These Awkward Moments Take “Uncomfortable” To The Next Level

Are you really human if you don’t end up in a brutally awkward situation at least, I don’t know, once a month? We’ve all been there, and the memories are enough to make our skin crawl. But, at least you can feel good about one thing: You probably haven’t experienced an awkward situation as bad as the ones you’re about to read!

1. Lap Dog

I once worked at a wedding reception and watched as the bride got intoxicated and sat on some other dude’s lap for two full hours, flirting with him while the groom sat there by himself at the head table with a defeated look on his face. I could not have felt worse for this guy. I have no idea what happened to this couple, but I can’t imagine they lasted too long.


2. Well, I Guess That’s One Way to Travel…

First physical of my life. I drop my pants and the doctor says turn your head and cough. For some odd reason that I cannot quite understand, I thought he said turn your head and crawl. I cannot explain the levels of confusion and awkwardness that followed when I started to nonchalantly crawl around on the floor of his office…


3. Meeting the Family

My cousin used to have a crush on me. She was two years younger than me and she saw something in a movie where the girl surprises the guy by waiting and lying naked in his bed. When I was 20, I was coming home where I live with my grandmother. My cousin came to my grandma’s house and waited on my bed wearing only her underwear and nothing on the top. Pretty bad right? No—this story is so much worse.

My grandmother failed to mention to her that I was bringing my college girlfriend for the weekend. As I was unloading the car, my grandmother offered to show my girlfriend to the room where she was going to be sleeping. But when they opened the door, they found my cousin who started screaming profusely.


4. By Any Other Name

I asked a co-worker what his son’s name was, and he answered Legolas. After two seconds of laughing, I realized he wasn’t laughing. His son is actually named Legolas.


5. All in the Family

I once went to my girlfriend’s for Christmas in high school because my parents went on vacation. During dinner, her sister decides to announce she’s pregnant. She’s a 20-year-old single college student. But that’s not the worst part. Who’s the dad? My 27-year-old cousin. They had met at one of our family functions.


6. Taking the Fall

So, I work in a cnc workshop, and we often engrave stuff. This particular guy wanted a nice wooden jewelry box for their wedding anniversary with a custom message he emailed me. For some reason, he chose to give the box to his wife at the workshop. Obviously, this is not the most romantic place I can think of but whatever.

The guy’s wife starts to look confused and tear up: “you don’t remember the date?” Guy turns pale, looks at me, says: “no, I’m sure it’s a mistake.” Me: “no, I’ve copied it straight, can’t be wrooon…waaait a minute, omg, it’s my fault, I’m so sorry, I will redo it right away, no need to pay, please accept it as a gift…”

Wife gets angry a bit at me, but they leave with a different box and the correct date. Guy comes back next day and pays triple the original price without a word.


7. Good Grief

My mother and I were out walking and we came across an older couple we knew from the local church. Their eldest son had passed the previous year from an inoperable brain tumor, and their younger son just moved out for university. Mum starts with, “Must be nice to have the house to yourself! More time for Church!”

The conversation devolves from there. She ignores all hints to drop the subject, including the mother stating they hadn’t been back to the church since their son passed. The couple were obviously horrified. I couldn’t end the convo quick enough. Afterward, my mother told me I was just being immature and had no conception of what “polite adult conversation” was like.


8. This One Holds Some Weight

The last time I was at my doctor’s office, I was kept waiting in the exam room for a really long time. Like long enough to go through all three magazines in the room. Eventually, severe boredom set in and I started looking for other things to do to pass the time. There was a scale in the corner of the room, so I thought, “What the heck? Let’s weigh some stuff!”

I started with my shoes, and eventually moved on to the magazines and my clothes. When I ran out of personal stuff, I surveyed the room and decided that I would like to know how much a chair weighed. So, I picked up the doctor’s huge chair and placed it on the scale to investigate. This was the exact moment when the doctor and her resident decided to enter the room. There I am, wearing nothing but a hospital gown and socks, balancing a chair on a scale for no apparent reason…

At least I was able to satisfy my curiosity!


9. You’ve Got a Friend in Me

I knew a couple who invited all of their Facebook friends to their wedding. They were expecting about 700 people to show up, and they prepared the banquet hall accordingly. In the end, less than a hundred showed up. I guess they learned the hard way that not all of their Facebook “friends” were actually their friends in real life. Awkward!


10. The Real Accident

I made the mistake of moving over the holidays last year. I was emptying out my bedside dresser of clothes and whatnot. My top drawer had two large open boxes of rubbers inside. I stuffed ribbons of protection into my pockets and left. Lo and behold, I’m involved in a major car accident on my way to the new house.

One short ambulance ride later, I’m in a private Emergency Room with just a nurse, my girlfriend, and myself. My girlfriend had to remove my pants. But first, she had to remove everything from the pockets. So there she is, glaring at me as she pulls more than thirty ribbons of rubbers out of my pocket in front of the nurse. I swear, it looked like a magic trick. They just wouldn’t stop coming out…


11. A Crazy Story

When I was seven years old, my doctor told me to drop my pants. It was for the good ‘ole hernia check, but at the time I had no idea what that was. Not knowing any better, I ran out of the exam room and screamed to my mom that the doctor was crazy and wanted to see my private area. I specifically remember screaming, “Mom, get your coat! This guy is crazy!”


12. Speaking from the Heart

The most cringeworthy thing that I have ever seen at a wedding was not the fault of the bride or groom, but of the bride’s father. I was the best man at this wedding, so I had a front-row seat for the entire thing. The couple was marrying young after the bride had fallen pregnant. It obviously wasn’t planned, but they clearly loved each other and it was the right thing for them to do in their eyes.

Anyway, come the wedding day, I’m sitting next to the bride’s father at the reception and I can see he’s looking at his prepared speech repeatedly. I can see phrases like “not ideal,” “would’ve preferred not to welcome you into the family under these circumstances,” etc. Just before the groom gets up to give a speech, the bride’s father excuses himself to use the washroom, leaving his “speech” behind.

I knew that something needed to be done before he turned the entire wedding into a nightmare. I’m not ashamed to say that I swiped the speech and then pleaded ignorance when he returned and asked what had happened to it. In the end, he stood up and muttered a few generic words about love and then sat down without any issues. I never told the groom, and I’m happy to say that they’re still happily married twenty years later.


13. Special Day

I was eating at a restaurant and heard the hostess ask a couple she was seating if they were out for anything special. The husband replied, “No, it’s just our anniversary.” It has inspired my father-in-law to drop that line almost any time he goes out to eat now.


14. Marking His Territory

Way back in high school, my then-boyfriend was over visiting at my house. I decided to be nice and heat up some leftovers for him from the fridge. Right as I set down the plate, my dad walks in and says, “That is our food.” He takes the plate away from him and sits down to eat it at the opposite end of the table. I just stood there in painfully awkward silence until my dad finished and left.


15. Hardheaded

I still cringe when I think about my first solo date back in high school. I had a huge crush on this girl, thought she was really cool and I loved her art and I couldn’t believe she said yes. We went to the zoo because it was free and we were just broke teenagers and we had a blast. Afterward, we went to grab some food at this place before having to split off to go home.

Our trains were heading in the opposite directions and the entrances were across the street from each other, so I walked with her to her side to say goodbye. I closed my eyes and awkwardly leaned in to give her a kiss goodbye, and she went in more for a hug. I ended up headbutting her in the face and her nose started bleeding.

I was so embarrassed and didn’t know what to say, so I just asked, “Are you okay?” She replied, “I think so.” Still not knowing what to do I just said, “Okay, bye!” and then ran across the street to catch my train.


16. Let’s Call a Square a Square

About a year into our marriage, my wife and I bought a dining table and chairs. It was our first “real” furniture! My wife was so happy, she posted pictures on Facebook and wanted her mom to look. Well, her mom commented on the phone that it was a nice “oval table.” Wife is immediately upset. “You didn’t look,” she says. “Yes I did!” her mom insists.

“It’s not oval, it’s rectangular.” “No, it’s an oval, I looked.” Wife finally gets her mom to actually go look for real. Her mom sees that she is incorrect. But it gets even worse. She creates this gem: “Well that’s what I call it!” “Um, you call rectangles ovals?” This has become a running gag for us. Whenever we lose an argument, we always end it with, “Well, that’s what I call it!”


