Super Cringey Moments

July 6, 2023 | Sammy Tran

Super Cringey Moments

From failed high-fives to falling over in public, we’ve all experienced those moments that make us cringe years later. But fortunately, we’re not alone. These people took to Reddit to share their most hilarious and memorable awkward experiences. Just try not to face-palm too hard when you read this.

1. Wipeout

I was riding my bike into the school lot. I saw my crush. Is she waving at me? Better wave back. Waved back just as the chain slipped off my bike's gears. Two crushed balls and many frantic leg pumps later, I crashed.

(For the record: she was not waving at me).

super cringey moments

2. Let It Mous, Let It Mous….

I was at the store browsing some Christmas cards. There was a woman standing near me also looking at the display. I pick up one of the boxes of cards and look at it. She looks over and says, "That's a nice design".

I look it over and say, "Yeah, it is nice...It's too bad it's in French though. 'Mous?' What does that even mean?" She gives me the weirdest look and walks away. It wasn't until a few minutes later that it suddenly hit me. I realized I was holding it upside down and the card said, "Snow".

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3. Magic Phone

I was in line at the grocery store checkout and I noticed someone from high school was two people behind me out of the corner of my eye. I didn't want to engage in awkward conversation so I went to pull out my phone for a fake conversation but it dropped on the ground. I picked it up quickly and 'answered' it.

I was throwing out a lot of "yeahs" and "mmhmms" when the old high school friend tapped me on the shoulder with the battery from my phone in their hand and said, "I think you dropped this". It was clearly the battery for my phone and it was obvious I was not really having a conversation.

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4. Five-Second Rule

I was at this Mexican restaurant with my family one night. It was absolutely packed in there. Imagine downtown Beijing, but everyone is sitting at the smallest table possible. You can barely maneuver yourself to get to your table.

As we went to sit at our incredibly small table, I noticed that to the left of us was the cutest girl I had ever seen. She was adorable. Imagine Emma Watson crossed with Anne Hathaway. This was her. She was with a bunch of girlfriends, but no men in sight. Bingo I thought.

I promised myself I would try and strike up a conversation with her before the night ended (even though I was with my parents). Anyway, my family and I were sitting there, waiting for our food to come. That's when I notice said cute girl accidentally knocks her plate, and a potato falls to the ground, rolling over to me.

Not thinking, I did the dumbest thing imaginable. I picked up the dirty potato, blew on it to remove the dirt, and put it back on her plate. I still have no idea why I did this, but I did. She's just staring at me, while all her girlfriends are laughing like maniacs.

I excused myself and ran to the bathroom, balling my eyes out, and texted my brother to let me know when the girls had finished eating and left the restaurant. I was only 15. Worst night of my life.

The Worst Socially Awkward MomentsFreepik,freepik

5. Look On The Bright Side

This was years ago. I had just started working at my new job, which was located in a tiny strip mall. I made friends with the guy who worked a few stores down, and he'd stop by to chat to keep me company.

One day, he'd been complaining a lot, so I tried to cheer him up with, "Hey, it's not so bad. At least you don't have cancer or anything".

Guess who had cancer.

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6. Nice Save

I was in Venice. I was staying in a two-bed hostel with a girl from Argentina. I'm a guy from Canada. She was leaving early in the morning for her next destination. I was awake when she left. She went to give me a hug/two pecks on either cheek like a normal goodbye. I misread this gesture, and thought she was going in for a kiss.

I grabbed her, tried to make out, realized what was happening, and awkwardly let go. She just stared at me, eyes wide open with this horrified look on her face. My response: "Uh.... I'm actually gay". I tried to make it look like she was the one that made the situation awkward. Unsuccessful.

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7. I Really Must Dash

My wife and I moved into a new apartment. Shortly after we met one of the neighbors. He was a pretty nice guy, we exchanged basic personal details and both went about our business, but I never asked his name. Two days later, we saw him again. Only this time he didn't have the mustache he was sporting on our first meeting.

We talked to him again and had basically the exact same conversation as before. The next day, we saw him again, but the mustache was back! Now we start getting concerned. How the heck can this guy shave off his mustache, then grow a new one in two days? This went on for about a week.

