There’s nothing more awkward than having your future father-in-law find your naughty toys…or is there? These hilarious stories show us that appearances can be very, very deceiving. And sometimes, it’s exactly what it looks like—or much worse. Get ready to blush with sympathetic embarrassment and cackle with nervous laughter. These people are shameless.
1. Papa, Don’t Preach
I had recently started dating this girl. We had been together for maybe three months and I had yet to do the "meet the parents" thing. I had been putting it off as her dad was this fearsome Scottish dude who was known for his temper. Anyhow, at my 19th birthday party things got out of control. It was supposed to be a garden party, but it changed to a garage party when the weather let me down.
As my parents didn’t want a mess, everyone was supposed to take off their shoes when going into the house to use the toilet. As you can imagine, after everyone broke their "seal" the first time, they couldn’t be bothered going inside and being diligent. So, we ended up going through the back gate and using the grass around the corner as an…outhouse.
With all of the foot traffic and the rain and the pee, it did not take long to turn that patch of grass into a stinky quagmire of mud and muck. My girlfriend definitely partied too hard and couldn’t keep her drinks down. Then disaster struck. She dashed outside to the "outhouse" to vomit and hurled up everything she had in her stomach. And then she fell face-first into it.
She managed to stagger to her feet but at that point, she looked like the swamp thing and she is going downhill fast. Now, she was under strict instructions to be home by midnight, and it is was 11PM at that point and she could barely stand. My first idea was to get permission for her to stay over so I called her house.
Of course, it was her dad who answered the phone. My request went down like a brick sandwich and he gave me a very firm "NO!" before hanging up the phone. So, I had to call back and sheepishly explain that she was too far gone to travel home and that he would need to pick her up. He shouted, "FINE!" into the receiver before slamming the phone down.
It was then I knew that I really made a mistake…she still looked and smelled like something that crawled out of a swamp. And her dad would be showing up at any minute. I knew I had to clean her up. We (me and her best friend) had already gotten her out of her jumper but we still had to get her into clean clothes.
We took her to washroom to clean her up and I guess I didn’t hear when her dad arrived. He just walked straight in. Someone must have directed him upstairs. He walked into the bathroom just in time to see myself and her best friend struggling to put clothes on his daughter but it must have looked to him like we were taking them off.
Fortunately, with her best friend there, she was able to explain what had happened and her dad didn’t drown me in the toilet. A year later, they had me over for dinner.
2. Freeze Punk!
As a broke college kid, one of my go-to meals was a $0.69 chili dog from 7-11. There was one just four blocks from my dorm but, being a broke college kid, I had no car. One winter's night, I just couldn’t fight the temptation to get one those chili dogs. So, I bundled up in my heavy coat, gloves, and beanie and went to get myself one.
It was a crazy cold night so, on my way back, I decided to run to get back to my door faster. Plus, I was holding my foil-wrapped chili dog dinner and I didn’t want it to get cold. But the next thing I knew, a car with flashing lights screeched to a halt in front of me and someone with an authoritative voice ordered to get on the ground.
I had to spend the next couple of minutes explaining to the New Jersey PD why I was running out of a convenience store at night in a "ski mask" while waving a shiny metal object.
3. I Was Just Trying To Make A Point!
This happened to me in the fourth grade. All of the kids in my class had figured out that they could get up whenever they wanted if they said that they had to sharpen their pencils. I guess it was a way to break up the monotony of the school day. Obviously, a lot of students took advantage of that privilege but I didn't want to be one of them.
Mrs. Spangler, our teacher, had clued in to students lying about having to sharpen their pencils and started cracking down on it. During an assignment, my pencil actually got dull to the point that the wood was scratching the paper. I decided to use my nail to chip the wood away from the graphite instead of risking a trip to the sharpener.
As I was doing that, Mrs. Spangler just so happened to walk by and exclaimed, "You're trying to break your pencil!" I didn't have time to establish a defense before she admonished me in front of the whole class. I still think about it sometimes…I'm 37 now.
4. Oh, Brother, Where For Art Thou?
My sister came home one day to find her boyfriend in an awkward position with our brother. Her boyfriend was holding our brother’s head in his lap and stroking his head as if to soothe him. Needless to say, my sister was horrified. She was just about to open her mouth and ask what the heck was going on when her boyfriend shushed her.
He turned around and whispered, "Oh, hey, be quiet. He just fell asleep". Apparently, our brother got food poisoning and was throwing up constantly. Her boyfriend showed up to return some things she left at his house. So being the good guy that he was, he helped our brother get some medicine from the store, change, and stroked his head on the couch until he fell asleep.
