55 Most Cringe-Worthy Moments Shared On The Internet

By Uplift Post

August 12th, 2021

From oversensitive responses to messages meant to be private, we’ve found some of the most cringe-worthy moments on the Internet.

It’s clear from these 55 photos, texts, and posts that people either need to chill WAY out or be much more aware of their situations.

See if you can read these without feeling downright embarrassed for humanity.

1. Long time no see

Wow, that’s next level awkward. How close can you be to someone if you don’t know they died?

2. Stop, ok, I’m sorry

This guy absolutely got that response that was coming to him. It’s actually kind of nice to see someone back off immediately. Maybe that’ll teach him a lesson.

3. That’s gonna be a table for 1

Just a hunch, but we don’t think this is a good way to invite people to spend time with you. We also don’t think this self-professed “good guy” gets what it really means to be a good guy.

4. Just throw out your phone

Is it just us or do you wonder how old a person is if they “got boobs” over the last 4 years and some creeper is already pointing that out over text?

5. I remember now

Nice to add that final touch at the end. And yes, Adrie, you do sound weird.

6. King of the friend zone

No wonder shorter men tend to be angrier. When you carry someone around on your shoulders all night only to have them make out with another guy, you know you’ve been friend-zoned.

7. It’s a no from me, dawg

Wow, poor Sean really poured his heart out before getting a pretty cold rejection. We cringe for you, man!

8. Is that clear?

This person sounds like a real treat to date. It’s a total mystery as to why they’re still single.

9. Oops, I guess your face just looks like that

When you think someone has used the Faceswap tool but really that’s just their face. We’re guessing the Washingtons Capitals’ social media manager got in trouble for this post.

10. How not to break up with people

Well, if you have to break up with multiple people at the same time, maybe it is efficient to do it all at once. But then your screen cap ends up on Reddit.

11. It’s a virgin

You gotta love a kid that doesn’t know that the word virgin also applies to cocktails. Seriously, Nick, clean up your thoughts!

12. Presidential shove

Ok, putting politics aside, this is the most upvoted photo on the whole /cringepics subreddit for good reason. Let’s all agree we’d be cringing over ANY president shovings aside world leaders to take center stage. Don’t think it’s that bad? Here’s the video. Make sure you watch until he fixes his jacket. Yikes.

13. Then “you are” kind of a jerk

Since when did contractions become a tool of the lazy and ignorant? This is the height of taking yourself too seriously!

14. Please let this be fake

Is it too much to hope that it was a clueless assistant who posted this to Mia Farrow’s Twitter account? If you look closely under the time, you can see that the search term used to find a photo of her own daughter was “Mia Farrow and her black children.” I mean, don’t you just have a photo on your phone somewhere?

15. Yes, you struck out

Taking a hint seems to be a lost skill. We don’t blame this deliverywoman for listing him as “Creeper” on her phone. Just let a woman do her job and get on with her day!

16. At least the dog can’t be offended

Guess someone needed to do a bit more research before they shared their advice to groom this dog.

17. In a relationship with no one

Facebook should definitely keep around the rule that both people have to agree they’re in a relationship together before one person can post about it. Otherwise, you end up with creepy and cringe-worthy moments like this!

18. Unrequited love

Professing love over Facebook to someone you really don’t know is a special kind of clueless.

19. Creepy story, bro

No, just no. If you want to roleplay in a message, at least make sure you have a willing participant.

20. Try not to post crimes online

At least it makes a nice screencap to send to the police for solicitation.

21. Poor Rhianna

Can’t a girl take a vacation from the paparazzi in peace? Can you imagine trying to relax on a beach only to find this crowd behind you?

22. Rhianna truly can’t catch a break

Ok, we get that celebrities make lots of money off of their faces, but does that really give people the right to get up close and snap a pic when they’re just trying to live their lives? The worst part is this guy still posted this photo instead of feeling creepy about it!

23. The Internet is not your therapist

Not sure how many willing sperm donors she’s going to get with this tactic.

24. Christmas fetus

It’s one thing to be happy for your family when they’re welcoming a baby into the world, but it’s quite another to find a way to print out an enlarged version on the sonogram and put a Santa hat on it. That’s next-level cringe-worthy.

25. Not in the cute way

Wow, well if you ever wanted an honest review of how a date went, you can just put yourself in this woman’s shoes and walk right back on that wish.

26. Posers gonna pose

When you’re trying to look like a sensitive soul with a penchant for writing ballads to your online audience but then someone mentions you’re holding the guitar upside down, you should feel seriously embarrassed!

27. We’re gonna guess the answer is “not yet”

Wow, that’s cold. A loving message from mom or passive-aggressive rejection of the truth?

28. Yes, you’re scary

We can’t believe this guy is for real. But we think we know why women are scared away, and it’s not because of his “intellect.”

29. It’s all about me

Someone really is so vain (or perhaps insecure in this case), she thinks every Facebook post is about her.

30. We can’t be friends

This goes beyond “take a hint” to “take a strongly worded instruction to leave someone alone.” Why do people think this kind of persistence would win over anyone?

31. Keep your hands to yourself

We don’t care if you’re a man of God, there’s no need to get handsy. This was truly a cringe-worthy moment at Aretha Franklin’s funeral.

32. Not yay

Read between the lines, people.

33. You want beef?

There’s a big difference between a stranger asking if you “want beef” and your grandma offering to make you dinner. Reddit thinks this post might be fake and, honestly, we hope it is.

34. That’s the difference between people who don’t know what they’re talking about and everyone else

Don’t criticize anyone unless you truly know what you’re talking about. We just hope this moment gave Adam some perspective about what he posts online.

35. You’re still the worst

Ok, he might have been the worst boyfriend in the moment, but we think the alleged murderer might be the worst person, objectively speaking.

36. Have fun!

Some people take cluelessness to a whole new level.

37. Someone needs to learn politeness

We don’t think the recipient of this creepy, unsolicited message is the one who needs a lesson in politeness. Seriously, why do so many people think this is a good way to start a relationship?!

38. Wasn’t it a compliment?

Damned if you do, damned if you don’t when it comes to taking a compliment from this guy.

39. Guess he should have worried

Well, that’s awkward. Then again, that’s what happens when you friend everyone you’ve ever known on Facebook.

40. Smooth move

Gotta love when politicians try to act cool. It’s not really working out for Theresa May here. We’re loving the looks on everyone else’s faces though!