Every other time we'd see him, he would have a mustache. Sometimes at different times during the same day! Was this dude wearing a fake mustache for half the week? Is he a private investigator wearing different disguises? Is he a crazy person, or does he just possess a Swanson-esque ability to regrow a full Flanders in the span of a few hours?

Finally I broke down and asked him about it. "Hey, how come sometimes I see you with a mustache, and sometimes it's gone?" He responded by staring at me for a few seconds then let me know that he lived there with his twin brother. It's been three years and things are still kind of awkward between us.

The Worst Socially Awkward MomentsWikimedia Commons

8. Candid Camera

I was walking around my house without clothes on after taking a shower. I walked into my boyfriend's computer room to try and find my bra and I decided to sit down at the computer and find a song on Youtube. Only, after about five minutes, I made a disturbing discovery.

I realized Skype was open...and he was in a video chat with someone who was sitting there, mouth agape, staring at my chest. I had to pretend I didn't know he was there and close my stuff out when it was done and walk away like nothing happened. I didn't want him knowing I knew he was watching me.

I see him ALL THE FREAKING TIME and all I can think is "he knows".

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9. Free Hugs

During my first week of college, I was walking down the path when some guy walking in the opposite direction let out a big "HEY!" and approached me with arms out for a big bear hug. Needless to say, I was horrified at the split-second decision I had to make, and as I stretched my arms out to return the hug I heard another "HEEEEY!" from behind me.

I turned around, still horrified, to find a very attractive girl about to return this random guy's hug. Being the bro he was, he offered a group hug, and I'm still friends with both him and the random gal two years later.

Moral of the story: awkwardness is circular. Make things even MORE awkward than before and you may come around the other end and seem like a reasonable person.

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10. You Shall Not Pass

I was walking to work one morning, very tired as it was really early. As I was walking along a narrow(ish) footpath I saw a woman with two small children with her, presumably going to school, walking towards me. They were taking up the whole sidewalk as they walked, I assumed one of them would fall behind to let me by. I assumed wrong.

When we reached each other, we sort of came to a standstill. Now, as I said, I was tired—my thought process was somewhat hazy and I was slightly annoyed they wouldn't move as there were three of them, so I decided to simply step over the young girl.

Now, either my legs are not as long as I thought, or the girl was deceptively tall, but I failed to get over her. Basically what I did was t-bag a small girl. I looked at the mother and she was horrified. I was speechless. I just didn't know what to do, so I just reached down, pushed the girl aside, put my head down and sort of walked/ran off.

The Worst Socially Awkward MomentsFreepik, prostooleh

11. A New Cultural Greeting?

A guy I'd just been introduced to as a friend of a friend tried to kiss me on the cheek as a greeting. I was obviously not expecting this and was in the process of putting out my hand for a handshake. Somehow my hand ended up jabbing him in the groin.

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12. Sixth Sense

In college, I took a class that had a blind girl in it. I am a pretty brisk walker and as I get up to the building to where my class is I see this blind girl approaching the doorway. I slow down my pace so as not to enter the door at the same time as her.

We are now in the stairwell and I am regretting not beating her to the door because she is going up pretty slow (which is totally understandable). I thought it would be awkward/rude to try and pass her on the narrow stairs so I am just kinda hanging out behind her. Boy was I wrong!

We are alone and halfway up one of the flights she stops climbing. The moment she stops I freeze mid-step like a little fawn. She then slowly turns around and looks directly at me. Being me I just stare back at her with my mouth slightly open. She then slightly tilts her head as if she is honing in all of her other senses to try and locate me.

We are just standing there, me mid-step and crouching like a cat burglar and she looking directly at me, for about 10 seconds. She then says, "Hello...?" My stomach drops, but at this point, I feel as if I have put too much effort into being undetected so I remain completely silent.

The look on her face tells me that she is not completely satisfied by my response. After a few more seconds of silence, she turns back around and continues walking up the stairs, and I continue to stand as motionless as a statue until she goes through the door out of the stairwell. I still can't shower the creepiness off of me.