17. Shock and Awe

I went to the hospital when I was a teenager and my doctor was a rather attractive young lady. She had to check me for testicular cancer. The room was curtained off and my parents were waiting right on the other side, fully within earshot. The doctor was looking away when I pulled my pants down and she said, “Oh my gosh,” in an annoyed voice when she turned to find me pantsless.

I thought I had done something wrong and said sorry. As it turned out, the removal of my pants hadn’t been what had annoyed her. It was that her beeper had gone off. I guess she had been extremely busy. Now, the story isn’t too embarrassing at face value, until you realize that my parents could hear but not see this short exchange.

I don’t want to imagine what they thought had just caused a pubescent teenager to have to apologize to an attractive doctor while she was examining his privates…


18. Are You Negging Me?

On a very awkward date, the guy asked me: “So, at what age did you start wearing tampons?”


19. A Scheduling Conflict

I once witnessed a bride show up almost two hours late to her own wedding. This was in Southern California, in an open field with no water and no shade. She shows up and wants to get married in her yoga outfit. The groom got very angry and shut the whole thing down. When she refused to change her clothes, the groom decided to just leave her there looking stupid and they never got married.

I spoke with my uncle and it turns out that the groom had been having some suspicions that his fiancé was sleeping with her personal trainer. When she showed up to the wedding in her yoga outfit, it was all he needed to see to call off the wedding. She ended up getting married to her personal trainer shortly after, and then they got divorced soon after.


20. Pregnant Pause

I need to learn to shut my mouth when I’m at the hospital. I saw a largely pregnant woman and made a stupid comment about “Bet you can’t wait to get that out of you!” She said “Eh, not really. The baby doesn’t have a heartbeat and I’m just waiting to have the stillbirth.”


21. This One Takes the Cake

I once attended a classmate’s wedding. They were both young, maybe about 22 or 23 years old. There is apparently a “caking” tradition in some parts of the country where, when they cut the wedding cake, the couple feeds each other a little bit of it and smears some onto each other’s faces as a joke. The bride had absolutely made it 1000% clear to the groom that she did NOT want to be caked.

He did it anyway. And not just a small smear. He full-on smushed the entire slice into her face. She was stunned initially, then got up, with her face full of cake, and yelled “YOU JERK! I TOLD YOU NOT TO DO THAT!” She then ran as fast as she could to a back area near the reception. The groom tried to follow her, but the bridesmaids and the mother of the bride stopped him.

So, the groom ended up sitting awkwardly at the head table by himself while half the wedding party rushed off with the bride. She stayed back there for like an hour. They eventually did let him go back there to check on her. We could hear her crying and them arguing. The rest of the reception came to a screeching halt until one of the bride’s aunts emerged and directed the servers to clear the tables and put on some music.

They got divorced two years later.


22. I’m Just the Driver

Once when I was 17-18, I drove a co-worker home after our shifts ended. I pulled up to her house to see her mom outside and looking up at the balcony…where my co-worker’s stepfather starts throwing entire closets of clothes out and onto a parked car. I would have assumed she would jump out and quickly say thanks for the ride to try to defuse the situation. Nope.

Instead, she stood next to my car, with the door open, essentially trapping me while she watched her parents’ screaming match ensue. I was there for 15 minutes until the authorities arrived and she finally let me go.


23. Crushing Defeat

I finally got the chance to talk to my crush—and I blew it so hard. After a long silence, our conversation started with me saying, “So…haha, how do you start a conversation with someone?” Then she was like, “We’re talking right now, aren’t we?” That wasn’t even the worst part. I didn’t know what to say and after a minute of more silence, I just walked away.


24. But Tell Us What You Really Think!

A friend of mine was in medical school. As part of his program, he was working in the local clinic one day. While there, he went in to see a patient who needed a breast examination done. Now, keep in mind that this was a middle-aged but very attractive patient. While performing the exam, he accidentally said: “Hmmm, yes, very excellent….uh I mean normal! Very normal.” He was beet red the rest of the day…


25. Dancing on My Own

I was talking to a friend of mine about our upcoming prom. She said that she couldn’t wait to go and that she had just bought the most beautiful dress. I was a bit confused because I didn’t know she was going and asked her who was bringing her. She said our mutual friend John. Now, this is where it gets really awkward.

I knew John had actually asked another girl we knew; I’d seen him ask. So I say to her, “Are you sure? I thought he was bringing X?” She looks at me with a confused expression and gets out her phone to text John. We then stand in awkward silence for what seems like an eternity until finally John replies, BUT TO MY PHONE.

He asks me to tell her he isn’t going. I show her the text and she just says “Oh…” then looks at me and says, “I have to get back to my mom” and practically runs away, holding back tears. As it turns out, John asked our friend, then decided he didn’t want to bring her anymore and just asked X instead, all without ever telling her!

I have never felt so awkward than when I was having that conversation, and have never been so furious at someone as I was at John.


26. Look at Where You Came From

I was looking at my mom’s phone cause she wanted to show me some pictures from what she did that weekend. I swiped one too many times and came across one of her…ahem…”adult” pics. I felt my soul jolt out of my body seeing that stuff.


27. Audible and Deadly

I tried to release a silent toot near an empty aisle in a supermarket. It was not silent. And I wasn’t alone…


28. Sister Act

At a wedding I once attended, the groom gave a speech thanking everyone for coming. Somehow, the speech devolved in the space of about two minutes into a straight-up roast of his new brother-in-law. They were friends, and the brother-in-law seemed to take it in good humor, but there’s only so much implication of “I’m for sure going to be sleeping with your sister tonight” that you can take before it becomes really cringy.

It didn’t help that, first of all, I barely knew anyone there because I was a plus one and, second of all, I was at a table with the elderly relatives from that side of the family, who were less than amused, to say the least.


29. Paging Dr. House

I was with a friend of mine and her sister in their truck. For whatever reason, we were talking about Harry Potter characters. I said “What’s the name of the werewolf professor? Professor Lupus?” I was wrong, it’s Lupin. Lupus, however, is the disease that killed their mother.


30. The Conclusive Clap

I had an awkward “will they won’t they thing” with this lady for like two years. She was an awkward and shy type of girl in that really endearing way. I was into her but never realized she was into me so I never made a move. She was shy and never made a move. We both were in and out of relationships over this period also, we were never single at the same time so there was never any momentum to get together.

It was just one of those things, you’re into someone, nothing comes of it, you move on. She lived with a friend of mine at the time in a house share. One night I was drinking with my mate watching movies and she decided to join us, which happened occasionally, only this time she was single and I’d recently—literally a week earlier—become single.

Two years of pent-up-emotion-why-has-this-not-happened-before relations happened that night. Next morning, while still in her bedroom, I got the worst phone call of my life. My ex called me to advise she had chlamydia and I should go get tested to be safe. Naturally, I was obliged to pass on that message and completely crush this poor girl in doing so. It still makes me cringe a decade later.


31. This Isn’t the BBQ You’re Looking for

I invited a friend over for a BBQ. He didn’t know anyone and has never been to my house but seemed really eager to go. So, I was a little irritated that he was almost two hours late. I was just about to text him when I happened to look over my neighbor’s fence. What I saw made me burst out laughing. See, the neighbor was also having a BBQ…

It was like it happened in slow motion. I saw my friend in the neighbor’s yard chatting up some old lady. Our eyes locked. I saw the realization literally hit his face. I still laugh about it. I swear the guy turned white!


32. Blowin’ in the Wind

When I was giving birth to my second child, I was determined to not have a bowel movement. I even took an enema to help prevent this from happening. It did clean me out as intended, however, it also caused the worst gas that I had ever had in my life. I had an epidural, so I couldn’t really feel anything. By the time I was ready to push, I figured the gas had already passed.

I let the doctor know I was ready and he went right down there “in the danger zone.” He timed my contractions and let me know when it was time for a good push. I pushed with all my baby delivering might and inadvertently ripped the biggest, longest gas I have ever heard. Right in his face. I saw his hair literally blow back. The fact that he was young and attractive didn’t exactly make me feel any better about it…


33. She Took Notes

My ex wife later came out as a lesbian, and we divorced. Years later, I went to her wedding, where she married her now wife—who was my ex-girlfriend.


34. Pure Fantasy

It was in my junior year of high school and I was invited by a friend to attend a local dance at an all-girls school nearby. I had nothing else to do that Friday night and I figured nothing bad could happen. Yup, I was wrong about that one. During the night, this girl globbed onto me, as my friends like to say. She was not in the least bit attractive, rather rotund in nature.

