35+ Cringy Text Messages That Honestly Hurt to Read

Because we’re merciful, we’re going to start the list of with a text that isn’t really that bad. Sure, “holy guacamole” is a terrible opening to try and flirt with someone, but at least this guy took his deserved rejection like a champ.

Besides, “bravo avocado” is actually pretty funny. At least he had a good sense of humor about the whole thing, which is more than we can say for most of this list.

Having somebody give you a wrong number to subtly deflect your advances is a very common tactic, and of course, nobody is happy to be on the receiving end of it. Still, why get mad at the guy whose wrong number you got?

Moreover, what’s the deal with trying to flex on some stranger who is just as confused as you are? We don’t know what this guy is so insecure about, but it sure is sad.

Look, we’re not going to outright condemn people that do text roleplay. People are entitled to their interests. Still, it gets really cringy when you break out the roleplay without warning, with someone who didn’t agree to it.

Besides, this particular roleplay is a little creepy, don’t you think? We’d be terrified if the situation being described here came up. This is how a lot of crime show episodes start.

Sometimes, the cringe really just comes out of nowhere. When a text starts out in a pretty normal way, it can be surprising to get hit with the dreaded “asterisk roleplay”. Apparently, this kind of thing has grown quite popular recently.

Roleplay may be harmless, but it’s still really weird to pull it out on someone who had no idea it was coming. Especially if it involves crawling into their lap.

As always, we have some cringy asterisk roleplay going on here, but even worse than that, the guy sending this message doubles down with horrific flirting skills. Backhanded compliments tend to fare poorly in these situations.

Even after he misses his shot, he keeps both of these problems going, proving that this is not a single cringy incident for him: he’s just a hopelessly cringy person.

You may have figured it out by this point, but a lot of these are going to involve text roleplaying. Look, it’s just getting really trendy to do right now, for some reason. Needless to say, this example manages to be very cringy.

At least this version of sexual assault is only carried out in text, but it’s still odd that someone would just jump right into something so straightforward like this, especially with someone who is apparently not down for it.

Generally speaking, being honest doesn’t hurt. But sometimes, it really does. We suppose it depends on just what kind of questionable things you are honestly thinking. There’s a reason everyone does a little bit of lying.

This guy’s attempt to be honest unfortunately just backfired into being cringy for him. It turns out that this isn’t the kind of opener most women are looking for when trying to find someone on the internet.

At first glance, this cringy text seems pretty awful, but based on the context, it seems like these two people know each other. Because of this, it’s quite likely that our cringy friend here is just joking.

Still, if someone who claims to love you believes that it was the cringiest thing they’ve ever heard, then maybe the joke went a little too far.

Alright, so this is another cringy text roleplay. But really, that’s not the weirdest thing about it. The weirdest thing about it is the fact that this roleplayer “tipped his fedora”. Of all the hats to choose, why that?

Like, who actually wears a fedora in this day and age? Or does his roleplay also include pretending to be in a different era. Either way, this just seems like a really weird way to initiate roleplay, and that’s saying something.

Look, everyone is entitled to their own interests and feelings, but we have to be honest: the least you can do is keep some of it to yourself. Not that you have to hide who you are, per se, but at least find the right people to share it with.

We don’t know what possesses someone to pass themselves off as a wolf or something, but believe us when we say there is nothing intimidating about any of this. There’s just cringe: so much cringe.

You know, it’s not that everyone is actually trying to be cringy all the time. Sometimes, the cringe well and truly just happens by accident. For instance, when you completely misinterpret what “celebration of life” means.

But hey, cut this person some slack. If you had never heard that term before, admittedly, it does sound a lot like another way to describe a birthday. Still, they probably beat themselves up pretty hard over that one.

We understand that it’s difficult to talk to a stranger, finding the right words to try and hit things off with them. We suppose this cringy text is better than being a deplorable sleaze, but it just goes to the opposite extreme.

Something about speaking in such a stuffy manner generally doesn’t endear people to you. You should try to talk like you were born in the last hundred years, at least.

Honestly, “cringy” is a little too weak of a word to describe what’s going on here. It’s gross. Sickening. Outright appalling. We’re not sure what this person was thinking when they wrote all of this, but maybe they weren’t thinking at all.

At any rate, this is definitely the type of person you want to block as soon as possible. After all, it takes a special kind of sicko to think any of this was OK.

This guy came so close to actually being halfway respectable, but unfortunately, he decided to be cringy instead. Maybe he’s down bad and looking for love, but someone half your age and a minor? Have some standards, sir.

At least the teenager in this scenario was smart enough to respond properly. This strange man was obviously bad news, and anyone could see it.

Wanting someone to be invested in a relationship is totally understandable, but it doesn’t make any sense at all if the person isn’t actually in a relationship with you yet. This guy apparently didn’t get the message.

Why he feels so entitled is a mystery, but we are willing to bet this relationship ended up not working out for him. But hey, is anyone really surprised about that?