I spent the rest of the quarter tip-toeing around like the ground was covered with spiders whenever I was close to her.

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13. Ringo Who?

I was selling merchandise at a concert for a pretty well-known band. A guy came up and was looking at the CDs. I asked if he wanted to buy one, and he replied, "Thanks, but when we recorded it we were given a bunch of free copies". He was the drummer.

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14. Slo-Mo High Five

This is my cousin's story, but it's the funniest and most awkward thing I've heard. He worked in a large supermarket for a long while, and got to know the customers pretty well. Anyway, one guy comes in (regular) and they chat while he rings up the shopping.

As the customer leaves he holds up his hand to say bye, but in that sort of 'stiff wave' when it looks like you're holding your hand up for a high five. My cousin thinks he's high-fiving, so goes in to high five. The trouble is, halfway through this maneuver he realizes his terrible social faux pas- the dude is just waving. But that's not the worst part.

The problem is, he just keeps going, albeit slower, and while maintaining constant eye contact. Instead of just owning it and doing a high five, he gently presses his hand on the customer's, like a slow caress, and then removes it. Awkwardness ensues.

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15. He Really Blew It

I ran into this super awkward guy I used to work with on the street the other day. It was one of those, "Oh I see him from far away eyes down EYES DOWN DO NOT MAKE EYE CONTACT!!" moments...Anyway, he saw me and stopped me to say hi.

I didn't really have anything to say because I didn't really know the guy, plus he has terrible English so all he says is "Yes yes yes" while nodding his head. Then as I wrap up this already super awkward encounter I go to shake his hand and he holds his hand up but it is CLUTCHING A TISSUE.

Before I know it I am shaking his closed hand with a tissue in it.


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16. Pinball Wizard

In grade eight science class, I have a new laptop given to me by the school because my handwriting is awful, but that's another story. I'm in the special ed class, and have been in it since grade five so I don't exactly have many friends because kids are mean like that.

We do some work in class, finish, and the teacher tells us we can chat for the rest of the class. So I run up Windows 3D pinball (the greatest game ever) and start going away at it. After a few minutes, I notice the room is oddly silent and look over my shoulder.

Literally every kid in class has stopped talking and is crowding around me and watching me play. I'm obviously going all bug-eyed, wondering what is with all this attention and why they don't all just ignore me like they normally do.

They keep staring for a time and I don't know what came over me. But I shout out in this really weird voice that was totally unintentional (will try to use punctuation to make it read like it sounded because it is really key) "Yaaaayyyyeee...III'm POPPPPuuuularrrrrrrrr".

Everyone laughed for a bit until someone shouted back, "No you're not," and people apparently agreed and left me alone.

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17. Drowsy Dog

I'll never forget the most awkward moment in school. I was in the US and had just moved from Argentina. My English was pretty good, but a lot of "slang" and stuff was still unfamiliar to me.

This one girl shows up to class 10 minutes late and had obviously been crying, so the whole class is silent, the teacher asks her what's wrong. And she responds, "Sorry, we had to put my dog to sleep, he was my best friend, I'm so sad and miserable"...The whole class is silent at this point. Then I messed up BAD.

I BURST out laughing and say, "That's so stupid, why did it have to be put to sleep? WHY WOULD YOU EVEN CRY ABOUT THAT AM I RIGHT?" At that point, she bursts out crying miserably and everyone is looking at me like I'm the worst person in the world, and I'm just like, "What??"

The teacher starts yelling at me to leave the classroom, I'm bright red out of embarrassment and confusion as to what happened. Later, after school, the teacher demands to talk to me for being so insensitive, I tell her that I didn't understand why she was so sad, the dog was just going to wake up later.

The teacher then understood my confusion, I never made the connection that putting to sleep meant euthanization. I LOVE dogs so I suddenly understood her pain, I was soo embarrassed that I never apologized to her. I still feel like a tool about it.

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18. The Pleasure Is Mine

So I was on a date going out to dinner at a nice-ish restaurant. The waiter comes up and introduces himself and I, for some reason, think this is a situation that calls for a formal introduction. I stand up, introduce myself, and go for the handshake. He is obviously confused. I realize this and sit down as he reaches for my hand.

