If you've been through high school, you know that some people do things that are particularly cringeworthy. Seeing those moments of embarrassment happen before your eyes are the worst — our natural empathy kicks in and we start to feel like we too have committed the grave faux-pas we're watching unfold before our eyes. That's why we so enjoy cringe-worthy posts here on the internet — with a little bit of distance, we can chuckle and shake our heads without experiencing all that icky empathy. Unfortunately, keeping those cringeworthy moments at arm's length does dilute the experience a bit. If only there were a middle-ground... a way to both really revel in a moment of cringe without having to feel the same shame and embarrassment ourselves. And that's the beauty of these specifically sad and weird cringeworthy posts — reading them is certainly uncomfortable, but it's just enough discomfort to give you the biggest possible hit of cringeworthy revelry. Enjoy!

There's a self-esteem booster.

Some girl f*cking cried because she got assigned as my partner on a school project. – Funkstramadus

True love... will have to wait.

ORIGINAL TWEET: Everyone help me find this man I saw at the football game I want to go on a date with him. THE ACTUAL GUY’S REPLY: This is me. I’m sorry but you’re not my type. – Xboxjuanlol

Just mess me up fam.

GUY ON TINDER:I love your bio GIRL: I know right! GIRL: Like if only there was a button that was for the polar opposite of a Super Like… a Super Nope GIRL: That’s what I would’ve pressed – nerdy112233


Ya hate to see it. – Wheeler_Chair

"Showing family my Pokemon collection over Thanksgiving."

Every other person in the room looks disappointed, especially the man in the back with his head in his hand. – CharmingShower

"Maybe the problem... is me?"

No one came to my loneliness seminar. – illinoisilluminati

A business opportunity goes bust.

So hey everyone I’m in immediate need of help. So back at the beginning of Summer I bought around 6,000 fidget spinners at wholesale to resell. I’ve only sold 73 of them. Does anyone want to buy some in bulk? I’m getting desperate. I sunk my life savings into this. Please help. – CorexMTA

A post on an anti-vaxx forum:

If you were 32 weeks pregnant, and your spouse posts a meme in a private group that you’re not in, that says “I only date antivaxxers because you only have to pay child support for eight years instead of 18.” What would your thoughts be? He says it’s not about me. – livingdecay

11 bags I get. But 12?

The 12 bags of trash I pulled out of my depression pit of a room. Please remember to take care of yourselves you guys. – APUSHMeOffACliff

Don't post this on social, my dude.

No one came to his party. – poppenkill

C'mon dude, read the room-- er, crowd.

That fan really wants that hug. – LSines2015

A text response to an innocuous "Happy New Year" text.

SAD GUY: Thanks cutie SAD GUY: Wanna know a secret? I’ve actually never had a New Year’s kiss. SAD GUY: May I kindly offer you to be my first? – pseudo_potatoes

He set himself up, she knocks him down.

GUY: You have the most beautiful eyes. GIRL: Ya I’m going on a date with im tomorrow night after I get off work GIRL: No you don’t know him – StarAssassin

"I have never felt more sorry for someone ever."

The headline to an AskReddit question: Wife wants to use a sperm donor because she wants attractive kids. – Aquagenie

"Finally, I'll have the time to review all my Scotch."

The headline to a YouTube video: Dude reviews Scotch while his wife packs her stuff and leaves him. – Terminator076

Why would you take a picture of that?

Found an old picture I took of the pillow I cried into, after my ex broke up with me. – foxfunk

They don't like-like him.

Put it on his gravestone. – Rhysatron004

Next time, take it slow.

No one showed up to the speeding dating event. – VoidTorcher

"This is a fun event for me, I am not sad, hahaha"

Divorce selfie. – [account deleted]

Sorry Jaime.

Must’ve wanted a different game. – WeezyMac_

Growing up is hard.

Me, my sister, and my best friend (from left to right) at our graduation trip. Fun stuff. – -NoCoolName-

The post's headline was "My shy waitress asked for my phone number by putting the request on my check."

Then, a commentor filled them in on what actually happened: Hey, uhh, sorry to break it to you but this is how places with a MICROS POS system do their to-go orders. All to-go orders have this on the check. Sorry, she’s not into you. It’s just a place for the server/ bartender to put the phone number of people calling in to place orders. – simomii

"C'mon Frank! Take off that shirt and hop in the pool!" "Haha, no thanks! Don't want to burn! That's the reason!"

I’m sure this will fix things! – manintransition

You guys have fun.

When you finally realize your group chat has gone dead because your friends made a new one without you. – _chocolatemango

But how reliable is the internet, really?

This is heartbreaking. You just hate to see it.

He's probably worried about having Watchmen spoiled.

Father sits on the couch watching T.V. while his son sits alone, about to blow out the candles on his birthday cake. – CharmingShower

Friends for-never.

I was 10 when my teacher asked us to write a short story about our best friend. I looked at mine and smiled. I was not in his story. – @pineabul

Remember when Justin Bieber got arrested? Good times.

Why does he look happier to be in jail than he was to be standing next to me? – akarim5847

His sadness level is over 9000!

So… I guess she said no? It’s a good drawing, at least.

Who's man is this? Come get your man.

I am known for creating some of the most attractive sims in The Sims freeplay. This one here is the sexiest sim I have ever created. – skane110
© Copyright 2020.