‘I Sent A Sext To My Step Dad’: People Share The Most Cringeworthy Things That Still Keep Them Up At Night

by 12 months ago

There are one or two moments in every man’s life that his brain simply cannot shake. And I’m not talking the hot sex sessions that a guy wants to maintain in the portion of the brain responsible for the Spank Bank. I’m talking about the moments that make you want to crawl into a dark hole and wait to die. The super embarrassing ones, like that time I shit my pants in public. Or that rat tail phase. I suspect our brains keep them around as a growing mechanism, to remind us to never return to that place. It serves a functional purpose, but I wish I could just tell my brain I’ll never again frost my tips.

Unfortunately, I do not have that power. And neither do these people I’ve listed below who have answered the question that Redditor matthewdude2 posed:

What cringy thing you did in the past still keeps you up at night?

Here are the most cringe-worthy response.


I was really sick one day in high school, and my mother thought I was faking it and still made me go. I sneezed so hard I shit myself. It was everywhere. I called her to ask if she could pick me up from school or at least bring me a change of clothes, she still thought I was lying.

Luckily my gym teacher found me a pair of pants, but I had to deal with my shame for the rest of the school year. I got made fun of a lot for that.

That whole ‘Momma knows best’ mantra is a croc of shit. Literally. 


When I was 17 I was texting my boyfriend and remember saying “I can’t wait for you to come over this weekend so we can have sex and eat crabs”. I sent it to my step dad.

Sex, crabs, and step dad should never be used in one sentence. 


Last year on New Year’s Eve I was at a big bar in New York with friends and I got kind of drunk and went outside for a cigarette at one point. I must have actually been outside for the countdown, because when I came back in I looked at my phone and it was like 12:02 and I asked my friend why there wasn’t a countdown done by the DJ. I couldn’t really hear what he said, so I went up to the DJ and asked to use the mic and I did a second countdown. In front of the entire bar. With hundreds of people. Starting at “30”. And no one joined in.

Cigarettes kill. Self-esteem.


During my alcohol phase I went on Facebook to search for and pore over pictures of my crush. When I woke up in the morning, I realised that I had actually created an event with her name as the title.

I believe the event was set as public. The name I put was a short version of her first name, but everyone knew. We’ve never spoken since, and the last time I saw her on the street I hid.

Congrats for not murdering yourself. 


There was a brief time in middle School in which I would speak in the manner of Tony “Scarface” Montana. “Shot da fock up, you pile o cockaroches!” So embarrassing.

Just like Borat, don’t be that guy.


My crush came to my house to do a high school project. It involved the Internet and while she sat next to me she tried to navigate to Google on my computer. Unfortunately, the address bar auto-filled and took her to my last Google search… page two of results for her name. Every link had been clicked. We both just sat in silence.

No one is above a deep creep. Shoulda used Incognito tab.


I openly considered myself as a Juggalo, and had the Coolio hair style to match. I am a very pale ginger.

…Cold sweats and stifled vomit come with these memories.

You went full Juggalo. Never go full juggalo. 

[h/t Reddit]

TAGScringeworthyembarrassing moments

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