Then we shake while I'm half sitting. He serves us for the rest of the night and not only am I embarrassed, my date is embarrassed on my behalf.

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19. The Thick Of It

This is the story of the most awkward situation I've ever been in.

I stayed the night at my girlfriend's house, the plan being we would help her mother move some furniture around before her house got valued, then we would head to my house (my parents were away) and I would cook her dinner, then we would play videogames. So was the plan.

Now, my girlfriend's mother is a little unpredictable at the best of times, and in this situation, she was under a lot of financial and work-related stress, so she was being very snappy. Anyway, we got up fairly early and helped move some stuff around, it was all pretty tense but we managed. That is, until we had to move the big wardrobe down a flight of stairs and out the door.

Anyone who has ever moved house knows that couches and wardrobes were made by the devil to ruin relationships, and this was no exception. Halfway down the stairs, chao ensued. My girlfriend and her mother got into a screaming match about something, which evolved into an argument about how my girlfriend is never around to "help out," and spent too much time with me.

Things got enormously out of hand, and they were just screaming at each other about me and how I'm a distraction and how she spends too much time with me, all whilst I am stuck behind a wardrobe pinned between the two screaming people.

We eventually got to the bottom of the staircase and the screaming intensified until I thought there was going to be an actual physical fight. I had no idea what to do. I wanted more than anything to defend my girlfriend, but I knew if I intervened, I would just make everything worse, since the fight was about me.

So I just stood there awkwardly, which is not something I'm proud of, but I don't know what I would have done differently. Anyway, the argument got to the point where she actually kicked us both out onto the street, me without my phone or wallet, and my girlfriend in her pajamas, incredibly distraught.

We were left with no choice but to walk three or four miles to a friend's house, then take the 40-minute train trip to my house. We are still together and she lives with her mom again, who's a little more stable now. We laugh awkwardly about the situation.

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20. Turn The Other Cheek

I met this guy at a mutual friend's party. He asked for my number so we could meet up while he was still in town, and I agreed to hang out with him while making it clear it would be casual and just getting to know each other as friends. Not a date.

It's the end of the night and we're on the same subway headed back to our respective places. His stop is a few ahead of mine, so we say our goodbyes as the train approaches his stop. He leans in to kiss me on the lips but I strategically give him my cheek.

He looks sad and confused, so I lean in to kiss him on the cheek to put him out of his misery and send him on his way. He thinks I'm leaning in to kiss his lips, so we do that awkward dance til I finally get his cheek. (Keep in mind that we're on a packed NYC subway and this is all taking place in the time the doors have opened for a stop).

He gets off the train, pauses on the platform for a moment, and then marches straight back into the subway car in my direction to try kissing me on the lips one more time. I awkwardly give him my cheek again. He gets back off the subway and the doors close. I cringe and shake it off and the subway car emerges into a slow clap.

I am a socially awkward penguin every day, everywhere.

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21. Just Walk Away

I just "coincidentally" ended up in the same place as this cute boy I'd seen on the bus a few times. Seriously, we made some eye contact a few times on a bus trip, and I thought he was cute, so I timed my trip home from the gym today, hoping to run into him again.

Feeling that I was on the right side of the line between confident and creepy, I got off at the same stop as him (totally opposite direction I needed) and walked up to him making some excuse about needing directions. I asked him his name, and where he was headed. It was the most awkward conversation I've ever had.

I was nervous as heck, and he looked terrified of me. I did realize once we started talking that he was a lot younger than I thought, but when he told me he was in the 11th grade I almost died of embarrassment. Being ridiculously awkward myself, and totally out of my element hitting on guys, I still asked him if he wanted to hang out sometime.

He took a few minutes to answer, and was finally like, "I don't think I can". I was like "Ok! But this is the direction I need?" and walked away. To clarify, I'm in my mid-twenties. I do kind of wish I had played it cool at the end, like "take my number in case you change your mind," but I totally just pointed randomly and walked away.

I'm not really very smooth. Today it's a little easier to laugh about it.