She obviously was very into me, and I, the socially awkward penguin that I am, decided to try to talk to her outside instead. I figured if I got to know her a bit better maybe I’d somehow find some attraction. I didn’t want to be a guy who would write her off immediately because I believe every person has some type of beauty to them.

As an average guy, I’m not exactly a lady’s man, so I figured as a beggar, I couldn’t be a chooser. We exchange numbers. I figure if I’m not attracted to her, I can find a new friendship of some sort. She asks to hang out and I make it a double-date sort of deal with a friend of mine who had met a girl at the dance as well.

I realized here that me and this girl had nothing in common and that her physical appearance was simply too much for me to deal with. I gave it a shot, and I wasn’t interested. So, I didn’t make an effort to ask her out again. She, however, was waiting for me to ask her out as she thought everything was going great.

Eventually, I had to tell her I wasn’t interested because her friends were telling me to ask her out. I called her and said I wasn’t interested. This is where the tale takes a dark turn. She then goes and tells her friends that she’s going to “cut my balls off,” among various other colorful phrases. Then, a few weeks later, through some casual observance on Facebook, my friend discovered that this girl had written stories about me on her Fanfiction website profile.

He said I “had to read them for myself.” I did—and they’re burned into my brain forever. It turns out they were about me doing EXTREMELY graphic things with another man. We’re talking about descriptions of bodily fluids and my attack at the hands of another guy. In these stories, I found out that my body did things I didn’t think were possible. We discover she also had a thing for Harry Potter fanfiction, including stories about Remus and Sirius going at it while transformed.

She scared me away from dealing with girls until college and here I am.


35. Too Late Now

The first time I took a bus in a new city, I pulled the stop request cord at the wrong stop. Instead of just being a normal person and telling the driver that I didn’t mean to do that, I got off the bus and walked for an hour in the rain.


36. Call the Fire Brigade

This one girl in high school faked a seizure because I told her that I already had a girlfriend. The gym teacher called 9-1-1 and when the paramedics got there she just got up and ran off. I guess she got in some pretty big trouble for doing that.


37. It’s the Little Things

I scored an interview for a dream job. I did all of my research about the company, bought a new suit, the whole shebang. I gave the man interviewing me a firm handshake, answered all of his questions easily, and felt pretty confident. After finishing the otherwise flawless interview, we shook hands again, and I said, “Thank you sir.” To my horror, she replied: “It’s Ma’am.”


38. Worse Than a Toothache

When I was studying to become a dentist, I was shadowing a doctor in the Emergency Room for a couple of weekends as part of my education in general medicine. Well, late one Saturday, a young girl, around 18 years of age I think, comes in with her parents because of the severe stomach pains that she was experiencing.

The doctor asks a few questions and then asks the girl to take off her pants and lay down on her side. The doctor then puts on a glove and shoves a finger up the girl’s butt. I had seen this before, standard procedure, but never with a cute girl as the receiver. So I was already feeling a bit embarrassed by that point.

But it soon got so much worse. While this is going on, the girl’s father turns to me and asks me how many years I’ve got left until I’m a doctor. My response was, “Well umm, I’m actually studying to become a dentist.” He gave me the most awkward look I have ever received in my life, clearly wondering why I was even there to begin with. Really made me feel I was at the wrong end of things…


39. Bad Timing

My best friend in high school was in the process of being grounded and having his phone taken away. As he was handing over his phone to his mom, he got a text from me that said “Hey, I found your mom’s bedroom toy” accompanied with a picture of a medieval battering ram. He told me that they both saw it right as the transaction was taking place, then held each other’s gaze silently for what he described as an eternity.


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40. Tonight’s Gonna Be a Cringey Night

I was a banquet manager at a hotel for years, and have worked hundreds of weddings. The worst one by far was the time the bride was at least twenty years younger than the groom. It was almost definitely an arranged marriage. Only about twenty people were invited to the reception, and the only decoration was a lousy quality massive blown-up picture of the bride and groom in the shape of a heart.

When the bride and groom walked into the room, someone put the Black Eyed Peas’ “Tonight’s Going to be a Good Night” on over a CD player. Then the song played again, and again, and again for three hours straight. The only time it stopped was when the CD ended, because apparently no one had learned how to use the repeat feature. So, they had just burned a CD with the same song on it twenty times in a row. When it did stop though, someone just got up and restarted it.

Also, there was no drinking at this event.


41. I Don’t See Color

I worked security at an aquatic theme park and was watching Jeopardy in the employee entrance. One of the veterinarians came through and watched it with me for a bit. He said he watches it religiously and he’d passed the test for the show and was hoping to get selected. He’d heard that they like to have a diverse group of contestants, and they hadn’t had a black guy for a while, so he liked his chances.

A few days later, there are two black contestants, so when I see him leaving the next time I say, “Hey, did you catch Jeopardy last week?” “No, why?” he responds. “There were two black guys on it,” I explain. He just stares at me blankly for a few seconds, and walks off. That’s when I realized it was a different gentleman than I had the previous conversation with.


42. Wordless Exchange

I got paired with the uber-hot cheerleader for a chemistry project. I started tapping my pencil against the top of the desk due to nerves and, somehow, it flew out of my hand eraser first then ricocheted into her eye. She had to go to the nurse and hated my guts all without me saying a single word.


43. I Have an Announcement to Make

One time, I was getting a checkup at the doctor’s office. I went to the bathroom and peed in the cup, put it on the little counter thing they had, went back into the room, and waited for a very long time until the doctor finally showed up like thirty minutes later. She told me “You have protein in your urine.” I immediately blurted out, “Probably because I slept with someone last night!”

Unsure of why I had said that and visibly confused, she awkwardly replied, “I’ll mark that down in your chart. Congratulations!” She was trying hard not to laugh. I felt like a complete idiot. But, in the moment, I had legitimately assumed that this fact might somehow make a difference in the results of my urine tests.


44. A Man of the World

I used to videotape weddings, so I’ve seen it all. This one couple from New Jersey was the spitting image of two characters from the show Jersey Shore. They were super into appearances and very over-the-top gaudy. During their church ceremony, they had their very awkward 60-year-old uncle put on a culturally-appropriated costume, stand up, and chant around the church, giving what I can only assume was some kind of blessing.

It was so weird, inappropriate, and out of place. I assume they wanted to seem “deep” during their ceremony. They mixed some multicolored sand together in a vase, too!


45. Wish I Were You, Kiddo

Wedding photographer here. Easily my most awkward moment was at one of my wedding. The father of the groom, apparently entirely sober this whole time, gave a ten-minute toast that devolved into openly complaining that his son got to sleep with the bride and he didn’t. But that was just the beginning of the nightmare. 

This wasn’t a mistimed joke about how pretty she was, this was a full-on lament about growing old and how women didn’t find him attractive anymore and that all he wanted was to take his daughter-in-law to bed. I got a few photos of the bride and groom reacting in horror to this and then I went and hid with the catering staff in the kitchen, who were peeking out the door to observe the carnage.


46. Leaving So Soon?

When I was in college studying photography, I got friendly with a fellow student who had a wedding photography business but was still studying to get his qualifications. After seeing my work, he asks me if I want to assist him at his next wedding. I agree to do so. The big day finally comes and I’m all prepared to go in and see the groom, the best man, the ushers, and a bunch of other participants to get some pre-event photos of them getting ready and whatnot.

To my surprise, the groom refused to be in any pictures, stating that he was feeling under the weather. I kinda thought he should just suck it up. It was his wedding day, after all. Nevertheless, he was insistent, so no pre-event photos were taken of him. A little while later, the ceremony comes and goes. It’s now time for the bridal party photos at the church.

Once again, the groom refuses to be in any photos, much to everyone’s annoyance. We all get to the reception, the speeches begin, and, midway through the father of the bride’s speech, the groom just straight up leaves. He once again repeats the fact that he was feeling a bit ill. This is where the bride drew the line—she went into a full-on rage. She started pulling the small groom and bride figurines off the top of the cake and stomping on them.

She shouted, “I knew I shouldn’t have married him!” There was a lot of hullabaloo at this point, with guests trying to console her. Everyone agreed that he was being dramatic and was basically a huge jerk. We got paid in full even though at that point we were done. I go home, put my feet up, drink a few beers, and then answer an unexpected phone call from my friend.

I was expecting him to just be calling to joke around a little bit more about how crazy that wedding had just been. Not even close. In reality, he was calling to inform me that the groom had passed shortly after leaving the reception hall, and that our photo job would now be turning into a two-for-one wedding and funeral service.


