From accidentally wrapping a boho skirt around a lady’s face, to being stuck in the middle of a divorce, people confess the most awkward situations theyve ever been in.
[Source can be found at the end of the article]
I was lab partners with a girl pretty far out of my league in high school chemistry. On the first day of class we had to go through the lab equipment with our partner to familiarize ourselves with the gear. I picked up the tongs and said to her, “these are thongs right?” without realizing my mistake.
As her face got redder and redder I just kept repeating “thongs, right?” over and over until someone else in the class said tongs.”
My sister left her husband for a man she met on the internet and ran away to Canada for two years. Her first husband had been part of the family since I was in junior high and had no close family left of his own, so we weren’t about to kick him out for something she had done. Fast forward to my sister and her new husband coming back to the States and coming to a family function where the ex was in attendance.
Which found me sitting on a couch between the ex-husband and the new husband while they discussed, of all things, various odd or interesting McDonald’s locations abroad.
It was so awkward as to be surreal.
In high school I went on a drama field trip to see a play. The theatre was one of those half circles with really steep seats and itty bitty walkways.
When we got to our row it was mostly full but the row behind it was empty. Rather than make everyone in our row stand up we had the brilliant idea to drop down into our seats from the row above.
Did I mention this was when those long boho skirts were in fashion?
Well, I swung my leg around the back of my seat and in the process wrapped my skirt around the head of the lady in the seat next to me.
I then had to spend the rest of the 3 hour play sitting next to the woman I had cocooned into my crotch.
I was crushing on this girl in my freshman health class in high school. I sat next to her, one day everybody is up and moving about for whatever reason, and I go stand next to her at this magazine rack at the back of the class. She asks me a question (I don’t remember what she asked), and I’m like awesome, she’s talking to me. So I start answering her question really in depth, really getting into it. Mid sentence, she cuts me off and asks me a completely different question which was (and I recall this perfectly despite this happening almost 20 years ago): “Do you get along with your parents?” So I was a bit startled, but okay whatever, I started talking about that like sudden conversation shifts were perfectly normal. Then out of left field she asks another completely different question. Here I finally paused… and looked at the magazines on the rack she was looking at and realized that she was reading article titles that were on the magazine covers out loud.
So I went and sat down and proceeded to never talk again.
My parents and their friends decided it would be so fun if their kids got married so they could be in-laws. So I was getting set up with their son. My mom’s friend literally went, “I heard you like guys who can play the piano! MY SON PLAYS THE PIANO! Let me get him to play the piano for you!”
She made him play the piano for me.
One of the parents went, “Come on, exchange numbers now!”
We awkwardly exchanged numbers while both sets of parents watched to make sure we saved each others’ numbers.
We were in our 20s.
Delivered a pizza once, the dad came to the door, was paying for it, when his teenage son (I’m assuming) came walking down the stairs. The son asks the dad, “Did you get a Coke?” The dad didn’t, and told the son “no.” The son started freaking out and cussing at his dad. The dad yelled back at him, threatening to ground him. So, the son attacked his dad, tackled him to the ground and the two of them are rolling around on the ground punching and yelling. I was pretty high at the time, just standing there quietly watching this go down. The dad had already paid me, so I just slid the pizzas out of the bag and left them in the doorway before walking back to my car. They were still fighting as I drove off.
So when I was 13, I had a friend who confessed to me that he was bisexual. Now I had no idea what that meant, but I figured Bi = 2, and therefore bisexual = had 2 sexes.
So I assumed he was like a hermaphrodite or something. And was therefore attracted to both genders because of that.
Anyways I just responded like “Oh, wow, really? That’s so weird.” and this misunderstanding probably continued for like 2 years when I asked him if he got periods and he looked at me like I was an idiot. And then died laughing when he found out what an idiot I actually was.
I had just finished fixing a lawn mower for this guy. We finish the deal and he puts his hand out to shake and turns out he has 3 fingers. Looked like it was from an injury rather than a deformity. I looked at it before I reluctantly and loosely shook his hand. I feel like I looked at it for way too long before shaking.
At my last job I was sitting up at the front desk while my coworker was at lunch. A student came up and wrote her question down — I ascertained that she was one of our deaf students so I wrote my answer to her question on the piece of paper and handed it back. We kept writing back and forth to each other, and then my coworker comes back. She starts talking to the girl and I was like, “oh she’s deaf” and my coworker says, “She’s not deaf… she just can’t speak.”
So I could’ve been speaking to her this entire time. I know I shouldn’t have felt like a jerk but I definitely felt like one. I felt my face turn super red, and oh man it was super awkward. I let my coworker take it from there and I hauled back to my office.
I can’t do mundane things like ordering at restaurants or getting takeouts because I’m a social kluts. I was so nervous my first time at subway for no reason really. I wanted the meatball marinara and didn’t think they would ask me for the types of food. They asked me what kind of bread I wanted, and I said French Toast instead of Italian herb….We kind of stared at each other for a couple seconds- until I repeated it again. I couldn’t sleep that day.