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22. A Formal Rejection

I was in a friend's room and he was trying to get me to ask a guy in our dorm to a formal. Now his roommate was distracted on the computer and tuned in only when my friend gestured vaguely toward the door (where his roommate happened to be sitting at his desk) and said, "Just ask him already".

Roommate: "Ask what?"

Me: "To the formal this weekend".

Roommate: "Sure I'd love to go with you!"

Me (smiling for some bizarre reason): "Oh no, not you!"

Cue awkward silence. Bonus: his family was visiting and walked in before anyone had said anything else.

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23. One Down, One More To Go

When I was small, I was always thrust together with my two cousins who were born the same year as I was. I'm a guy, they were both girls, and we never seemed to have anything in common; they were close, and seemed to resent my presence.

Once, when all of our families were gathered at my aunt's house, I walked into the room where they were talking and overheard one of them say something about strawberry shortcake. We usually had strawberry shortcake for dessert there, so I assumed that's what they were talking about and said, "Oh, I love strawberry shortcake," in an attempt to enter the conversation.

They turned and gaped at me, and one sneered, "YOU like Strawberry Shortcake? YOU'RE a BOY". They ran off laughing, and I was left with the horrible realization that I had apparently just confessed my love for a pink doll thing.

One of my cousins died a couple of years ago, and while I miss her, (we got along better later on) I still occasionally reflect that one witness to my shame is now gone. Watch your step, cousin Jamie.

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24. Say It, Don’t Spray It

Sitting at Subway with some friends enjoying a nice sub. My side of the booth faces the door. A girl from school walks in and as I go to acknowledge her with a badass head nod, I also decide to take a drink. As I am sipping, my head nod begins.

My lips are no longer in contact with the straw and the upward flow of lemonade and iced tea make a nice fountain that sprays all over my face and shirt. She quickly looks away and tries to hide her smile. My friends do not. Made fun of to this day…

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25. Iced Out

At pretty much any large group gathering I'm forced to attend (the worst are for work), everyone's usually standing in groups of 2-5, chatting away. I look around quickly for someone who's either super chatty or someone I can actually think of something to say to. I walk up to the group—but it all goes wrong. 

I realize at the last minute I have no angle to properly insert myself into the group. I end up standing slightly behind someone who can't see me, who continues chatting away. Other people try to focus on the conversation but clearly see me loitering creepily. 5-30 seconds pass.

Anxiety rises, and I bail. I head to the next group. I repeat this humiliating loop until I finally get too flustered and make a break to the bathroom to regroup. EVERY SINGLE TIME.

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26. Face Plant

Band practice in 7th grade was right before lunch, so by the time class was over, I was starving. Also, the band room was so far away from the lunch room that we always ended up last in line.

So, on this particular day, I walked quickly (too cool to run of course) to put away my trombone the second class ended, and proceeded to nonchalantly jam my hands in my jean pockets and walk briskly out the door. That was my intent, anyway.

Unfortunately, there were two steps up before you exited through the door and I caught my foot on one of them. Keep in mind, this was the late 80s, the era of very tight jeans, so I was unable to retrieve my hands out of my pockets and face-planted.

I then lay there face down, hands still jammed in my pockets, as the entire band class walked over me in their rush to lunch.

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27. Instant Own

I was walking to school with my cousin who is new to our school, and he starts asking me if I'm popular there. I said, "Yeah man, I have tons of friends". Right at that moment, a girl walked past me—and did me so dirty.

She said, "No you don't".

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28. Sigma Self-Own

I was taking the metro home from uni one day when, as I was about to leave the station, I feel a tap on my shoulder. I turned around and there was an attractive girl standing there. So she says to me something along the lines of, "I just wanted to tell you that you're really cute and I like your style".

Without thinking or missing a beat I replied, "I'm sorry, but I think you're confusing me with someone else". She gave me a 'what the eff' look for about a full minute after that while I glanced around nervously hoping the conversation was over.

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29. No, Thank You

I was once on a bus, going to town to buy some WoW playing time (yes, I bought the cards as I was too paranoid to pay for it online), and as the bus was packed the only seat happened to be next to me. Some time into the journey, a bunch of teenage girls got on and stood near me, one of them sat next to me and the bus went on...