47. The Mac Daddy of Mess-ups

At the first advertising agency I worked at, one of our clients was an oil drilling company. I was working on some very standard ads for them, one of which had the headline, “FASTER, FARTHER, DEEPER.” I made a typo that caused the ad to read, “FASTER, FATHER, DEEPER.” Thankfully, my Creative Director caught it before it went to the client.

We all had a big (nervous) laugh about it and the original ended up on the creative department’s wall.


48. The Butt of the Joke

When I was a pretty young kid, around 12 or 13 years old I think, I had some weird stomach issues going on. They found some odd results with an X-Ray and told me that they wanted to do this pretty intense procedure on me to check my body out. So, I go into this room, and they tell me that they’re going to put a hose in my butt and fill my intestines with a milky liquid.

I looked terrified, and my doctor asked me what was wrong. To try and seem more mature, I told him that it sounded painful but that I was also very ticklish. I thought this was a great excuse to get around admitting that I was just shy about my body. He told me not to worry about it, as the procedure wasn’t as bad as it sounded. So a female doctor starts to shove this thing in 13-year-old me’s butt and I start awkwardly fake giggling. And then laughing. And then crying.


49. You May Now Take Their Thunder

At a friend’s wedding, in the middle of the vows when they reached the “through sickness and health” section, the pastor started going off on his life story—how he has had three wives and they all passed in horrible ways and so it’s important to really mean the “through sickness” bit. Then at the end of the wedding, before he announced them as a couple, he asked his fourth wife to stand up.

Really weird, everyone was looking around at each other to see if it was a joke or not. Groom was pretty mad.


50. Stranger Danger

I was watching a movie at the theater. I interlocked my fingers with the kid sitting beside me for a full minute. Turns out, he wasn’t my kid.


51. Don’t Bite the Hand That Feeds

Last year, I went to visit my friend Shirly after her brother had passed. Her brother passed by suicide after running the car in the garage. When I got there, there was another girl at the house, Lisa, who was eating a plate of food that Shirly’s mom had cooked. Before I got to the house, Lisa had apparently driven Shirly’s dad somewhere down the street—the family didn’t want to use the car that had been in the garage with their son.

Before Lisa leaves, she asks Shirly if she can have gas money for driving Shirly’s dad down the road. It was literally only a mile or two that she drove him, so it was mega stingy. But Shirly calls her dad into the room and says, “Lisa would like gas money for driving you today.” His response was just perfect.

Her dad looks at her plate of food and says. “OK, and I would like food money for the food you ate in MY HOUSE.” It was really awkward but I was proud of her dad.


52. Hairy Christmas

In high school, there was a kid who sat behind my friend in math class. He would play with her hair and whenever a hair would fall out, he’d keep it and stow it away in the battery compartment of his calculator until he had a little ball of girl hair. Then the year after, he got a pretty drastic haircut, saved all the hair in a bag, and presented it to her for Christmas.


53. Worst Stare Down Ever

I was very socially awkward in grade 10 after having been a recluse on my computer for about two years. I was aware of this, however, and was making an attempt at “coming out of my shell.” As it was the first year of high school, there were many new students who had come to my school, which goes from grades 1-12. One of the new students was an overweight girl who smelled of sweat.

This new girl was sort of ostracized by people because she acted strangely like when she once claimed that she supported animal cruelty. I was not particularly fond of this girl. Some guys in my class would make fun of her and laugh behind her back, but not always so subtly. The whole thing started in chemistry class when we were going to do an experiment.

I sat opposite to her at one of the work tables and somehow made eye contact. As stated previously, I was socially inept and, as such, I decided I would be friendly and engage her in a staring contest. She stared me square in the eyes and did not budge for a second. Not once did she blink and eventually, I gave up and looked away. Not a word was shared between us that day—but it wasn’t long before I seriously regretted ever looking her way.

Later that day, I get a friend request from her on Facebook. I accepted it and thought nothing else of it. But then, no more than ten minutes after having accepted, she added me on MSN. I accepted there too and asked how she got my email. It turns out it was in my contact info on Facebook, which I promptly edited out.

She wrote to me every day on MSN and I didn’t want to block her because that would just be mean, right? She would literally talk to me any time I was online and would sometimes send me offline messages. A lot of what she wrote was: “I’m bored, entertain me,” or “I’ve been looking forward to talking to you all day,” or some random question about me or why we didn’t speak in person.

Of course, I was beginning to clue in to what was going on. One day, she confessed her love to me over MSN, to which I, to the best of my abilities, respectfully let her down. I prayed that was the end of it, but the worst was coming. The next day, I spoke to two friends about it because I had no idea how to handle the situation. Later that day, she asked me if I had told anyone about it, to which I said I had spoken to two friends about it.

She didn’t believe me because apparently two guys in my class had been pointing at her and laughing at her. I felt it was wrong to say they did it because she was fat and ugly, so I claimed I had no idea why they did that. Of course, she didn’t believe me and proceeded to spam me with variations of “I HATE YOU” and suicide threats.

The next day, she came to school with bandages around her arm, yet proceeded to talk to me like nothing happened on MSN. A few weeks after that, mid-December, she wrote and asked me if I would let her kiss me just once before Christmas. I declined, said this had to stop, and proceeded to block her.


54. Mr. Postman

I used to work at a call center for a popular gift company. This one couple calls up and says “We need to cancel our order!” I look it up, and tell them UPS already has the order to deliver it. Then they tell me the horrific truth. They say, “You don’t understand. We are sending this to our son and his wife. We accidentally put his ex-wife’s name on the card.”

Obviously, that was gonna ruin Christmas. I was finally able to call UPS and get them to not deliver the package.


55. The Windy City

One time, I was at the doctor’s office having a lump on my private area checked. I described said lump to the doctor and he went about trying to locate it himself. I was lying down at this stage, staring at the ceiling while he felt around trying to find it. After about a minute of him fumbling, he admitted defeat and asked me to find it for him.

So I sat up and started to jumble myself around in my hands. I was hunched over and he wasn’t more than a foot away, staring intently at me, when suddenly a gust of wind blew the door wide open. Just then, a nurse walked past the door and caught a complete view of the situation. That was some awkward eye contact between us…


56. A Pat on the Backside

When I was a kid, we were on holiday and decided to go to a church. While we were there, I decided that I would be funny if I would slap my dad’s butt with both hands. So, I ran in full speed to maximize the impact of the slap. I ended up slapping a stranger who also happened to walk next to a woman with a stroller in his hands which made me think it was my dad.

Then it got worse. My parents saw it as well. Because people are asking what happened afterward. My parents just laughed at me, which made the guy laugh as well and then we just left the church, I think.


57. Message Failed to Send

As much as you can call someone a stalker in high school, I had one and I always treated my “stalker” with respect even though it was weird. She would follow me around school, give me these love letters, draw pictures of us together, make me these homemade bracelets and necklaces, call me up at the most random times, she even had my private email address.

I tried to let her down easily multiple times but she didn’t give up. One time she appeared at my house crying, I had to take her in and stop her from crying. She would occasionally call up crying and I’d have to talk for hours on end to try and calm her down. One day I just had enough, so I told her as directly as possible while still trying to be nice, “I’m sorry, but I’m not interested okay…?”

She disappeared about a month later, literally left the country. Two years later she came back, I added her on Facebook and she told me she was sorry, talked to her a while and she seemed to have lost her craziness, she now has a boyfriend.


58. Nipple Trouble

When I was a teenager, my friends and I would spend the weekends staying up late playing video games and eating junk food. I was also a cross country runner, and on this particular night, I was experiencing some extreme chafing from a long run earlier that day. While we were at the gas station getting Doritos and energy drinks I announced to who I thought was my friend, “Man, my nipples really hurt.”

Upon realizing it was a complete stranger with whom I had just shared this intimate detail I simply stared at him and said “You’re not my friend” and walked away. I didn’t go back to that gas station for a long time.


59. Not Every Achievement Needs to Be Aired

At one wedding, the bride’s older brother gave a speech where he talked about how he changed her diaper when she was a baby. He then told the groom that because of this, he (the brother) “saw her first.” It was super gross and cringy.


60. There’s a First Time for Everything

Getting my very first pelvic exam was the most awkward experience I have ever had in a doctor’s office. The doctor was new and she was extremely nervous. As a result, she dropped the first speculum while trying to get it out of the package. Her hands shaking and everything. Umm, okay? That didn’t exactly calm me down…but it was going to get even worse.