Admittedly, most of the cringe in this case is the guy just not knowing what he’s actually saying, but the implications he’s making are pretty cringy too. Nothing wrong with finding someone attractive, but attributing it directly to their ethnicity is kind of messed up.

Of course, there are certainly worse ways to start of a conversation, but this guy still didn’t do himself any favors. Presenting yourself as stupid rarely endears you to a stranger.

Most people like having some amount of attention paid to them from time to time, but there is definitely a way to be too cringy about it. Case in point, this guy right here. If someone isn’t answering this many texts in a row, it’s probably a sign that you should back off.

We’re not sure if his craving for attention actually ever went down, despite his claims. Maybe he should find someone who actually wants to talk to him?

This whole text exchange reeks of a young teenager, but the most cringy part definitely appears to be near the end. We’re not sure why “smirking like Satan” gets involved in this exchange at all, but it’s way out of left field.

Not to mention, what on Earth is the aesthetic “type” of person to like anime? This is definitely one of the people that give this entire group a bad reputation.

When someone gets too attached, it spells trouble. Well, calling this person attached might be a bit of an understatement. We’re not sure what their problem is, but they are definitely giving off some alarming cringy energy.

Rarely has that level of possessiveness ever worked out for anyone, so whoever is on the receiving end of this should get out while they can. For their own safety, if nothing else.

We get it: it’s very easy to get embarrassed after confessing to someone, only for things to not work out. But there are good ways to handle that kind of situation, and what we are seeing here is most certainly not it.

Why would you turn around and insult the person you had feelings for? Or, if this was actually a ploy just to embarrass someone, it didn’t work anyway, seeing as how the guy in question didn’t reciprocate those feelings. It’s just cringy all around.

Text roleplay with someone who didn’t agree to it is already cringy enough, but believe it or not, there are actually ways to make it even worse! You can decide to both describe all of your actions and stutter, in text. For some reason?

Maybe this person is just really committed to the bit, but they really shouldn’t be. We get the feeling that the recipient of this stuff would likely agree.

Toxic masculinity is something often attributed to men, as something they force on other men. But women can push this harmful narrative too. In fact, there are many women out there that will condemn men for doing normal things, like taking care of their skin.

What, like girls are the only ones who deserve smooth skin free of blemishes? That sounds like a pretty reasonable thing for anyone to want!

There are two types of people in the military: those who actually did something of value, but are humble about it, and those who likely did nothing important at all, and won’t shut up about it. This guy is most certainly the latter.

We’re just saying, it’s hard to admire or respect someone that is so adamant about you acknowledging their supposed sacrifices and commitments. Real heroes don’t feel the need to get praise from everyone.

There are many cringy things about this particular text exchange. First of all, it’s probably not a good idea to refer to someone as a “sweatpants princess”. Second, daring someone to kiss you is the act of a literal child.

There’s no denying that this guy was just incredibly desperate, but still, have some class. We know that’s a lot to ask, but still. The least you could do is try, right?

Being young means having a certain degree of carnal desire that’s a bit hard to suppress. But still, asking someone to send you naked pictures of themselves without even telling them who you are is a bit of a wild, cringy move.

And this is to say nothing about the awful attempt to play off this exchange by pretending to be intoxicated when it happened. Not to mention, this guy’s demeanor and speech patterns changed without explanation. Yeah, nice try buddy.

If your entire life was about to change, we couldn’t blame you for wanting to get a bit more physical fun with someone that you used to be with. Still, if your life is about to change because you are being arrested, that’s a big ask.

Maybe it’s not right to call this cringy per se, but it’s definitely a bit mind-boggling. Would it really be a good idea to sleep with someone right before they go to jail? Probably not.

There’s nothing wrong with being a fan. But it is kind of cringy to take it really seriously in a situation when it’s not called for. Very few people ever think it’s cool for you to drop your fandom on them so suddenly.

It’s worth noting that fandom is a strange thing: it’s very cool to the people who are in it, but almost always seen as cringy outside of that context. Unfortunately, that’s just how it is.

There are certain people that you just shouldn’t mess with. If you insult them, it’s practically guaranteed that you will not come out on top in most cases. The cringy part about it in this case is the inability to take the heat.

We’re just saying, don’t talk smack (and weak smack at that) to someone if you can’t handle a bit of reciprocation. That just makes you look even more pathetic than you already do.

Where to begin with this one? What is the cringiest thing about it? It might be this guy supposedly using the account of a dead friend to hit on someone else, but we struggle to call that something as weak as “cringy”.

Maybe it’s the “I’ve never seen you before but think you are gorgeous”. We probably don’t need to tell anyone why that doesn’t make any sense at all. Honestly, this entire thing is just cringy.

There are several ways you can blow an interview before it even starts, but trying to hit on the person giving you information on it is definitely one of the quickest ways to do so.

It’s more than just cringy, it’s unprofessional. And when you are trying to get a job, the last thing you want to do is come across as unprofessional, right? That just seems like common sense to us.

