These are the kind of moments that keep you up at night.
Max Keeble, Much?
“Back when I was 15, I was leaving Ireland to move to the UK, and I admitted to my friend that I’d been in love (I was not f_cking in love at all, but I thought I was) with this girl in our class. She was all I ever thought about. As I was moving, I knew I would never see her again but for some reason I wanted her to know how I felt, but I couldn’t tell her myself. So I wrote a cringy note and left it in her bag one day, then a few days afterwards, I texted my friend, telling him to tell this girl that I love her and will miss her very much. He texted back, saying he showed the text to her. Her reaction was apparently not good at all. I felt like complete sh_t but then, whatever, I was moving away. One year later we f*cking moved back. I was back in the school, back in her classes. Yeah I kinda never said a word to her for the next 3 years. I still hate my 15 year old self. (Source)
‘A Very Dominating Woman’
“We used to have weekly 20 minute ‘silent reading’ sessions during my freshman year of high school, where we brought in a book of our choice. One time, after the 20 mins were up, my teacher had us go up to the whiteboard in turns and write down one word we came across in our reading that we were not familiar with. I wrote ‘dominatrix.’ To this day I seriously can’t remember what book I was reading. Definitely wasn’t anything pornographic. My teacher did answer! After doing a double take and pausing for like twenty seconds to collect his words lol. He told me it was a ‘very dominating woman’ and left it at that. Looking back at it, I feel bad for the position I inadvertently put him in. Generally not something any male teacher wants to explain to a 14 year old girl.” (Source)
Insert Foot Into Mouth
“I was working backstage in a production of The Addams Family (the play.) I asked the girl playing the old lady if the effects makeup they used to make her teeth look all old and gross had a funny taste. They hadn’t put any makeup on her teeth.” (Source)
Who Could Forget?
“In middle school I attempted to seriously convince a crush that I was a vampire. We briefly reconnected earlier this year. She remembers. I ‘don’t.’ (Source)
What Were You Thinking?!
“In 10th grade, a very attractive and nice girl in my French class who I had gotten to know over that year asked me if would I like to leave class early with her and hang out. I don’t know what I thought I was going to do if she didn’t ask me, but in the moment I simply replied, ‘Why would I want to do that?’ I remember she looked crushed as she walked away and the guy who was sitting in front of me turned to look at me and shook his head in disappointment. She and I never really got along the same way after that. I’d love to go back and just say yes or to still be in touch with her today.” (Source)
Surprising Nobody Caught That
I grew up in a very white, very rural town. When I was in school, people from our town (because of the town name) were frequently referred to as ‘Beaners.’ I had ZERO CLUE this was a racial slur, and assumed it was along the lines of being called a ‘Yankee’ as a northerner; not friendly, but not profane. ANYWAY, a beloved (and coincidentally Latino) faculty member passed away pretty unexpectedly, and I wrote a tribute to his life, which was read at his funeral and published in various places that included the phrase, ‘For the man who made “Beaner” a compliment.’ I meant it in the way that his excellence gave value to our town, with zero irony, and was well into to college before I realized my mistake. And no, nobody corrected me. (Source)
There’s No Recovery From That
“I stole a handshake from a guy walking right behind me. Not a wave, not a high five, a f*cking handshake. I just grabbed his hand and looked at him, then he looked past me. I turned around and there was another guy just standing there perplexed with his hand out. The only thing I could do was walk away without saying a word.” (Source)
How Does One C*ck Block Themselves Naked In Bed
“I said ‘I love you’ whilst naked in bed with a girl I’d had a handful dates with. As the words were coming out of my mouth I was praying for a stroke. I started that day a virgin. I ended that day a virgin. I was 22.” (Source)
Just…Why?
“One of my best friends had a radio show on our university’s station. I liked a guy in one of our classes and my friend and I thought it would be clever for him to interview me (off air) about my interest in that guy. We put the interview on a disc and gave it to him. The feeling was not mutual. I graduated five years ago and I’m married now but this still makes me cringe so hard.” (Source)
Bro…
“I was at a club, and the part we were at was kinda lame. So I was a little drunk and walked over to what seemed like another room in the club. I am walking with these three girls behind me and as I am crossing over to the room, this other guy is walking opposite to me. We kinda do that stupid dance when you run into someone in the hallway or whatever. I laughed, so did he, then I thought ‘why the f_ck isn’t he out of my way yet?’ Then I noticed he was wearing the same shirt as me. It was a f_cking mirror.” (Source)
Hopefully The Parents Weren’t There…
“We had a fundraiser in elementary school for the Easter Seals and the top people got Knicks tickets and got to meet a knick for a day. Gerald Wilkins called me over in front of 100’s of people that afternoon and I asked him into a microphone why all basketball players were black. Everyone laughed, including him, but I still can’t believe I asked that.” (Source)
The Second-Hand Cringe Is Real
When I was a young kid, my family was sitting around talking about a relative and how humorous she was. They always kept saying how she was always ‘Goofing off.’ I suddenly got the bright idea to contribute. So I entered the conversation by saying: ‘Or jerking off!’ I somehow got the notion that jerking off meant being a jerk — I had no idea what it really meant and I had probably never heard the phrase before. So when my family looked at me with the biggest eyes I had ever seen, I tried to back it up by saying, ‘You know? Being a jerk?’ Eventually, my aunt realized that I didn’t know what it really meant and said, ‘Uh, yeah.’ Then the silence arrived. I still cringe to this day. (Source)
Love Ya, Boss!
“My first big meeting at my job with all the head honchos…and I had to leave to go to a doctors appointment. I was so nervous about walking out of the meeting, I actually said to my boss’s boss ‘good night, I’ll miss you!’ My boss found it hysterical and told me I turned bright red as I shuffled out the door.” (Source)
Dude…
“I accidentally went to school high-school in black face. It was Halloween and I was trying to be a silhouette from those old iPod commercials where all you could see was the head-phones and the chord. I got sent home by 10am.” (Source)
C’Mon Man, It Doesn’t Get Much More Obvious Than That
“Went over to my crushes house to study. After studying for a bit I put on a hockey game and ordered us a pizza. After we ate and studied some more she invited me upstairs to go to bed. I said no I’ll just stay down here and watch the rest of the game. Realized about a week later I was invited to my crushes bed but turned it down for hockey. Yes I am Canadian.” (Source)
In His Defense, The Search Bar Is Wayyy Too Close To The Status Bar.
“That time I wanted to stalk my crush on FB while I was drunk and ended up spamming my crushes name all over my wall in different spelling variations.” (Source)
Can I Have Some M&M’s, Bestie?
“When I was in 6th grade I used to call a girl every night after dinner for like a year. I thought we were best friends. One day at lunch I asked her if I could have some of her M&Ms and she said ‘Yes, if you stop calling me.'” (Source)