Funniest Mistake Texts

Funniest Mistake Texts

Funniest mistaken text messages contest results.

Thanks everybody.  We received thousands of entries, all of which were hilarious, showing us the perils of the digital communication age.  Sometimes you hit send before you check you you’re sending it to.  These are the funniest ones with their responses once the sender realized the error.

Fifth Place, Prize — lifetime subscription to the Dingle.

Jeff Derthins, Bismark South Dakota, sent us this one:

I received the following message a few minutes after I texted my boss about some work stuff.  She is a pretty good looking 29 year old blonde, who is married to a personal trainer.

“Honey, if you’re done doing squats come home and I’ll squat on you.”

I replied, “Really?”

She sent me the red-faced emoji a few minutes later.  “OMG, sorry, that was meant for Chris, obviously.” 

“Darn,” I replied.  The office had a good laugh about it the next day.  We all started pantomiming squat exercises and looking at her lasciviously.  She fired me a few weeks later.


Fourth Place, Prize — lifetime subscription to a good web site.

Geraldine Springer, Boston, New York got more than she bargained for with her boyfriend’s text:

My boyfriend at the time sent me this one, thinking he was sending it to one of the guys in his crime ring, the safe-cracker, Jerry.  I understand how he made the mistake, I’m Gerry with a G.

“Listen, asshole, if you can’t crack a safe in less than three minutes why the hell should I split the takings with you.  You’re getting three thousand, if you don’t like it talk to Mr. Smith and Wesson.”

Then there was an emoji of a gun.  I sent him back a text saying, “Honey, wtf?”   All he replied was “Woops.”  That was an awkward night at Red Lobster.  Halfway through desert I broached the subject.  “Honey, I thought you were an insurance salesman,” I said.

“Yeah, well, that was a euphemism.  I thought you understood.”

“A euphemism for leader of some kind of Oceans 11 crime ring?”

“Pretty much, yeah.”

“And I should have gotten that from insurance salesman?”

Needless to say we broke up.  He and his ring got caught a few weeks later trying to rob a casino on the Gawanda Indian reservation.    He’s doing thirty years in Attica.

Moral of the story, when someone tells you what they do for a living, always ask them, “Is that a euphemism for something else?”   You never know.


Third Place, Prize — lifetime subscription to O Magazine.

Oprah Winfrey, Montesito, CA, submitted this chuckler:

I got this text from Stedman.   “My girlfriend might be running for president.  What will that make me, first lady?  I can’t wait to do you in the Lincoln bedroom while she’s in the situation room putting her finger on Gale’s button.”

Stedman, he’s such a little slut.


Second Place, prize — lifetime subscription to Prison Quarterly

Melania Trump, New York City, sent us this one:

I got this text from Donald.

“Vladmir, thanks again for all your help stealing the election from crooked Hillary.  Couldn’ta done it without you.  I owe you big time.  Oh, and I can’t wait for my next trip to Moscow to do some more of that dirty dossier stuff.  Better keep it cool for a few months though till it all blows over.  Meanwhile, do what you want in Demascus, we’ll lay off.”

I didn’t know what he was talking about so I ignored it.  But now, looking back, it really makes me wonder.


First Place, Prize — lifetime prescription to Xanax.

Donald Trump, Miralago, Florida, this soon to be Nobel Peace Prize winner also takes our Grand Prize.  Good job, Donald:

I got this text from Rocketman.  I think it was meant for his lieutenants or something.  Surprising that they communicate in English.   Woulda thunk North Korean.

“Lieutenant, everything’s going according to plan.  We’ll launch the nukes at New York, Washington and Seoul as soon as that idiot Trump signs the accord.   Then I will rule the world and won’t that be ironic?  I will make you number one and Dennis Rodman my number two minion.  I will appoint myself head of Miralago Country Club and make Donald carry my golf bag.”

I replied, “Um, Rocketman what the heck are you talking about?”

Never heard back.  Strange guy.





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