Building up the courage to confess to someone is difficult, for sure. When it doesn’t go well, that really sucks. But if it doesn’t go well, it’s always recommended to keep a cool head instead of getting super cringy. After all, that is a recipe for disaster.

At worst, the person you like is now weirded out by you. At best, you’ve still made a huge fool of yourself. Unfortunately, this person probably pulled off a little bit of both somehow.

One of the great things about texting is that you can break down communication to something nice and simple. We actually think it’s pretty desirable to have texting be so simple. Unfortunately, some people don’t feel the same way.

Honestly, having to input this many asterisks while texting sounds really tedious and annoying more than anything else. But hey, what do we know anyway?

The cringe here is obviously not intentional, which is nice. Unfortunately, whether or not it is intentional, it certainly isn’t comfortable, likely not for either individual. What is it with these people forgetting about deceased loved ones?

Hopefully this is the kind of mistake they only make once, but then again, the damage is already done. They probably could have afforded to apologize a bit more earnestly.

If you are on social media, there are probably a lot of people on your friend list that you haven’t actually talked to in a long time. If that is the case, you may be inclined to do some cleaning every once in awhile.

Unfortunately, someone might take this housekeeping a little too hard. Or should we say, way too far. Being this upset with someone for unfriending you on social media is pretty cringy, we don’t think anyone could really disagree with that.

We have to wonder if there are certain types of people more disposed towards writing out all of their actions and feelings. Maybe it’s the people who feel that their words aren’t enough? Unfortunately, this behavior often comes across as cringy.

We don’t want to be too mean to them, but seriously, they should probably try to work on using words to their advantage. Good dialogue gets plenty of things across.

What convinces someone that they should start roleplaying in the middle of a normal text conversation. Like, this seemed to be a pretty normal exchange, until this person made it cringy and weird.

It’s a bit odd to go from talking about a book to talking about massaging someone’s feet. It’s even stranger when the other person is quite clearly not into it. Wouldn’t you know if someone is down for that or not?

The cringe is strong with this one. It’s so strong, we don’t even know which part is worse. The way this person starts the conversation is already incredibly cringy, but when they get refused, their reaction is just as bad, if not worse.

You really don’t get to go on about how nobody likes you when you start of a conversation like this. Seriously, who does that?

Some memes are just cringy. Some are based, as long as you use them in the right place. This right here is a perfect example of how to use a meme in a cringy way, while completely ignoring how completely outdated this particular meme is to begin with.

Aside from that, going out of your way to make yourself sound sad and pathetic is rarely, if ever, a good move. Most people just don’t perceive that as admirable.

This text exchange is cringy in a different way: this time, it’s mostly just about one person being way too obvious with their poor attempts to scam someone. Besides, is this really the best way they could think of to try and get some pictures of someone?

Generally speaking, this kind of approach doesn’t work against anyone with two brain cells. After all, hacking like the kind mentioned here only exists in the movies.

Let’s ignore the text roleplay part of this because we’ve already harped a lot on that concept in this list. But even ignoring that, the person in this text exchange is just cringy overall. Like, they didn’t expect someone to ask who they were?

Moreover, is it really a good idea to get someone’s contact info from an acquaintance, then contact them out of the blue? That certainly seems like a bad idea.

Honestly, the weirdest thing about all of these text roleplay exchanges is the fact that people choose to narrate actions that aren’t very flattering. Why would you want to tell someone that you are hitting on that you are “sweating a lot?”

Like, do they believe that is actually helping their cause? That’s it’s actually increasing their odds? Maybe the problem with these exchanges is the misconception of what a good approach is.

The pickup line that was being used here was quite cringy, there’s no doubt about that. The fact that it was shot down by a terrible revelation doesn’t help matters at all. But the weird thing is, it’s almost admirable that this guy kept going with the bit.

Of course, “almost” is the operative word. You probably shouldn’t keep hitting on someone after they tell you that their father is deceased. They likely aren’t in the mood.

When you believe a message is automated, you may be inclined to provide a silly response instead of anything serious. That’s all well and good, except when it turns out that the message wasn’t automated at all.

But hey, at least this cringy response was presented to a therapist. Of all the people who could understand why you said that, it’s probably them. Of course, they might find some new things to talk about with you, all things considered.

What’s really the cringy part of this exchange? After all, the joke is hardly that good. In fact, it’s a really low-tier joke. But is it really that bad? Or is it the jealous boyfriend taking his girlfriend’s phone to try and combat the joker?

The joke may be bad, but the insecure boyfriend really appears to be the pathetic one in this case. Maybe both sides are a little cringy, in the end.

Everyone wants to be on the receiving end of some affection, but you shouldn’t try to get it from strangers with cringy lines and requests. Most people aren’t too interested in kissing some relative stranger or acquaintance just because it’s New Year’s.

This is far from the cringiest thing on this list, but it’s still just kind of painful to look at, isn’t it? Well, we suppose it could have been worse: this person could have requested some other troubling things.