A few minutes later, I’m on the table, speculum inside me, doctor and nurse hanging out around my lady bits. I’m trying to pretend that I’m not here when the doctor suddenly goes: “Are you on your time of the month right now?” I replied: “No. Why?” She went: “Oooohh…” Apparently, in her nervousness, she had been way too rough and made me bleed. Thanks, Doc!


61. Can’t Chill

I’ve been crushing on the same dude for a while. It was a super-hot NYC summer and I bought a new AC and texted him, “This AC is the only adult toy we’ll ever need.” Then, he ghosted me for a year.


62. Music Makes the World Go Round

I once attended a wedding where the bride and groom sang their vows to each other. Neither of them had a singing voice. The vows were also totally crazy and inappropriate. She promised to do whatever he wanted in the bedroom, and he promised not to always ask where she was going whenever she left the house.

The autotuned microphones were also a terrible idea. Their vow songs shared a chorus and it was awful, yet they expected all the guests to sing along with the chorus. The singing of the vows lasted more than twenty minutes. Calling it twenty minutes of pure cringe would not be an exaggeration to anyone who was there. Kids, don’t sing your wedding vows!


63. Not Everything Is Better out Than in

I do a workout camp with a group of people. I just started in January along with this other girl, Natalie. From our first work out, there was something about her that kinda rubbed me the wrong way. She struck me as the girl who would make the meeting last longer because she won’t shut up. A couple of weeks in, she missed a workout or two. Well, the following week, she was back.

Camp was done, I had become friends with this woman, Susan. She and I were walking back to our mats, but I got ahead of her and that’s when Natalie, out of nowhere, accosts Susan. Literally what she says is, “Yeah, so, I was on my way to camp on Friday and I thought I had to pass gas, so I did…and I wound up pooping myself.” All Susan could say was a shocked “Oh…no.” Because why the heck is she sharing this?

But Natalie wasn’t done just yet. Not by a long shot. “Yeah, and I don’t know if it was because of the smell or actually being sick, but I wound up throwing up, too. So, I had to drive home in my own diarrhea and vomit. Charles had to clean the car. It was awful.” Susan said she was glad she was feeling better, Natalie left.

I asked Susan, “Did you do anything to welcome that?!” Susan yelled “NO!!!!” And then we cackled because OH MY GOD. Several months later, we were at camp when Natalie walks up to me while I’m sitting on the ground, turns around, sticks her butt in my face, and says, “Can you tell my pants are wet?” I said no. And that’s when she told me she thought she could hold it but peed herself on her way there cuz she sneezed…and then she says, “Well, if you smell something, it’s probably me.”

Sweet god.


64. Kiss and Break up

My husband and I were invited to his friend’s wedding last summer. They’ve known each other for a decade, went to college together and now work with each other. The wedding was lovely, and they had an open bar before dinner. During the reception, they were doing this game where everyone had to stop eating to watch each table answer trivia questions about the bride and groom or whatever.

Our table got it wrong, which meant spinning a wheel to get a punishment. Things like do a dance, etc. So, the wheel lands on “kiss.” The groom thinks he’s going to be funny and picks my husband, and after a lot of thought, another of their college friends. My husband hasn’t seen this dude in over ten years. They made brief eye contact and nodded at each other. The groom went pale.

Then BOOM, my husband and this other dude launch into each other’s arms and start kissing. Sloppy, noisy, face licking, grabbing, making out maybe 20 feet from the grandparents’ table. The other guy’s wife and I were cheering them on. The best man was collapsed laughing on the table. The groom could only watch in open-mouthed horror. The bride was furious.

The pictures are amazing, though.


65. Slapping the Teacher

This happened in grade nine. I don’t know why but me and my friends would play this stupid game where we would try to sneak up on each other and slap the back of our heads as “our way” of saying hey. I spotted my buddy Rhys at the end of the hall and snuck up the best I could and wound up a home run slapper. It all went so wrong so fast. 

He noticed last second and ducked. I ended up slapping the heck out of my teacher’s boob as she turned the corner. After the slap, it felt like time was frozen. Kids in the hall all just stopped what they were doing and the teacher just kind of stood there in shock. I was so embarrassed I cried. In the hall. Surrounded by kids from my grade.

Then I got sent to the principal’s office, where I got a one day in school suspension for “hitting a teacher.” I think the punishment was so light because the teacher felt sorry for me. The phone call to my parents explaining what happened sucked. My mom was just disappointed in me—in some ways that just made it worse—and my dad just kept laughing.

I got called “boobie” for two years. I’m 23 now, but my friends still bring up that story.


Ground Had Swallowed Them factsKristina Dimovska | Factinate

66. What Happens in Vegas…

When I was 18, I went with my then-girlfriend to Las Vegas to meet her parents; we lived in Florida. I found out that her dad and mom lived in separate houses right across the street from one another for whatever reason, which was strange but definitely not the strangest thing that would happen that trip. Her dad came over to her mom’s house to meet me, and I couldn’t help but notice he was dressed in a suit.

I thought maybe he was just a fancy dresser. He kept asking me questions about my family and how I felt about his daughter. He seemed to like me, and we went through the trip on fairly pleasant terms. Once we get back home to Florida, my girlfriend told me the truth. She tells me that her dad thought we were coming out to Vegas to get married, and he dressed up because he was planning on taking us to get married that day.

She had to tell him that we had no intention of doing anything of the kind. Like, what?


67. Movie Magic

I was in high school and the girl I had the BIGGEST crush on lent me a movie. We had a senior day at an arcade and she gave me the movie then. She reached into her purse and grabbed it out. I was already kind of awkward but we hugged and I left. I took the movie and threw it on the passenger seat. It rattled like candy in a box so I took the movie out of its case and found her birth control.

I knew what it was but I called her and played dumb. Her friends laughed hysterically and I just said here’s your drugs. Both of our faces were red and we walked away quickly.


68. No Kids Allowed

My place of work has a 21 and over policy after 9 pm, and a group of people walked in. I immediately assumed they walked in with their child because I couldn’t see her over the counter. So I said, “Hey guys, I’m sorry but we’re 21 and over right now.” It turns out she had dwarfism. Oh my lord. I was so incredibly MORTIFIED.


69. How Do You Like Them Apples?

I once attended a wedding for a couple who had bought an apple orchard to live on after leaving the city, to live a simpler life. They really doubled down on the apple theme at their wedding. There were apples everywhere. On the tables, in baskets all around the venue, on the podium where they got married, pictures of apples hanging everywhere, small fake trees with apples tossed under them, etc.

For cryin’ out loud, the priest marrying them even had an apple tie on! To make matters even more ridiculous, there were apples somehow incorporated into every single dish that was served at the reception. The wedding cake was even shaped like an apple. It was really bizarre and unnecessary. They ended up selling the apple orchard a couple years later because they had no idea what they were doing.


70. Make a Run for It

Back in primary school, I had a crush on a girl. Her younger brother was kind of a friend, so I’d hang out at their place every once in a while. But thinking it would be weird to ask if I could hang out, I’d go for a run past their place and hope they’d notice me and invite me in. It worked, but most times I had to turn back and run past at least 4 times before they’d invite me in.

I wonder how many times they actually saw me doing this.


71. Don’t Go Breaking My Heart

In elementary school, there was this girl who would constantly get beat up by this kid. He would torment her every lunch. I saw this a few times and saw that she was defenseless against him. I wasn’t a big kid, but I was bigger than the guy beating her up. I ended up fighting him off of her a few times. I even pinned him down and let her punch him. He stopped picking on her after that.

Then in junior year in high school, I’m at winter formal and I’ve already split from my date. We weren’t really interested in each other at all, we just went with each other so we could go. She’s standing alone and it turns out that her date ditched her. I end up taking her to the dance floor and dancing with her. We hit it off and just have fun on the dance floor.

We ended up hanging out later and I learn that she has been crushing on me since elementary school. She had built this image of me in her head as her prince charming/white knight. I never did those things with the intention of getting laid. I just didn’t like seeing someone defenseless and being picked on like that.

She was decently attractive and a nice girl, so I just went along with it. She eventually realized at some point that I was not as into her as she was into me. She told me that she is fine with just hooking up and not letting it get serious. We start making out and things start to get crazy. She suddenly tells me to stop. I stop.

She then says that she doesn’t want to go through with hooking up with me. She explains that she had built up this fantasy of it in her head and she didn’t want to ruin it with reality. I told her that I understood and I took her home. I cut contact with her because I realized that I’d just be using her if we hooked up.

