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Cringe-worthy Texts You Won’t Believe People Confessed To

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Can you IMAGINE sending this to your boss?

Texted my 50 – 60-year-old boss (Director of Human Resources) instead of my fiance (then girlfriend) this…

“MFW I eat the p***y so good you punch me in the back of the head.”

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.”

I turned so very, very, very red. Well played.


Give em the goods, then take it away

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


Another “boss” boss story.

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.”

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…

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.


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.


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