16+ Moments That Win The Award For Most Embarrassing

We all have things that we look back on and cringe at uncontrollably, don't we? I mean, I can barely look at old photos of me without wanting to die. However, some people are confident enough to upload their horrific moments of regret to the internet!

So, please enjoy these 16+ pics so embarrassing they made us feel better about ourselves!

"My mom told me not to blink during my 2nd grade class picture."

Reddit | ntaylor7746

I hope she was impressed with your strong efforts to not blink! I know that if I'd have done this, my mum would still be teasing me for it now!

"My junior year yearbook picture."

Reddit | gamerskaterchef

There's a lot going on here really, isn't there. Also, whoever cut that arrow in their hair didn't even do it straight, so I'm assuming this kid did it to themselves?

"Titanic and iceberg ⏤ Halloween 1998."

Reddit | mrspetie

I feel like the girl on the left, the one dressed up like the Titanic in case you missed it, has the facial expression of everyone who looks at this picture.

"My son was trying to make a 'web shooting' hand. I’m proud and ashamed."

Reddit | joelwinstead

That guy in the spiderman costume looks completely out of his depth here. That suit is also incredibly tight.

"At 14 I was dating a girl from another school. I surprised her on her birthday by dressing as a clown and busting into her class singing 'Happy Birthday'."

Reddit | 1doublezero

They went on to say, " She was mortified! When the dust settled she thankfully realized the thoughtfulness that went into the gesture." I would have never spoken to them again.

"A friend of mine called a restaurant about a spelling mistake on their sign. And they changed it."

Reddit | enis_with_a_p

"Apparently there is a spelling mistake here?"


"Just put an "o" somewhere, anywhere. Take a guess."

"8th grade me thought I was cool as hell, went like this to a Christian concert event."

Reddit | mastermoto7321

I mean, you had me sold on the Christian rock concert alone, but the hair and the cargo shorts really complete the effect!

"My mom told my dad he better not embarrass her at Grandma's this year. He showed up to Christmas dinner dressed like this."

Reddit | ketchuppacket

The stain on the pants is a really good touch. However, I don't think I'd have been able to sit there like that for the whole meal. I mean, after the joke passes, are you supposed to have serious conversations like that?

"Mom you are embarrassing me!"

Reddit | notyouravrgd

The whole scene seems to be a bit much for the girl sitting down, as it has apparently reduced her to tears. Either that or the mother poked her in the eye with her pink balloon.

"Had my 6 year old son's drawing tattooed. Four months later he confesses his friend, Kevin, drew it. Sometimes ignorance is bliss."

Reddit | helicopterwindow

I mean, it's pretty good to have for a funny story. However, I can't say I'd want it on my body forever.

"Some days you just wake up and think of your biggest mistake."

Reddit | Crono464

This is something of a classic nowadays. However, it never ceases to amaze me. I mean, how did they not think this would come back to haunt them?

"I don't understand how this mistake was even made."

Reddit | samjs45

Again, I'm embarrassed by how long it took me to notice what was wrong. I guess he just thought it was a touch screen? Actually, that still doesn't make sense!

"We decided to embarrass our daughter at the airport after 3 months away (we don't normally dress this way)!"

Reddit | ron1337

What I particularly like about this one, is that they felt like they had to specify that they don't normally dress like that when they posted the picture!

"I may have made a mistake choosing this college..."

Reddit | sometimesdragonscry

"And if you look over here, you'll see all of our accomplishments!"

"But, there's nothing here...?"

"Let's move on!"

"Grade 8 graduation. I wanted to look like Ludacris so I got cornrows. Narrator: She did not look even remotely close to Ludacris."

Reddit | islandfool

Look, I'm not going to have a go here. I spent a lot of my teen years with very striking curtains as I wanted to be like Jack White.

"Easy mistake to make..."

Reddit | tomthumb1979

The main question that I have about this whole thing is... Who the hell throws away a full burrito? Savages, that's who!

"I made a huge mistake this morning."

Reddit | pickles_on_reddit

Anyone who would leave these two things next to each other in the first place deserves this kind of thing to happen to them, frankly!

"Me at 17 (2010) living it up in Vegas."

Reddit | pelirojo67

Surprisingly, the person in the picture went on to explain that the choice of attire did in fact not help them to get any action as they so desired.

"My mom dressed me like this so I was easy to spot when she picked me up..."

Reddit | pluckems

Oh boy. I mean, that will definitely make you easier to spot! At least they look happy here because something tells me they won't be looking back.

"This is how you dress when you’re 12 and tap dancing to Sk8r Boi at your recital."

Reddit | mariguana

Either the perspective is slightly off here or this kid had crazy long legs! The person who posted this said that they have since grown to be over 6 feet tall, which makes sense!

"My boyfriend's 10th grade picture is pure rebellion. According to him, his mom cried when she received the pictures back."

Reddit | krdearman

Ooft, that is a powerful statement they were making right there. Also, their hair looks like it is made of Lego.