We laugh about it now but it was a really suspect situation.
5. Picture This!
I worked at a school portrait company. I retouched thousands of images and sometimes, as I’m sure you can imagine, I had to retouch some inappropriate things. High school kids get away with way too much. Anyway, I was retouching this high school girl’s portrait because what she was wearing didn’t photograph too well.
The shirt she was wearing became see-through under the camera lights and I had to retouch the picture to, well, cover her up. I was in the office by myself as a 20-something-year-old man editing this teenage girl’s portrait. Just then, a girl walked in and saw me as I was zoomed-in on this high school girl’s see-through shirt.
I was, "No wait! I can explain!" I told her that I wasn’t a creep and that I was just retouching the image to preserve this girl’s privacy. It was very awkward but since she worked as a photographer she completely understood once I explained. Thank goodness.
6. Bra-zen Behavior
This happened to me in high school. It was shortly after I started dating my first "boyfriend". At the time, I would often wear a camisole with a built-in bra layered under a V-neck tee. One day, I was wearing this outfit but wanted to go shopping after school for other shirts, so I brought a regular bra with me to try stuff on.
After I got out of the store, I, for some reason, didn’t want to put my bra in my bag. So, I put it in the armrest compartment between the front seats of my dad’s car and, of course, immediately forgot it was there. The next day, my parents were getting ready to go somewhere and got my little surprise gift—unintended as it was.
They had left the house but moments later my mom barged back in demanding to know why I was taking off my clothes in the car. I frantically tried to explain the clothes shopping story to her but to this day I’m not sure she bought it.
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7. We Were Studying, I Swear
Back in college my friend was giving out tours to potential students. He asked to show my room on a Saturday. I agreed and, being a college student, forget two minutes later. Now, back in college, almost all my friends were girls. I had a serious girlfriend from high school so I wasn’t trying to hook up or anything like other guys my age.
We used to sleep over in each other’s dorms and it wasn’t a big deal because they knew I wasn’t playing games. So, one night four of my female friends decided to sleep over at my place. Being a nice guy, I took the floor and let two of them use my bed while the other two got the good part of the floor. I got up at around 9 AM when they were all still sleeping.
So, I got on my computer in the same room. All of a sudden, I heard this key in the door. My stomach dropped—but I knew I was too late. In walks my tour buddy with four families! My two friends on the bed woke up and sat up in fear. They instinctively pulled the covers up so it looked like they were both in their birthday suits. Meanwhile, the other two on the floor were sleeping and I was on the computer just chilling.
Everyone looked at us in shock and I was just like, "Oh I forgot this was today". One of the dads laughed and said, "Well it looks like a nice school". All the guys on the tour looked like they were ready to sign up on the spot. I didn’t even try to explain anything, On the way out another one of the dads asked if the girls came with the room.
8. You Better Be Fishing For An Excuse
I was volunteering at a pool to get my instructor's certification. The girl I was with was really thirsty and asked if I would mind getting her a Powerade from the vending machine since she couldn't leave her class. She told me where her wallet was so I could get her change. Just as I was rooting through her wallet, another staff member walked in.
I was the most strait-laced, nervous kid on Earth so I explained the whole thing calmly. She either believed me or checked with the lifeguard later but, either way, the first girl got her Powerade and the pool hired me.
9. Boyband Bromances
This happened to me in my freshman year at college. Me and some of my friends got back to my dorm room from a party late and decided to keep it going in my room. Because this was a Catholic school, no girls were allowed on the men's floor of my building after midnight. It was kind of a bummer but it actually allowed us guys to form deeper friendships.
Anyhow, we were blasting NSYNC and drinking when we get a loud knock on the door. The RA came barging in and was all like, "Alright! The girls have to go!" But obviously, there were none in the room. He thought we were hiding them so he looked around. When he realized there weren't any girls around, he just laughed at us and left.
10. A Nosey Little Old Lady
My friend Anna was in her 20s but she looked really young. She could easily have passed for a minor. This one night, she had too much to drink and I had to carry her home on my shoulders as she was having a really hard time walking. As we got to her house, I went to let her down and she fell off and smacked her head on the fence.
She was wearing a skirt and as she fell it went up to her waist. I was trying to get her to wake up so she could go in her house when this old lady walked out on her porch and started screaming. "What are you doing to that little girl! Where are her clothes?" I tried to calmly explain the situation but that really wasn’t working.
