The 45 Cringiest Text Conversations That Have Ever Been Screengrabbed

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Screengrabbing messages is truly one of the best methods to capture those conversations that otherwise would seem unbelievable without proof. These exchanges truly are so cringe-worthy that they had to be screengrabbed and shared to really soak in all the weirdness.

From uncomfortable to awkward to downright creepy, these screengrabs are sure to make you want to make you laugh, wince from weirdness and maybe throw up in your mouth a little bit.

This might be the first almost-proposal to be screengrabbed in Facebook history. Is there an extreme dislike button for this whole conversation?

Moms are the worst with texting, and this just proves it. She’s right, though, it could have been way worse. Glad there were no pictures involved.

“How did you guys break up?” “Oh she sent one too many dancing minion gifs. I just couldn’t take it anymore!”

Uhh…I don’t think I want to know what a nut shower is anyways…

I’ve done my absolute best to uncover the truth about this convo (some light googling), and I can’t tell if the Washington Capitals made a mistake or if they’re trying to make some kind of joke at this girl and her dad’s expense. Either way, it’s a very strange tweet from a hockey team.

They say you should quit while you’re ahead, but what do you do if you’ve literally never been ahead? This conversation was DOA from the jump.

This is a pathetic attempt by a dude to break up his ex’s new relationship, and what’s funny is, he doubled down again and again. She had the Snap proof my man! Let it go!

I don’t know a lot about women, but I do know they like hearing sad-sack guys whine about how “striking out.”

Hey bud, we’ve all been there. I know when I drink too much and text, I too use perfect capitalization and punctuation until I’m called out for my bad behavior.

If you ever have to ask the question “too weird?”, go ahead and assume that yes, what you’re doing is too weird.

Listen, this is a very funny little comic that I’m sure this dude’s family group chat would have enjoyed literally any other day.

I wish I could Venmo this guy some money just to cement the fact that he is brilliant and I am his lesser.

I do not care for the implication that this man’s mother could not have sweet, ripped pythons from lifting all day every day, brother.

One cool thing some people do is yell at other people for liking something they also like. Yes, that is a good and reasonable thing that regular well-adjusted people do.

So actually, it was a completely reasonable response. Maybe she would’ve been happier if he’d sent her a sad face emoji? You know, just so she’d know she’d hurt his feelings?

“Grandma, how did you meet Grandpa?” “Well, he got horned up for me in a professional context and then I waited 45 minutes for him to take communion before I texted him and then we fell in love forever.”

You know what they say — time is money. Only in this case, we can go ahead and replace “money” with “the feelings of other human beings.”

This is actually a very sweet move from the Service King. And now that car will be named “Hannah” long after the relationship with the other Hannah (“People Hannah,” as she is now known) has run its course.

Just looking at these weird emoji cartoons is hard — imagining if they were also delivering heart-breaking news? Nothing could be worse.

Poor guy got rejected, and instead of taking the L like a man, he attacked the guy who had the fake number he was given. This is truly the saddest story ever told.

I have to imagine the first person in this convo was making a joke about something thy noticed in their online dating profile. And then, when it flew over this poor meme-maker’s head, he went in on his deeply-held ideology that only he, a king among men, is capable of putting funny lines in Impact font on the top and bottom of pictures of SpongeBob.

Wow, that mom has to be just sitting alone, in the dark, in her living room, contemplating every choice she’s made in her life that lead her to make this fateful mistake.

This is the beginning of the most fascinating story ever told, and I am right there with this guy — I want to know it all. This is what it feels like when a new trailer comes out for a Christopher Nolan movie.

If I’d known it was this easy, I wouldn’t have been so depressed the entirety of my time in college!

What part of “please don’t text me today” did this person read as “I should send one more text explaining myself”? Just stop texting, bro.

The fact that the iPhone user has a picture for this toe-texter in their contact implies that it’s not a random wrong number. This is someone they know. Someone who legitimately wants to lick their toes, got called out, and tried to back out. Not buyin’ it, toe-texter! Not! Buyin’ it!

Everything that’s happening in this text thread is not just weird — it’s positively inexplicable. It feels like an alien’s first draft of a story about people.

What, you think you can like my boyfriend’s pics just because your parents are siblings? No no no, you gotta ask your cousin’s partner before you go doing anything like that.

“Please only message me the specific information I’ve decided after-the-fact is relevant, and nothing more. I don’t have time for all this excess data despite the fact that I am writing you an insanely long text message. Thank you.”