"Our dog died and the neighbour's kid made us a card. She was embarrassed by it so she scratched her name out and wrote her mom's name instead."

Reddit | jaykayak

Thankfully, the person who posted this said that the card was so daft that it actually really cheered them up!

An Uncomfortable Misunderstanding...

Reddit | PyroNecrophile

The person who posted this explained, "I got my 80 yr old father this as a gag gift. When he opened it, he got embarrassed and immediately tucked it away. Later, I privately asked him why he got all weird about it, and I found out that he was under the impression that it was a sex toy."

"Never be ashamed for your love of tuna!"


Tuna is one of the greatest foods available, so never try and hide your love for tuna, as tuna loves you as much as you love it.

"My mother got embarrassed when she 'found my girlfriends panties' on our kitchen table."

Reddit | TommyNoble21

It would have been even more uncomfortable if this person had put it on and started wearing it before their mother figured out what it was.

"I was in an early 2000's transitional phase between awkward and total embarrassment."

Reddit | PigSlug

I just cannot fathom what the point of this look is. I mean, it's magnificent and all, but just...why?

"I'm ashamed of how many times I tried to grab that fry."

Reddit | Slamdance

I've got to be honest, I couldn't see what the problem with it was for an embarrassing amount of time, so I'm in no position to judge.

"My friend once thanked me for hosting her at my 'Humble of Ode' and I never plan on letting her live it down. Had this made for her new apartment."

Reddit | ARL381

I'm suddenly reminded of the time I sent "dong dong dong" instead of "ding ding ding" to a group chat I was in, and they still haven't let me forget it. This is torture for your friend.

"A different walk of shame."

Reddit | boogyman12

You know they've got a storm waiting for them at home. I salute you, soldier, and wish you luck.

"I was drunk in the background of a photo once and my friends constantly remind me of it. This is my pillow and sheet of body tattoos."

Reddit | emmamcisaac

It's because of stories like this that I act like I'm allergic to cameras. No one will ever catch me in a moment of weakness.

"Woke up to my dog barking. She was stuck and too embarrassed to look me in the eye."

Reddit | IamBoss

He got lost in the sauce there, getting a bit too comfortable on that couch until he realized he couldn't un-comfy himself. It's alright, bud, nothing wrong with asking for help.

"You can almost feel the shame."

Reddit | kiplarson

Roomba, you had one job to do and you did the complete opposite. I hope you feel shame. All you did was make more work for yourself.

A Moment Of Reflection.

Reddit | LucidGoose

I know we're kind of beyond pet-shaming now, but at least this one looks like it worked. The gears are turning in his mind, "That was foolish of me. How dare I let that mouse take advantage of my dinner. Never again."

"Shame overtook him."

Reddit | Malfaisance

Maybe he's just trying to impress the girl who took the photo. He sees her using the pen a lot, she must like it, maybe if he looks like the pen then she'll like him too!

"Not sure if public shaming of his children, or if he wanted to dress like this in the first place."

Reddit | mikelp82

I really hope his kids got the message because he destroyed a pair of pants and a jacket for this.

"My gf's mom bought these for her and she couldn't figure out why we both agreed they couldn't be worn in public."

Reddit | MrNastyHempire

Not only is the acronym unfortunate, but these are really pushing it with what are considered "shorts."

"So, my office is having an awkward group photo contest. How'd we do?"

Reddit | pansyass

You did excellent. I could see this as a cheesy promo image for a new prime time office sitcom show. That's a good way to rep your workplace, I think.

"Mother-in-law bought these to embarrass me. It didn't work."

Reddit | t0pd4wg

This is the pinnacle of strength. Being able to take what was meant to shame you, what was meant to stay hidden, and flaunting it to the world. Besides, that's a killer onesie.

"Awkward wardrobe malfunction."

Reddit | toddhenderson

How...did this even happen? I don't think you'll be getting any good selfies from that angle.

A Lookalike You Don't Want.

Reddit | tr_morrison

Well, 20,000 crimes might have been solved, but it seems one got away, so make that 19,999.

"My girlfriend's way of protecting her uggs."

Reddit | trizzzyt

I understand wanting to protect your shoes, but if you go to these lengths, maybe they're not worth wearing at all.

"Trying to explain to the 70 year old Swiss man who offered to take our pic that his finger was covering the lens."

Reddit | Inesmu

At least this is a holiday picture that has a funny story behind it, not like every other holiday photo I've ever had to look at!

"I had a reservation for a table of one. I call it the table of shame."

Reddit | TrumpetGal401

Oh, come on, you didn't have to make them face the wall like that. They probably feel bad enough eating by themselves. This surely won't help.

"My friend's GF's dad sent them an xxxxl cutting board for their housewarming by mistake."

Reddit | gwackr

How do you even make this mistake? Also, why the hell is anyone making these things in the first place? Who has onions that big?!