The old lady started screaming louder and louder, "Where are her clothes? What have you done to her?" To make it worse, my friend wouldn’t wake up and I realized just how bad the situation must have looked. To calm the old lady down, I told her to call an ambulance. Just as I was about to phone the ambulance, my friend immediately came to and fixed her skirt and stood up.
The old lady was like, "Oh you were right. I guess she was clothed the whole time".
11. It’s An Art Project, I Swear
I was practicing anatomy for a drawing course I was taking. For those who don’t know, that basically means that I had to look up the human body…in all its birthday suit glory. It was no big deal to me at the time because it was for academic purposes. I was just trying to get an understanding of the human form down so I could draw it.
Anyway, this one weekend I was drawing and my dad just so happened to walk into my room to ask me something. At first, he was like, "What the heck?" and picked up one of my drawings. I was like, "Wait! I can explain!" but he just walked out laughing. He knew that I liked drawing.
12. I Just Wanted To Check My Messages
I got super high one night with my best friend and his girlfriend. They stayed at my house. My friend is a loud snorer so his girlfriend ended up sleeping on my couch. My best friend was in my guest room upstairs. At four in the morning, I woke up still feeling pretty high. For some reason I felt the need to check social media but couldn’t find my phone.
In my half-awake and high state, I thought it would be a good idea to check for my phone downstairs. Without realizing his girlfriend was on the couch, I reached down by a pillow to check for my phone. Of course, she woke up and I was standing there trying to explain why, at four in the morning, I was grabbing her face.
It could have been worse; I could have started looking for my whole between the couch cushions…that would have been awkward. I don’t think she believes my story even to this day. Oh, and my phone was in my pocket the whole time.
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13. It’s Me, Not You
In the beginning months of a relationship, I was staying over at my girlfriend’s apartment. We were in bed, and the only light in the room came from a bright lamp on her side of the bed. Now, in addition to being a bit sensitive to bright light, I had a lazy eye that made it hard to focus on things that were really close. Things like my girlfriend, at that particular moment.
So naturally, I asked, "Could you turn off the light? You’re really hard to look at". I don’t know which of us had the bigger look of horror on our faces.
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14. Lost In Translation
When I was 17, my phone stopped receiving texts for some reason. I went online and told my boyfriend I wasn't able to receive his messages. I told my older sister and she said I could give her my SIM card and then she would see if it worked on her phone. So, I gave her my SIM and she said the texts were coming through fine.
She offered to forward my messages from her phone to mine. I can’t remember exactly what the process was but she had to open the messages first. The next words she said made my stomach drop: "Erm…this text will look weird when it comes through from me but just remember it's not from me. It’s from your boyfriend".
So, I got my SIM card back from her, went on my phone (which started working again), and read the text which had come through from my sister. It read: "I will take it off for you baby ;)". Now, my boyfriend and I never exchange dirty texts so I was confused and mortified when I read that message. I tried to figure out what it could have been.
Then I remembered, I had texted my boyfriend to say that I couldn't shower because there was a huge wasp on my bottle of shampoo and jokingly asked him to come over to take it off for me. By the time I remembered that, my sister already had a very different impression of me.
15. Sorry, Wrong Door
During lunch at my school everyone would be in the lunchroom. It was a small school so pretty much everyone ate at the same time. A friend of mine and I would skip lunch and spend the time just running around the school doing whatever we wanted. One day we were playing an extreme form of hide-and-seek all around the school and she ran into the bathroom.
I went into the bathroom after her and stepped up on the toilet seat and peeked over the stall divider. I had planned on being like, "Ha! Got you!" but I ended up being the one in for a surprise. My friend wasn’t in that stall! The girl assumed I was trying to be a creeper and went and told a teacher and everyone else that I tried to spy on her in the bathroom.
I had to sit through the whole, "Are you a lesbian?" talk from a very conservative teacher at a very country school.
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16. Just Casually Browsing
While my husband was in nursing school, he lived at home with his parents. He had an…unfortunate situation when he was studying anatomy. He had looked up something to do with the male genitalia, made his note, and continued on with his studying. But, without thinking, he left the browser open. His dad popped into the room just then.
Of course, his dad saw the screen and mumbled, "Oh, uh. Ok," and walked away while my husband yelled after him, "Wait! I can explain!" Both my husband and my mother-in-law are nurses so they have tons of situations that would be awkward for other people to walk into.
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17. Alexa, Turn Relationship Off
I was dating this girl once—let’s call her Alexa—for about a year. Everything was going well she was fun. Anyways, one Sunday night we got home from spending the weekend at the beach and she went home to see her family. I was playing video games and just relaxing at my place when an old girlfriend of mine—let’s call her Becky—called me.