They were chatting away as teenage girls do and I was looking out of the window dreaming of being back home stroking my cat and other manly activities when they decided to get off. This girl put her hand down to help herself get off the seat and instead of putting her hand on the seat, put it right in my crotch and went bright red and apologized while her friends laughed.

I said, "No, thank you," as a terribly bad joke and they all gave me this kind of sad pitiful look and got off.

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30. Panic Mode

In ninth grade, about 12 years ago, I was going through the tail end of puberty—awkward as heck. But I blame my sister for my most embarrassing moment of all. I was talking to this cute girl that I had a huge crush on when my younger sister walks up and says, "Oh, so THIS is the girl you like?"

Looking back on it, it was probably nothing to get too worried about, but at the time I was so embarrassed that I started having a panic attack, my vision started closing in and I began hyperventilating. Good times.

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31. Brace Yourself

The most memorable awkward event for me happened in undergrad a few years ago. I was on my way into the Natural Sciences building on campus to turn in a lab report and was still in a large "turtle shell" back brace from a car accident a few weeks before, and was mostly concealed except for a metal bar that extended from the top of my stomach to my collar bone.

A very attractive gentleman was holding the door open for me, bridge style, and being quite short I smiled and moved to enter the room with my body facing the door. However, I was prevented entry when my metal bar became hooked on the door handle and I was stuck for a few very long seconds as the man holding the door waited for me to move.

I could not, and had to have him help me unhook myself from the door. He didn't say a word.

The Worst Socially Awkward MomentsFreepik,freepik

32. Delayed Reaction

Usually, if I am walking around campus, my mind is elsewhere. If someone, even someone I know well, passes by and says hi, I'm usually startled at first because I wasn't paying attention. Then I try to speak, but my voice is too slow to catch up, so I just raise my eyebrows and voicelessly mouth "Hi" but to everyone it probably looks like I'm just gaping at them.

Sometimes they look like they wanted to have a conversation, but since I don't actually respond they usually walk on. Once they are gone, I regain the ability to speak. Sometimes I mumble to myself what I should have said. Then someone else walks by and thinks I'm insane.

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33. Double Double

I was at Tim Hortons last week and spotted a really handsome saxophone player I used to hang out with. Eager to greet him, I ended up waving with both hands. It was an idiotic move—and I ended up dropping the two iced caps I was holding.

They hit the floor, I looked down, and looked back up to see him staring at me like I was seriously challenged. I ended up buying two more.

The Worst Socially Awkward MomentsFreepik, freepik

34. Let Off Some Steam

Blech. I was standing in line to pay for my food at the Cafeteria in the dining hall in College, and for some strange reason, I felt the need to release some kind of energy. So I made an involuntary noise. The problem is I was looking around and accidentally made eye contact with the guy right next to me and audibly went "MEEEEH" at the exact moment of eye contact.

I immediately looked down and tried to contain my laughter, paid, and ran away.

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35. World’s Best Wingman

I was at a friend's house in high school, and he invited two girls over. We started drinking, and watching YouTube videos and listening to music, and all of that. After a few drinks, my friend began making out with one of the girls, and I just sat there watching them. The other chick was texting on her cell phone.

My friend looks back and sees me not making out so he picks up the other girl and puts her on my lap. Then we sat there for a good 30 minutes watching my friend make out. After I got bored of watching them making out, I asked the girl sitting on my lap to get off, and I went to browse GameFAQs until they finished.

I'm now out of college, working as a software developer around a bunch of other guys, and still haven't kissed a girl. In my daily life, I will see maybe one woman a week, and they're usually 15-20 years older than me. I haven't talked to a chick my own age since high school.

Is that awkward enough?

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36. Less Is Moe

So I go to Moe's (a fast food tex-mex restaurant that is common in the south) a lot. I go at least four times a week. Well, there was this one girl that worked there who was pretty cute. Coincidentally, she also worked at my Dad's office. I had seen her around the office a few times and I guess she knew who I was.