It wouldn’t have been cool for me to mess with her emotions like that. I already did it enough already.


72. The Mix-Up

When she was younger, my mother came for a routine pregnancy exam at the hospital. It wasn’t her usual gynecologist because they were on holiday. As the replacement enters the room, she’s waiting with her two feet in the stirrups, wearing the typical hospital grown with the opening at the back. He revealed the instruments for the exam.

My mother was a nurse. She recognized the instruments, and she knew something was wrong. They were abortion instruments. She questioned the doctor about it. His response was chilling. He stiffly said, “Well yes, as you know the baby is gone, we need to remove it.” At this point, she realizes they’ve mixed up the files…but she’s just getting started.

Shee threw the biggest tantrum in the history of tantrums. My dad usually picks up the narrative at this part of the story, “I saw your mother storming out of the exam room, she passed by me as she was howling, ‘WE GO, NOW!’ with her clothes in her hands and her exposed butt.” It’s a great image, and that doctor probably never lived it down.


73. Does the Missus Know About This?

I once accidentally showed an explicit photo of my fiancé to a receptionist. It was my first time on site and I needed to show him a pic of where I’d be working as I didn’t know where it was on site. So, I open my gallery and lo and behold, my missus’ naked body was right there. I just stepped back and apologized, but he didn’t say anything…


74. Poorly Handled

Without thinking, I once tried to shake an amputee’s hand. He stuck out his arm in a non-offended way to show that he was unable to shake my hand, and to diffuse the situation with only minimal amounts of awkwardness. Then I made it so much worse. For some reason, I took this as a gesture to shake his handless arm which resulted in uneasy laughs and goodbyes.


75. The Groomsman and the Phantom Womb

Went as a date to a wedding of a family I didn’t know. The younger brother of the groom caused the ceremony to be 20 minutes late. They were running behind and getting no response from him, so they started the ceremony. He came in in the middle of their vows and announced “Sorry I’m late, but I just found out that me and his girlfriend are having a baby!”

No one said anything, and someone told him to sit down and be quiet. After the wedding ended, I asked my friend what that was about and she told me that the brother was a known attention-seeker and everyone was sick of his garbage. A few weeks later she gave me another update straight from the groom. There was no girlfriend, and no baby either. He’d made it up.


76. Incoming!

When I was about 13 I went on a school trip which included a boat ride. It was a windy day and the sea was rough, so like most of my friends, I got extremely seasick. The toilets were full of puking school kids so when it was my turn to churn I found a space along the rail and let loose. I aimed down at the sea but the wind whipped my vomit about 20 feet horizontally straight over a middle-aged man who was enjoying the sea air.

As I watched in horror, he registered that he was being spattered with something, but it was only when my second wave hit that our eyes met and I saw his face change from confusion to horror. I had no words, just more vomit, so he hurried off—presumably to clean himself. Thankfully I didn’t see him again but I’m sure I ruined his day.


77. Together Again

I once attended a wedding in the United States. This was both the bride and groom’s fourth marriages. To each other. Yes, they got married to each other four times and divorced each other three of those times. They picked a dirty motorcycle bar for the venue of their fourth wedding. They were openly giving young children adult drinks, then laughing at them for being intoxicated.

Things were weird enough to begin with, but they soon reached a whole new level of insanity. I asked my friend if I could leave after the bride pulled a knife out of her dress and tried to stab the groom with it for having slept with another woman while they were divorced. I’m not sure if this is common in New Jersey. Other weddings I attended while in the USA were not like that…


78. Poor Choice of Words

My son had small Toy Story figurines but wanted big ones for Christmas. I walked into Toy R Us and asked the male clerk, “Do you have a large Woody?” He turned bright red. I wheeled around and marched out and didn’t go back for months.


79. Do You Really Want to Hurt Me?

One day when I was in kindergarten, there was a girl who I had a little crush on. At least as much of a crush that a five-year-old can have, I suppose. The teacher summoned us to the floor area, where she sat on a chair to read to us. I wanted to sit next to said crush, but she wanted to sit next to her friend. What did my rational five-year-old mind do?

Cry. Yep, I bawled my eyes out because she didn’t want to sit next to me. Naturally, the teacher stopped and asked me what was wrong. After my blubbering story about her rejecting me in front of the whole class, she forced the girl to let me sit next to her.


80. Always Destroy the Evidence

One of my best friends had a radio show on our university’s station. I liked a guy in one of our classes, and my friend and I thought it would be clever for him to interview me off-air about my interest in that guy. We then put the interview on a disc and gave it to him. Well, the feeling was not mutual. I graduated five years ago and I’m married now, but this still makes me cringe so hard.


81. A Teacher Gets Schooled

I’m a teacher. I had a particularly difficult student who gave me a very hard time on an unusually hard day, early in my career. After class let out another colleague stopped by and without thinking, I said, “Nobody wants (“that difficult kid”) in their class! It’s hopeless.” I turned around and went white as a sheet. He was walking in the room to apologize and heard me.

However withdrawn and difficult he was before this, it multiplied tenfold, and I felt terrible. I tried to apologize to him, but he didn’t want to hear it. After that, I didn’t breathe a negative word about a child on school grounds. As an educator, you have to learn sooner or later that your students are the ones who get to act like children. Not you.


82. Not Strawberry Much

When I declared to my crush that I liked her. she asked me why I liked her and it was hard for me to explain. After that she compared me liking her to why people like strawberries, there doesn’t have to be a reason. Then she told me liked me only as a friend. My siblings laughed like crazy when I told them this story.


83. Out to Lunch

I once had a pizza delivery guy walk in on me while I was getting a pelvic exam at the OB/GYN. My feet were up in the stirrups and my doctor’s hand was in my you-know-where. Yeah, the whole bit. Apparently, the nurses had ordered a pizza and directed the guy to bring it to the break room, but he accidentally opened the wrong door.

You’d think that if you know you’re at an OB/GYN’s office, you would have the common sense to at least knock before entering any closed rooms, right? Yeah, no. It happened so fast though that he couldn’t have really seen anything. I’m also pretty sure that he was more embarrassed than I was. Still, I must admit, this whole thing sounds an awful lot like the plot to a cheesy adult movie.


84. Tears of Joy?

The most awkward wedding that I’ve ever attended was one where a friend got married to the boy her parents had made her break up with several years before due to family and cultural differences. Her mother in law full-on sobbed throughout the entire ceremony. We all just had to sit there and awkwardly watch it. There weren’t even any drinks to blame the behavior on, as drinking is against their family’s religion.

Other than that, the event was beautiful and the food was awesome!


85. Separated from Reality

I was in love with this boy. We were seniors in high school and after a fun day together at a choral festival where I performed and he was a part of the stage crew, he gave me his number. He called the next day. We spoke for hours. He brought up that he and his dad had moved here from Florida. I asked, “Oh, really? I always thought the kids would go with the mom in a divorce.”

Then he said, “They’re not divorced.” In my horror, I just ask, “What? Is she dead?” And after a long pause he just says, “Yeah.” I wanted to crawl into a hole. I tried desperately to salvage the call, but ended up figuring I’d never see him again. I saw him the next day at school. He smiled and patted me on the head saying, “I get it. You had no way to know. We’re good.”

We’ve been married for 20 years now.


86. Popping the Question

When I was brought back from being under anesthesia after getting my wisdom teeth out, before my transportation back home arrived, I recovered enough to unplug my IV and various sensor thingies and wander into the waiting area to ask strangers to sleep with me. The nurse promptly gathered me back into my room and I recall complaining that someone might have said yes and I deserved the right to know.


87. Adventures in Babysitting

I used to babysit a three-year-old when I was in high school. It was her birthday and her dad invited me. I bought her a stuffed snake, since she was into snakes, and some helium balloons, and showed up a few minutes early in case the parents needed some free babysitting while they set up. I get there, and nobody is there except the mom and the three-year-old.

So I play with her and supervise while the Mom ignores I exist, which is cool; she scares me anyways. About an hour goes by, things are getting a bit awkward, nobody is showing up. I’m in their house being in the way, but leaving now would be rude, so I wait around. Finally, kids and family show up, the kids are upstairs, all these adults are sitting around the living room.

And nobody acknowledges I am there. I smile and try to say hi but people just look away. So I stand in a corner by the stairs waiting to be thanked so I can leave. And about another hour goes by, me just standing right there in the corner of the room, about five feet away from everyone, awkward as heck.