I worked at GNC for a couple of years (yeah, I know). Anyway, middle-aged gentlemen and seniors would often come in, putter around the virility section, and eventually ask for assistance with choosing a “test-testerone” product.
Totally fine. They were mostly insecure about having trouble waking up the guy downstairs. So I got used to assuring them that I talked to customers about the subject almost every day. And that I could offer a few products that would likely help.
One guy was so comforted by this information, he took it as an invitation to illustrate his troubles using his pointer finger as if it were his wang. He was saying things like “I can rub it, but won’t do anything” as he proceeded to jerk off his finger in front of me while I was alone in the store.
I was meeting my fiance’s extended family for the first time, it was some spring equinox shindig. I was sitting at the kitchen table with a bunch of ladies I didn’t really know, cousins, aunts, whatever. Well, this one lady walked in and she had this baby. This baby had these big, bulging, unblinking eyes. This baby looked totally freakish to be honest. Everyone was praising her baby, “Oh, she’s so cute!” “Oh she looks so alert.” One of the ladies was like, “Geez kid, you gotta blink!” Everyone laughed and looked at me as if they were wanting me to talk, and I thought I’d finally say something, and out of all the possible responses I could have chosen, I giggled and said, “Yeah, she must have some pretty moist eye balls.” They all stared and said nothing back and they didn’t talk to me for the rest of the party. I awkwardly left the table and hid behind my significant other for the rest of the party.
My neighbor and I both like woodworking. I am a younger single woman and he is an older man. I saw him outside and we were talking about woodworking, then his wife being out of town to visit her grand kids and my son starting school. As I was walking back inside my home I recalled I was gifted a lathe and hadn’t told him and he may want to use it someday, so I said…”hey if you ever need a lathe I have one.” he heard, “Hey, if you ever need a lay I have one.” And he promptly asked me if I just offered him a lay?! I was extremely flustered and said, “no, I am talking about woodworking, eehhh, wood turning….ummm playing with wood. no. TOOLS! I just got a new wood turning lathe tool.” He laughed uncomfortably, I went inside red faced and he’s been very nice to me ever since.
Back in college, I was helping my girlfriend move from her apartment to living back home with her parents. As the two of us were carrying her mattress upstairs, her mom said, “Didn’t you used to have a twin bed? Why did you get a queen? One person doesn’t need… Oh.
In college I came back to my hometown for holidays, and my girlfriend and a few of her friends decided to surprise me at a party another friend was throwing. We partied all night and made it home. In the morning my mom opened my door and screamed “Who is that in your bed?!”
Also once my dad walked in on us having sex. He did the whole ‘whoops’ thing and walked around the corner and goes “uh, you guys staying for dinner?” We didn’t, finished quick and then went out for dinner. The next night I sit down for supper with my family, and my mom goes “There better not be any kids running around here any time soon!
My husband is one of ten kids, good Catholic parents. One Christmas, when I had had a few too many festive wines, I got to talking to his mum about her pregnancies/ labours, etc. I made the astute observation that by baby number ten the labour was likely to have been similar to a small child shooting out the end of a waterslide. She was not impressed and I was mortified. My husband thought it was hysterical.
Summer I turned 17, my friend (who lives about 10 minutes walk away) turns up at my house saying she had locked herself out of her own house and needed help getting back in (long story short, she had dropped the keys through the letterbox before a driving lesson and forgotten that she wouldn’t be able to get back in until 5PM when her mother came home from work – her dog was stuck inside on a hot day with unknown levels of water, hence the panic and why she didn’t just hang out at mine for the next few hours).
We were in the middle of trying to hook the keys with a bent coat hanger when her boyfriend showed up and confessed that he had woken up that morning next to another one of his female friends and had no idea how he had gotten there, or what had happened. Cue a vicious argument right there in front of the house, me standing by awkwardly with the coat hanger still in my hand.
I quietly left and they probably didn’t even notice.
My ex’s divorced parents both attended her university graduation, her mom was staying with us, and her dad brought his new wife (incidentally, the woman he cheated on her mother with).
We all went out for a celebratory dinner afterwards…
It was AWKWARD.
My first year out of school, I was living in Chicago and all my family (and in-laws) were on the east coast. Thanksgiving rolls around and we’re not flying home. Instead, a neighbor (who we’ve become friendly with) invited us to Thanksgiving. She and her fianc are going to a friend’s for thanksgiving, and we’re welcome to join
So on thanksgiving day, we get in my neighbor’s car and drive for about an hour. Note that these are pre-Uber days. And as we’re driving, we learn that besides the friend, the friend’s parents (and one or two other people) will also be there. Cool — the more the merrier.
But we also learn that the friend has been diagnosed with terminal brain cancer and has a few months left to live at most.
You know how there’s five stages of grief? This friend spent Thanksgiving Day deeply in the anger phase. And I don’t blame her, but man was that awkward. We were stuck there for hours with a stranger who was thoroughly unthankful and extremely pissed off.