So one day I am in Moes and I am checking out, and she randomly comes up to me and says, "Hey, aren't you Dr Derp's son?" Being ridiculously awkward, I absolutely freaked out because this girl was talking to me.

Well, in an attempt to respond, I said a sentence completely backward. I didn't reverse the words themselves, but the order of the words were backward. So clearly this girl was kind of confused and just gave me this weird look and I immediately just went "Uhh yeah" and left.

It was incredibly embarrassing and helped me realize that I have zero game. A few months later, I saw her again at my dad's office and I don't think that she remembered it because it wasn't nearly as awkward as I thought it would be. Yep.

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37. Say The Magic Word

Just yesterday I stepped out of the office to go get some lunch. Mentally I was 100% absorbed in what I was working on. I walked into this Mediterranean place called Roti and walked up to the counter.

Me: "Could I get the (food)?"

Lady (jokingly): "No".

Anyone else would have immediately identified the joke, but I just stood there completely dumbfounded with a blank expression on my face. No? That's not the expected response. How do I respond to this situation? Should I say "please?" Eventually, she said "just kidding" and asked me the specifics of my order...

It was all very weird and awkward.

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38. Great Icebreaker

I went to a debut (which is a girl's 18th birthday. It's kind of a big thing here) and I mistook the girl's uncle for a waiter, so I asked him for ice. Since I was a close friend, I was sharing the table with some other friends and the girl's family. Her dad spent the entire night making fun of the uncle and my friends kept laughing at me.

In my defense, he was wearing a very similar outfit to the waiters and was kinda just standing there like one. Still really awkward though.

The Worst Socially Awkward MomentsPexels

39. Russian Away

I was with a good friend of mine and she asked if we could drop by an internet cafe to say hi to a buddy of hers. We get there, and he's giving off mega creepy vibes and I tell her in Russian (as we both speak it), "Babe, let's go. This guy's creepy". She proceeds to laugh—and my stomach sinks.

She explains that he's also Russian and. heard. everything.

The Worst Socially Awkward MomentsPexels

40. Chain Reaction

Ah, high school, an emotional bucket of awkwardness.

I was in my first year in this school, so I didn't know a lot of people outside of my class yet. However, I noticed that among those two years older than me, there was a group of people who had all the signs of power/heavy metal enthusiasts (the leather jackets, chains, spikes, hoodies etc).

Being younger and a socially awkward penguin, I decided that it would be inappropriate if I just approached them and said hi. So I decided that I SHOULD IMPRESS THEM! I had just purchased one of the longest pocket chains I could find and thought that it would be cool to come down the stairs facing the metal group's usual gathering bench, sporting my dark clothes and awesome long chain.

However, as I start walking, the super awesome long chain gets caught in а strap, hanging from my boot. I trip and fall all the way down in a bundle of muffled squeals, textbooks, and chain, stopping pretty much at the feet of said group. Never before have I wished for the ground to swallow me up more.

The Worst Socially Awkward MomentsFlickr, dualdflipflop

41. None Of Your Business

We have an IT guy that comes in once a week. As the resident IT girl, he comes over to catch up with me on the issues before he sets to work. We're chatting and he asks me if everything is okay with my eye. Apparently, it was twitching. Anyway, I say it's fine because I honestly don't notice anything.

Four hours later, it's closing time and I walk over to his desk to say goodbye. He says, "If your eye keeps twitching like that people are going to think you're winking at me and start talking!"

In general, I'm a pretty witty person, but given that it came out of this IT guy who wears sweater vests and seems really shy, I was taken aback. Instead of saying something clever, I blurt out the unthinkable. I go, "Uhhhh everyone's business is the business of the everyone knows what the business is of the people's business is the we all know"...

I think I was trying to say "You're right! Around here everyone knows everybody's business," but that didn't quite happen. He just sort of sat there looking stunned and I shuffled away absolutely mortified.

The Worst Socially Awkward MomentsPexels

42. Howdy, Neighbour

I was trying to be sociable and say hello to my neighbors while they were outside. The conversation went something like this.

Me: Hey how are you?

Them: We're fine, you?

Me: I'm great, how are you?