There is nothing more cringe-inducing than someone being acting like a faux-Joker “merry prankster” online, and there is nothing more likable than a reasonable person replying normally to a faux-Joker “merry prankster” with level-headed responses.

Imagine being upset that you lost a Facebook friend. Honestly, I get upset when I GAIN Facebook friends — one more person to go back and forth on as to whether I want to invite them to my birthday party.

This is maybe one step away from role-playing with asterisks, which is objectively creepy. Also, don’t ever say you’re a “silly dude.” If you really are a silly dude, we’ll know.

If you know someone who’s lost their mom, you’ve got to make a real big mental note — we’re talking 48-point font in your head — not to bring up moms ever. Not ever.

For anyone who’s ever experienced online harassment, this has to be the dream scenario, right? You insult them back so harsh that they just plead for mercy? I honestly might print this conversation out and get it framed.

Well okay that’s one way to address rejection.

My cringe meter is on overload! This could be the worst thing I have ever read in my life!

Oh shoot this got weird. Can we all just agree that commenting on “toe color” is just a weird thing to do online? It just never comes across as normal. Ever.

Talking about pain tolerance as a pick-up line probably isn’t the smoothest decision. I think I’m mostly cringing just because that does sound super painful and I am a little impressed that he can handle so many injuries.

Oh no. Family therapy on Facebook. Everyone look away.

I will never be able to forget this idea. So much cringing.

Well this is new. The god of Facebook? I did not know that was a thing. It sounds miserable, though. No sleeping? Only eating once a week? I would hate that life. God of cringe sounds more fitting for sure.

At least he’s honest! What a guy.

Wow, he got in a relationship fast! What a smooth transition.

So much shame…but hey, at least they asked for forgiveness! Just a classic, weird, cringey miscommunication.

Nope. No. Never. So much cringing. Run away!

Adding “lol jk” to the end of a comment like that does not make anyone laugh or make it less creepy. That’s just a fact.

Wait, was this supposed to make someone want to date you? I think it has the opposite effect.

Did he just offer himself to be…pet like a dog? That is the worst thing I have ever heard. Don’t compare your hair to a dogs, it’s just too weird.

Rad. So rad. Thanks for that update.

Yes, blame your cringiness on the cold weather, that could work!

He’s an instructor…for an ethics class? I feel like he isn’t the most qualified person to be teaching that subject.

What are you doing? What is going on here? Why are you petting me?

No one wants to read this conversation. And please leave puppies out of this!

I think that actually makes it weirder. That poor cat probably doesn’t want to be talked to like that either.

Something must have been in that meatball sub because this guy is seriously tripping. I feel like I might become a vegetarian after reading this.

Oh ok well…that’s one way to tell people that your grandmother passed away.

Boilogy? Birch? Sexism+bad grammar= ultra cringe.

No one wants this. No one.

This escalated quite quickly. Who knew so much commitment could be found on Facebook.

Shoot! 68 point word! That really makes up for the fact that you just made the cringiest transition out of this conversation, good job.

It feels a little late to pull the whole “wrong person, whoops” excuse, but hey, at least they weren’t rude about it!

Considering Cleveland is like two and a half hours away from Pittsburgh, this really is a whole new level of desperation.

This guy is his own cheerleader and has no shame about it. If you can’t agree with yourself then who will?

Well that is one way to get your point across. No sugar coating, no flattering, just straight up honest. It didn’t work though so I guess don’t take tips from this guy.

This one made me almost spit out my coffee. Yes, let’s skip dating and go straight to marriage! Wow that was fast. How do you even respond to this one?

Someone send him Christian Grey’s number because this is fifty shades of really weird.

Autocorrect: always making things weirder, for everyone. This one is worse than it needed to be.

Well the Mischief Kings do sound pretty bad, maybe you do want to stay away. Plus, our parents always warned us about those bad boys!

I always love a good, “LOL, but seriously” especially about something awkward. I guess this is one way to tell someone you have an STD.

Wait, what are we even talking about here? This is too metaphorical for me, and I’m a writer.

This transition is definitely unique. Speaking of snacks, how do you feel about abs?

Two words: control issues. Stay far, far away from this person.

Inner monologues are supposed to remain as inner monologues, not be used as pick up lines. Nice try though.

This is just too weird, truly. I don’t know how people think this is a successful approach to asking someone out.