On the plus side, the pumpkin pie was delicious.
When I was in high school I had gotten suspended for pulling a prank on the school. I had managed to get our attendance office to update my parents contact phone number to my own so they wouldn’t know and I could get away with it. While they were trying to contact my “parents” I answered the phone acting as my father. Only to hear my father’s voice on the other end of the line. Turns out my school knew my fathers number the whole time and he was ready to pick me up in the office…
I was a nanny for a wealthy couple. I had just gotten back picking up the kids from their summer classes (one was in theatre, the other in an app designing workshop). Upon returning, the parents were already yelling/ bickering fighting.
The dad didn’t want to take the son to baseball while mom said something like “IT’S NOT YOUR PRACTICE TO MISS” … he stormed out with the boy, attempted to race out of the driveway and hit my car pretty bad as the wife and I watched.
He stormed back in, and they fought about divorce with me standing in the kitchen.
In second grade I wrote an erotic love letter to a girl in class. Erotic getting that I said I wanted to kiss her (scandalous).
I put it in her desk on our way to lunch. I felt accomplished.
As our class came back from lunch and recess, she found the note in her desk, and started reading it out loud for everyone to hear. I banged my head down on my desk in embarrassment. I don’t remember what happened after that.
Long story short, we ended up holding hands at the end of the year as part of a team building exercise. It definitely worked out in the end.
My mom’s last wedding was pretty cringe. It was just 4 people – mom and her new husband, his 96-year-old mother, and me. My choices of sleeping arrangement were A: sleeping in the same bed as this very very old lady who is essentially a stranger to me or B: sleeping in the room adjacent to my mom and her new husband’s room on their wedding night. So at the end I was like, “Wow! what a pretty night, I’m just going to check out this hammock over here…”
I work at a grocery store and was getting some lunch at the food service counter. The lady comes over and I am making small talk about how she is always alone in her department and it must be so hard to get everything done on her own. And then I said, and I quote It also doesn’t help that you have this idiot that doesnt do anything to help you, and she says who? him? and points over to the young man sitting in the cafe area on his phone. And I said yea, him!
Later found out that that young man was her son. The cringe was real.
My brother slept with a girl and for some strange reason he put the condom in his pocket after finishing. He forgot about it until he gave the pants to our grandma to wash and when she checked the pockets expecting to pull out some change of paper, she got something very different.
I was visiting my sister and her husband in England (I’m American). We hit the road and got a nice BnB in a small village in Wiltshire. It was cup season – Euro Cup, I think. England was playing. The BnB’s pub was packed with local villagers. My sister, her husband and I sat in a corner, quietly drinking our beers and watching the game on a small TV above the bar. I felt the need to urinate so I went to the toilet and did my business. I heard great yelling while I peed.
I walked back into the pub and it was quiet. All eyes were staring at me. I had no idea what I had done wrong. I had no idea what was going on. My sister waved me over to the table. I went to her and quietly asked what the problem was. Some fellow at the bar answered me in a loud voice: “You went for a slash during play, mate! Now we’re down one-nil!”
Apparently, in this village, going to the toilet during play is bad luck. I have no idea how these people hold back piss after three or four Stellas, but I guess they do. Either that, or they were just messing with the American’s head. To this day I’m still not sure. My sister and brother-in-law seemed to think they were earnestly angry at me. In the end, England won, so all was forgiven.
But that was some Children of the Corn stuff. ‘Awkward’ hardly describes it.
I was 14 years old, and my girlfriend and I (who I’m with to this day, I’m 22 now) were at her parents house when they were at work. This was a normal thing for us to do. So… being teenagers, things got a little steamy. Somehow we ended up naked in her mom’s bed. I get this weird feeling that her mom’s going to come home. I tell her about it, and she dismisses it.
And that’s when we hear the door open. We literally are butt naked just laying in bed. Nothing even sexual, because I had no idea what I was doing. My heart DROPS, so we scramble and get dressed fast. Her mom calls her name… her full name which is uncharacteristic. I throw my plaid shorts on and a DC shirt and blast out of the house, passing her mom on the way, jump on my broken down Huffy mountain bike and ride home. As I’m riding I feel a breeze through my shorts. I forgot my boxers, literally in her mom’s bed. They had hot dogs all over them and they said “Big dog.” That sucked. Funny thing now is we bought that house together, and have lived here for 2 years.
This was in 2016, I was 19, and it just became summer. Met this lady at the gym, a really good-looking 30-year-old. We go on a short trip to a trail the next day after making some plans, and go to her apartment for reasons.
Eventually an 8-year-old and a 10-year-old walk on when we’re on the living room couch, see me, and the older kid looks at his mom and yells “MOOOOOM!?”
Turns out they got out early from school. I felt really bad. Didn’t know she had kids…
She introduces me to them and we kick it off really good, eventually they’re showing me cool spiders like the brown recluse before I left.