The Worst Socially Awkward MomentsShutterstock

43. Sir, This Is A Wendy’s

I ordered a meal at a Wendy's drive-thru. After they were done taking my order they said, "Thanks". For some reason, I replied with, "Drive-thru please".

Got some awkward stares at the window.

The Worst Socially Awkward MomentsShutterstock

44. How Do You Like Them Apples?

I have quite a few embarrassing moments to speak of but one in particular that happened recently at work...

I work at a movie theater, so sometimes I have to be the ticket taker which is my least favorite job. You basically stand in one spot for eight hours tearing tickets. I'm incredibly antsy and can't stand still for more than 30 seconds, so I'm constantly walking back and forth and whatnot. Kind of irrelevant, but whatever.

Anyhow, a girl who I work with and I have casual conversations randomly throughout the day when she happens to walk past me (she's ushering). Towards the end of her shift, she walks by again and stops and we chat again. I thought she smelled nice, so I said, "Hey your hair smells like apples".

She just stared at me and walked away slowly. She didn't speak to me for the rest of the day either. I didn't notice how creepy I sounded until afterward.

The Worst Socially Awkward MomentsShutterstock

45. Wrong Wave

I always wave at people that are waving at the person behind me. You'd think I would have learned by now to check behind me before doing so.

The Worst Socially Awkward MomentsPexels

46. The Awkward Dance

Every single day I have at least one encounter where I'm walking toward someone and we do that little dance "Oh, I'll go left...right...left...JUST GO!"

The Worst Socially Awkward MomentsPexels

47. Microwave Maverick

My most awkward moment happened while I was taking my lunch break at work. I went down into the kitchen to warm up my soup in the microwave. I must have been super distracted that day because I paid no mind to the one other person in the kitchen who happened to be standing right beside the microwave I was about to use.

I grabbed the microwave door handle and opened it, not realizing it had actually been in use. The guy standing there was warming up his lunch burrito and it wasn't done. At that point I figured, screw it. I've committed. I took his lunch out and handed it to him, and stuck my soup in there.

And he just gave me a blank look and walked away with his half-frozen burrito in hand.

The Worst Socially Awkward MomentsPexels

48. Just Saying Hi

I was recently dumped after a two-year relationship and so me and a friend decided to hit a local bar to see if we could...try our luck? Anyway, I get a few drinks in me and tell my friend (in a very It's Always Sunny In Philadelphia way), "Just pick out any girl in this bar, and I will speak to them...preferably attractive".

So he picks out this hot chick who is sitting with her friend and like some muppet I walk towards her. Then suddenly a bartender walks toward them to pick up empty I think "It's alright I'll wait till he's gone". Then I decide it'll also be good if I wait for her friend to go away to the bathroom or something to reduce the awkwardness…

I spent 20 minutes staring at them. They didn't notice but eventually, I just said "Screw it" so I went to speak to this girl and I said, "Hey I'm _____ I saw you across the bar and I thought I'd come on down and say hi!" She just stared at me with wide eyes, laughed, and said, "Hi".

For the next five minutes, I sort of just stood there before saying, "Wellp! Great to meet you, I'm going over there now".

The Worst Socially Awkward MomentsPexels

49. You Have To Hand It To Him

I was working at a small hardware store a few years ago. I saw someone in the aisle and approached them from the side and asked "Hello sir, do you need a hand?" BIG MISTAKE. He turned around, and I could see he was missing an arm on his other side. Of course, I completely froze. Thankfully, he was cool about it.

He just looked at me, paused, and said, "ba dum tssssss". At some point, he also made a joke about not having any tricks up his sleeve.

The Worst Socially Awkward MomentsShutterstock

50. Too Sexy For My Car

I was taking my driver’s license test in an older Jeep that I had just bought and the driving instructor was an awkward larger guy who didn't talk much. Once we had been going for a little bit in awkward silence and he tried to talk and all he said was, "Looking in good shape".

I, for some reason, thought he meant me. NOPE. I replied just as awkwardly, "Thanks I guess I do hit the gym pretty often". To which he said, "Not you, the car". We didn't try any more small talk after that.

The Worst Socially Awkward MomentsShutterstock

Sources: Reddit,

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