Damn, if it is bad, it just got worse, just like every single screengrab above.   Share this article with your friends who thrive off of cringiness and awkwardness. It’s always fun to laugh at these screenshots and be thankful it’s not you.

They say you should quit while you’re ahead, but what do you do if you’ve literally never been ahead? This conversation was DOA from the jump.

This is a pathetic attempt by a dude to break up his ex’s new relationship, and what’s funny is, he doubled down again and again. She had the Snap proof, my man! Let it go!

I don’t know a lot about women, but I do know they like hearing sad-sack guys whine about how “striking out.”

Hey bud, we’ve all been there. I know when I drink too much and text, I too use perfect capitalization and punctuation until I’m called out for my bad behavior.

If you ever have to ask the question “too weird?”, go ahead and assume that yes, what you’re doing is too weird.

Listen, this is a very funny little comic that I’m sure this dude’s family group chat would have enjoyed literally any other day.

I wish I could Venmo this guy some money just to cement the fact that he is brilliant and I am his lesser.

I do not care for the implication that this man’s mother could not have sweet, ripped pythons from lifting all day every day, brother.

One cool thing some people do is yell at other people for liking something they also like. Yes, that is a good and reasonable thing that regular well-adjusted people do.

So actually, it was a completely reasonable response. Maybe she would’ve been happier if he’d sent her a sad face emoji? You know, just so she’d know she’d hurt his feelings?

“Grandma, how did you meet Grandpa?” “Well, he got horned up for me in a professional context and then I waited 45 minutes for him to take communion before I texted him and then we fell in love forever.”

You know what they say — time is money. Only in this case, we can go ahead and replace “money” with “the feelings of other human beings.”

This is actually a very sweet move from the Service King. And now that car will be named “Hannah” long after the relationship with the other Hannah (“People Hannah,” as she is now known) has run its course.

Just looking at these weird emoji cartoons is hard (they are kind of weird and gross). Imagine if they were also delivering heart-breaking news? Nothing could be worse.

Poor guy got rejected, and instead of taking the L like a man, he attacked the guy who had the fake number he was given. This is truly the saddest story ever told.

I have to imagine that the first person in this convo was making a joke about something thy noticed in their online dating profile. And then, when it flew over this poor meme-maker’s head, he went in on his deeply-held ideology that only he, a king among men, is capable of putting funny lines in Impact font on the top and bottom of pictures of SpongeBob.

Wow, that mom has to be just sitting alone, in the dark, in her living room, contemplating every choice she’s made in her life that lead her to make this fateful mistake.

This is the beginning of the most fascinating story ever told, and I am right there with this guy — I want to know it all. This is what it feels like when a new trailer comes out for a Christopher Nolan movie.

If I’d known it was this easy, I wouldn’t have been so depressed the entirety of my time in college!

What part of “please don’t text me today” did this person read as “I should send one more text explaining myself”? Just stop texting, bro.

The fact that the iPhone user has a picture for this toe-texter in their contact implies that it’s not a random wrong number. This is someone they know. Someone who legitimately wants to lick their toes, got called out, and tried to back out. Not buyin’ it, toe-texter! Not! Buyin’ it!

Everything that’s happening in this text thread is not just weird — it’s positively inexplicable. It feels like an alien’s first draft of a story about people.

What, you think you can like my boyfriend’s pics just because your parents are siblings? No no no, you gotta ask your cousin’s partner before you go doing anything like that.

“Please only message me the specific information I’ve decided after-the-fact is relevant, and nothing more. I don’t have time for all this excess data despite the fact that I am writing you an insanely long text message. Thank you.”

There is nothing more cringe-inducing than someone being acting like a faux-Joker “merry prankster” online, and there is nothing more likable than a reasonable person replying normally to a faux-Joker “merry prankster” with level-headed responses.

Imagine being upset that you lost a Facebook friend. Honestly, I get upset when I GAIN Facebook friends — one more person to go back and forth on as to whether I want to invite them to my birthday party.

This is maybe one step away from role-playing with asterisks, which is objectively creepy. Also, don’t ever say you’re a “silly dude.” If you really are a silly dude, we’ll know.

If you know someone who’s lost their mom, you’ve got to make a real big mental note — we’re talking 48-point font in your head — not to bring up moms ever. Not ever.

For anyone who’s ever experienced online harassment, this has to be the dream scenario, right? You insult them back so harsh that they just plead for mercy? I honestly might print this conversation out and get it framed.