girl I’m a big black dude.
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Post-divorce I finally came outta my funk and started chatting up this girl at work also a little white girl and a bit submissive, I had a bit of a buzz and things had moved to sexting.
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I was also chatting with my BFF at the same time, got the bubbles backward and sent something along the lines of “so how much longer you gonna make me wait? I wanna pin your little white a** to the bed and make you scream into your pillow.”

My friend sends me back a pic of one of her cats laying on her pillow with “will this p***y work?” as the caption. Her husband sent me another picture of one of their other cats on the couch asking about this p***y instead. I ended up getting cat pictures all night from both of them.tdasnowman

I once sent a text that I thought was going to my wife. It wasn’t near as explicit as most of the texts I’ve sent her, but it still talked about wanting to have sex later. I heard my phone buzz a minute or two later and had gotten a text back saying “I don’t think this was meant for me” from my mom. 

I was so embarrassed and immediately texted back saying I was sorry and she was correct in assuming it was for my wife and not her. The next text back was the worst part, she responded “don’t worry, it’s ok. Your dad also sends those types of messages, mostly while he’s at church.” Was too embarrassed to tell my wife and my mood was killed so I just smoked a cigarette and went to bed. It caused me to add a heart emoji in front of my wife’s name so that I knew not to send those messages without seeing the heart emoji first. Still, have never mentioned it to my wife and have not told anyone about it. – Deleted User

“Dad was being a pain in the ass again, careful when you get home.” Sent to my Dad.Give_Me_Your_LSD


“So how about a lap dance for the birthday boy” sent to my sister accidentally, on my birthday.
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She still brings that up every now and again.
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Outrageous_Claims

I accidentally sent a picture of my erect d*ck to my dad.Sasquatch_000


This was right when Smart Phones became a thing, and I was a bit late to the party because of when my upgrade was scheduled. So, I had just gotten a new smart phone, wasn’t fully acquainted with all of the new/different features, and I was pretty drunk one night.
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Remember how on old cell phones you could send a mass text and no one would be any the wiser? Well, I sent out a mass booty call text to like twenty girls on my phone, thinking it was twenty separate messages.

Instead, it was my first experience with a new thing called a “group chat.” So that was really awkward. My friends still talk about it, lol. Good times. The worst part was that they all started talking to each other. About me. I felt like Adam Sandler in wedding singer when he’s singing about Linda.Eltotsira

LPT: if you catch that you’ve texted the wrong person on an iPhone before the text had gone all the way through, quickly swipe up and put your phone on airplane mode. You’ll get an error on the text that it never sent. You can now delete it.Pulmonic Love these horrendous text fails? Stay tuned for the worst fashion fails of all time…