The dad shows up and he stands right next to me, staring into space, sipping a drink. I try to chat with him, but he just nods and stares off into space, ignored by the rest of the people as well. Finally, I’m thinking “screw this, so I announce I have to go, everyone just stares for a second, then turns away. So I just walk out of their house. No thank you, no bye, no hello, no offer of food or drink, no offer to sit down.

Never forgot it.


88. The Original Captain Underpants

When I was a young kid, we had a pajama day at school. Well, I always just wore my boxers to sleep. So guess what? I showed up to school in pretty much nothing but underwear. Why my mom allowed me to go in that way and even drove me there, I have no idea. It was the most embarrassing day of my life, and the school had to call my parents to come pick me up.


89. Breach of Contraction

With our second child on the way, my wife wakes up one morning with contractions. This happens to be the same day that she had a scheduled appointment with the doctor to check on her progress. So, we just kept that appointment. We meet the female doctor in the clinic, across the parking lot from the hospital.

I’m in the exam room and the doctor is checking my wife, who’s up in stirrups. “Oh, yeah, you’re pretty dilated and effaced. Today is definitely the day.” I’m sitting nearby, politely averting my gaze, when the doctor says, “Your bag of water is bulging, too. I bet I could, uh oh!” Right away, my wife starts laughing nervously.

I look up to see the doctor, two fingers deep in my extremely pregnant wife, trying desperately to prevent the now-broken water from flooding the exam room. She stretches out to reach a bottom drawer, and some amniotic fluid kind of sprays out in odd directions. The doctor has me get some absorbent pads out of the drawer and lay them down as quickly as I can before she removes her fingers and jumps out of the way.


90. Leave a Part of Yourself in the Book

I once saw a teacher pick her nose while reading from the textbook and everyone saw it.


91. So You Think You Can Dance

A friend wanted me to find a date for the formal our fraternity was having. I asked a few girls and they had other things to do. So I called the girl who I usually danced with at a few dances. She picks up the phone, I reply who I am and ask if she wanted to go to the winter formal that was coming up. I overhear her say to her roommate, “It’s that stupid boy who always asks me to dance.” She agreed.

Fast forward a few months later, and I got introduced to her roommate. As soon as I can, I tell her, “I was the stupid boy who kept asking your roommate to dance.”


92. It Runs in the Family

Back when we were 17 or 18, my boyfriend and I were in his room one day, just watching movies and chilling. His mom walks in and asks to talk to him, they both go out into the living room, and she proceeds to rant at him about how it’s not normal for us to spend so much time together, and how she didn’t like that we had been in his room all day.

Meanwhile, I’m alone in his room, and can clearly hear the whole conversation. I gather my nerves and all my stuff, walk out to them, and say, “Matt, I’m going home, would you like to come over to my house?” The mom interrupts with, “We’re actually having a conversation here,” so I just say goodbye and walk out the door.

His sister, who thought the conflict had somehow been initiated by me, then made it ten times worse. She chases me out of the door screaming, “YOU WITCH, YOU RUINED MY FAMILY!” I was pretty shocked by this and didn’t respond; I just got in my car and drove home. A few minutes later, my boyfriend shows up to apologize for his family.

It didn’t end there. A few minutes after that, there’s another knock on the door. Yep, his mom had followed us to my house and asked to talk to him outside. He told her to go home. This all happened a few months before we both moved away to university, so I just didn’t go to their house again. We’re now in our 20s and still together. His family is still crazy and he agrees.

Luckily, we now live five hours from them.


93. Lightweight Champion

When I was about 12 years old or so, my doctor knew that I really didn’t like needles. So, he put a shot that I needed in his pocket with his pens so that I wouldn’t notice it and get my guard up. In the middle of a sentence, he pulls it out and comes at me. Terrified, I punched him directly in the face and broke his glasses.

It wasn’t intentional, per se. The dude was coming at me with a sharp object. I didn’t even have time to process what was going on. It was all instinct and reflex. He ended up grabbing me by the shoulders, pinning me down, and doing the injection. I can only imagine what he must have been thinking. For years afterward, I couldn’t bear to face him.


94. Irresponsible Faculty Meeting

One of my favorite moments:

I walk into the school office to check my mailbox. A parent of one of my students sees me and says very loudly, almost screaming, “Oh, FINALLY!!!! LOOK, EVERYONE, I FOUND A TEACHER!!! Do you realize that I left work EARLY to come here after school to talk to my son’s teachers about his report card, and you are LITERALLY the ONLY teacher I have found?!!! I went from classroom to classroom and everyone is GONE!!! Do you know what time it is?!! It’s 3:45 pm! School ended FIFTEEN MINUTES AGO!!! FIFTEEN MINUTES!!!! And you’re the ONLY teacher STILL HERE!!!! CAN YOU EXPLAIN TO ME WHY EVERYONE IS GONE?! CAN YOU EXPLAIN TO ME WHY EVERY TEACHER HAS LEFT THE BUILDING WHEN SCHOOL JUST GOT OUT?!!!!”

I paused, waiting to see if there was more. When I realized he had finished, I said, “All the teachers are in the library. We’re having a faculty meeting.” The look on his face was priceless. He knew he was in the wrong, but by that point, he had committed so fiercely to his anger and righteousness that he couldn’t just apologize. So he said, “Well that’s just irresponsible.” And he walked out of the office.


95. Her Own Secret Admirer

My cousin’s friend came over to stay for a few weeks. She was very vain and before she left, she wrote a note to my uncle (who is friendly to everyone). It was the most awkward letter ever. In it, she’s saying how she had to sadly reject him, even though she knows how much he is secretly in love with her. We all found the note together after she left addressed to him (he was with us and opened in front of us).

He was creeped out.


96. A Romantic Evening

I once tried to make love in a hotel bathtub. The bathroom was very small, there were no lights, and the faucet was leaking. Also, our golden retriever walked into the room and decided to come sit with us—and entered the bathtub while the act was going on. It was definitely one of the weirdest nights of my life, and is never to be spoken of again.


97. What’s in a Name?

I once went to a wedding where the bride and groom surprised everyone by announcing that their ceremony was also going to be a “Name Reveal.” In other words, they were informing all of their closest friends and family members that, as a married couple, they were going to be changing their last name to something totally new so that they wouldn’t be “stuck to their heritage” or have anything “holding them back.”

Turns out that, in reality, they had changed their name thinking that doing so could erase their mountains of debt, or at least hide themselves from those trying to collect on it. However, it wasn’t too long before they quickly learned that the government doesn’t tend to allow you to live under two separate identities…


98. No Really, Oh No

Working in an online gambling chat room. Dude comes to take me off my break and comes in the room. At that point, a player had told us his brother had just passed on so I said “Oh No!” Dude taking my place sees this and gives a big “OH YEAHHHHHH!” kool-aid guy style.


99. Doing Things the Old Fashioned Way

I was at the doctor’s office for a physical exam before my freshman year of college. The doctor was this assertive and intimidating female, and it came time for the hernia check. Now, for my whole life, this procedure has always involved the doctor cupping my private area and asking me to cough. However, I guess they only need to feel just above the private area these days as opposed to the area itself.

I was not aware of this fact at the time—and it led to the most mortifying experience of my life. So, I’m sitting on the exam table, and the doctor asks me to unbutton my pants for the hernia exam. I was completely ignorant to the fact that they didn’t need to actually come down. She then turned away to go get a glove. At this point, I pulled my pants down to my knees. She walks over with a perfect poker face and calmly places her hand on my lower stomach and asks me to cough.

She checked both sides twice. The entire time, my privates were needlessly exposed. She never said a word about it or even acknowledged that fact. I guess I got lucky to have that particular doctor on that particular day. If someone a little more emotive had been the one checking me, I might never have lived down the embarrassment.


100. Fake It til You Make It

In my university days, I had been invited to a keg race. And I don’t want to brag, but my team won. Next thing I know, everyone is up on the roof. I’m sitting up there, cut as anything, when the overwhelming need to pee hits. My loaded brain thinks, “I got myself up here! I can get down too.” I go over to the edge of the roof and see that there is about half a meter between the house and the fence with some large bins sitting there.

“Ok,” I think to myself, “gently make your way to the bin, use the fence as support, small drop down, we’re fine!” That was the plan—it turned into a disaster almost instantly. The execution was that I just stepped off the side of the roof, bounced my way down between the fence and the house, and landed in a pile on gravel right in front of the guy I had my eye on and thought was really cute.

I remember it clearly. He was just walking and a loaded girl just falls from the sky right in front of him. He went, “Oh my god, are you ok?!?” I jumped up, cool as anything, a confused look on my face as I said, “Yeah? Of course. I’m fine?” as if I do this all the time and it didn’t hurt at all. For the rest of the party, everyone kept coming up exclaiming they heard I fell from the roof.

I got my friend to pick me up and had to make him pull over so I could vomit. The next day I could barely move.


101. Save Some Cringe for the Rest of Us

A female friend of mine–to whom I was admittedly attracted–had been expressing her reservations about an upcoming vacation with her family. Though it wasn’t being overtly presented as such, the trip was meant as a way of re-solidifying her parents’ marriage, which had been more than a touch rocky at the time.

They would all be driving from San Francisco to a small town in Northern California, where they’d stay at a bed-and-breakfast inn for a weekend before continuing northward for some unknown destination. In keeping with the alleged purpose of this so-called vacation, two rooms had been booked at the inn in question.

To her dismay, though, my friend discovered that her mother would be occupying one room, her father would have the other, and that she and her sister would each have to bunk with one of their parents. This was worthy of lament on its own, but it was made unforgivably worse by the verbal diarrhea that I offered in an attempt at providing comfort:

“Aw, it won’t be so bad!” I told my friend. “Your father will probably enjoy sleeping with you.” A moment passed before I realized what I had said. Then, with a feeling of growing horror, I tried to explain myself. Suddenly, I made it 10 times more awkward. “Wait, I didn’t mean it like that!” I hurriedly said. “I mean, like, he’s probably sick of sleeping with your mom.”

“No, wait, I mean… I just mean that he wants to spend some quality time with his daughter.” If I had stopped there, I might have been able to salvage the situation, but as it happened, I decided that the best course of action would be to keep talking. “I can’t say that I blame him, really. I’d love to sleep with you.” She and I don’t talk much these days.


102. Spellbound Curse

I purposely would walk to my classes the same routes that I knew this cute guy took. One had these set of stairs that I would pass him going down while I was going up. One day on I zoned out looking at him and next thing I knew I tripped faceplanting. My stuff went everywhere and insult to injury, he kept going while laughing at me.

Another time I saw him outside a K Mart only to zone out again and walked right into a pole with my face. He was just that mesmerizing! Seriously it had nothing to do with the mating call of a socially awkward girl.


103. Her Special Day Was Special, Alright!

My best friend’s wedding. As his soon-to-wife was being walked down the aisle by her father, he managed to trip on her wedding dress, theatrically spin around, grab the hat off someone’s head as he clutched at anything to hold on to, and pull his daughter down on top of him, breaking her nose with his forehead in the process.

Everyone, of course, rushed to their aid. Me, on the other hand—I fell to the ground absolutely laughing my head off. As she was being rushed away, I was still rolling on the ground laughing while everyone just stared at me. Just because I was the best man, doesn’t mean I’m a good man. The video still gets pulled out from time to time and I still lose my mind every time.


104. A Lot of Energy in This One

My brother managed a gas station about ten years ago and had hired the soon-to-be bride as an employee. A little while into her employment, she requested a few days off for her wedding. The date was still a couple months out, so it was no big deal. About a week before her requested time off, she came into work and had the following exchange with my brother:

Bride: “Wanna see my new tattoo?” Bro: “Uh, sure.” She lifts the back of her shirt to reveal a huge, green, Monster Energy “M” covering the whole upper half of her back. Bro: “Holy moly! Wow!” Bride: “Awesome, huh? And my fiance got the same tat!” Bro: “Really?…” Bride: “I know, I know what you’re thinking. Copyright, right?”

“But what are they gonna do? It’s already on my body! It’s ALREADY ON MY BODY! Ha ha!” Bro: “Right. That. That is what I was thinking.” Then, at the ceremony, the pair awkwardly gave the same demonstration to all their guests. There are even pictures of it. I’m working on getting a hold of those. It was a camouflage themed wedding.

She had an open-back camo gown with camo heels. She even had a camo veil. I really wish it had been ghillie suit headgear. The groom had camo pants with camo boots and a camo bowtie. He was, indeed, shirtless. He did wear a camo ball cap, though. I imagine them walking down the aisle, backs glistening in the sun with vaseline over a huge Monster logo.

Just the perfect day that every kid dreams about someday having. They were happily married for seven months.


105. Threat Level: Midnight

I have a friend who is basically a young Michael Scott. Seriously, sometimes when watching The Office, I cringe not because of what Michael is doing, but because it reminds me so much of my friend. One day, our group of friends got on the topic of what Office character we’re most like. He loudly and immediately declared he thinks he’s most like Ryan…


106. A Picture Is Worth a Thousand Words

My family and I were watching a program on TLC about cavemen. There were actors dressed up like cavemen doing caveman things, as the narrator explained the scientific theories of what they thought their lives were like. My sister was just in awe watching this. Mouth slightly open, eyes open wide. During a commercial break, she asked the room, “How did they get the cameras back then?” We all just stared at her…


107. Taking a Morning Flight

I once had to go to the doctor for a routine smear test as a student. I hadn’t slept the night before, as I’d been partying hard. I was still not quite with it by the time my appointment came around in the morning. The male doctor hadn’t performed a smear before, and for some reason, a nurse was called in to witness the procedure.

Predictably, the doctor had trouble finding my cervix and the nurse told me to roll my hips up. The doctor was visibly getting more and more nervous—and then I managed to make it so, so much worse. To break the ice, I started singing the old Rawhide theme song. “Rolling rolling rolling, keep those doggies movin, Rawhide!” I know this sounds like a ridiculous thing to do, but for some reason, it made sense in my head at the time.

Then, I started to laugh uncontrollably at my own joke. This caused the doctor’s speculum to come aggressively flying out of my hooha and shooting straight towards him. It hit him right in the face and knocked his glasses off. I was totally shocked and embarrassed and did not have any idea how I should react. The lab results ended up coming back inconclusive.


108. A Case of Mistaken Identity

When I was about 12 years old, I had to go to the hospital to have my appendix taken out. It was the first operation of any kind that I had ever undergone and I was very nervous. The doctor had asked me to tell him or a nurse when I passed gas. I guess this would be a sign that my bowels were starting to wake up from the anesthesia or whatever.

Well, I woke up late at night that evening and passed gas. I saw a guy in white passing by, so I called him over and said, “Excuse me, I just passed gas.” With a confused expression on his face, he said “Okay. Well, you should probably tell a nurse.” He then continued mopping the floor. Yes, that’s right. I needlessly announced my flatulence to the janitor.


109. Family Friends With Benefits

I have a regular breakfast place that I had been frequenting on the weekends for about a good five or six years. One day I went into work later because of a doctor’s appointment, so I decided to pick up some breakfast at my regular place. I walk in and I take a look around to find a spot to sit at and I see my dad. As soon as I saw him, I had a bad gut feeling.

He’s sitting in a corner spot with some woman I don’t recognize. He looked shocked and I decided to walk over. He stands up and gives me a kiss/hug and introduces her as a coworker. It was the most awkward introduction of my life. My dad was an AC Repairman and was strictly on the road. No women in his office.

I pretended like I believed him, said hello and sat down on my own. Definitely one of the most awkward moments of my life that will stand out for a long time. More background: My mom and dad haven’t been together since before I was born however, he was married to another woman when this took place.

The waitresses were all my friends and a couple of days later when I went for breakfast, they proceeded to tell me how he met that lady there every week. I never brought it up to him and pretended it never happened. That was about 14 years ago…I still go to that breakfast place and the girls told me after that day he never came back to that restaurant.

In a couple of weeks, it will be one year since he passed. I’m glad I got this opportunity to think and talk about him.


110. Leaving the Doctor in Stitches

When I was about 18 years old, I went into the doctor’s office because I was experiencing some extreme nausea, among other things. He kept asking me if it was possible that I could be pregnant, over and over again. “So, uh, could you possibly be pregnant? Maybe we should run a pregnancy test.”

“Pretty positive I’m not,” I responded. He then asked, “When was the last time you had intercourse?” I replied, “Uh… never?” He started laughing and shouted out, “NEVER?!” At this point, he suddenly whipped his head around to face me from behind his clipboard. “Oh, haha, wow, I had no idea. That simplifies things a lot!”

Was that really necessary??


Sources: 123456

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