Becky was a fun girl that I use to love very much but she had moved away for college. Anyways, Becky called me up out of the blue and said that she was back in town to meet her real father. Sidebar: this was something that neither I nor she knew about until that moment. Anyway, she said that the meet didn’t go well and she had nowhere to stay until her flight the next the morning.
Now, I didn't want things to get messy because I was happy with Alexa but I was also not the kind of dude that abandons someone they know in a time of need. So, I went to pick her up and asked her what she wanted to do. She said that she wanted to stay in the car and talk while she calmed down. After what she’d been through, I totally understood.
During all of this, I hadn’t really realized that we were sitting in the parking lot of a convenience store that was right next door to Alexa's place! And, of course, as fate would have it, Alexa got the urge for a late-night snack and went to the convenience store only to find me sitting there with an ex-girlfriend late at night.
I eventually managed to calm Alexa down and explain what was really happening but she had been cheated on before so she had trust issues. We stayed together for a while after that but I could tell she never really trusted me. A friend of mine said something like, "Don't do good things that look like bad things". So true. No good indeed goes unpunished.
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18. Entering But Not Breaking
I was out one night and forgot my keys. I thought that trying to climb through an open downstairs window would have been a good idea. Just then, I heard the sirens and saw a patrol vehicle pull up outside. Thankfully, my housemate woke up when he heard the siren and came down at just the right time to help me explain the situation. But…
Because we were renting at the time, the addresses on our IDs didn’t match so we had some more explaining to do. Also, a dog followed me home and they asked if it was my dog. It was cute so I said it was.
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19. Are You Cat Calling Me?
One of my friends was in a cycling accident commuting home from class one night and wound up in the ER. She needed someone to make sure her dog, Fox, was taken care of and asked me to do it. She explained to me that she left her bedroom window unlocked so I should be able to get in the house. Now, Fox was only semi-familiar with me and I didn’t like the idea of crawling in a window and facing a pretty big dog unannounced.
So, I got the window in the alley cracked and I was trying to call out to Fox and let her know that I was there and coming in. I was saying stuff like, "Hey Foxy girl. Foxy Lady, etc., etc". Meanwhile, the upstairs neighbor heard me while I was calling out and watched as I was lurking around the windows, peeping in.
Luckily, I was able to clear it all up pretty quickly.
20. Are You Smothering Someone?
This happened to me several years ago when I was still living at my parents’ place. I was dating this girl and we were sitting on the couch, watching a movie. She was prone to migraines and was having one at that moment so she laid her head in my lap. She asked me to turn off the lamp on the side table because it was making her migraine worse.
Then she said it was still too bright and asked if I could put a pillow over her head. So, we were sitting there in the dark, ostensibly watching this movie when out comes my dad from the bedroom. He looked just as shocked as I did until I explained the situation to him.
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21. Just A Happy Family
I was 18 or 19 when this happened to me. I was really close friends with a girl who had a little sister and her birthday was coming up. I can't remember how old the sister was but she was still in the "Chuck-E-Cheese" era and that's where she wanted to go. Her parents said no, but we took her anyway to make her happy. I didn't consider the image until we arrived.
My friend had fallen off her longboard a few days prior and had a pretty nasty black eye. Her little sister was in gymnastics and had injured her arm so it was in a sling. So, in we walk, looking like a very young couple with a child and both women were sporting fresh injuries while I was unscathed. The look on the hostess's face said it all.
I even felt like a monster despite not being responsible for any of it. I’m shocked no one called Child Services.
22. Brainstorming In Bed
My college best friend and I once went to hang out at my family camper. It was an RV that we kept at a local campground April through November every year. Anyway, we went there to work on a book idea together. We actually just goofed around and talked about music—basically, we always just talked about music back then.
We definitely didn’t accomplish anything book-related and just talked while sitting around on my parents’ bed. My dad was a bit taken aback when he visited the camper the next day to find messed-up bedsheets and no book…
23. The Sun Doesn’t Shine Down There
I suffered from left leg sciatica since I was about 14years old. For those who don’t know, it basically means that I used to get really, really bad pain in my leg. I’ve since had spinal surgery to correct the issue—but not before I had this one painful encounter. This happened to me in back when I was in high school.
I discovered that the only way to deal with a flare up of my sciatica was to have someone legit dig into my left bum cheek. It actually offered instant pain relief as the muscle calmed down and the nerve relaxed. Anyway, once in the eleventh grade, I had my girlfriend over to my parents’ house and we went downstairs to watch a movie.
While we obviously messed around down there all the time, that time was actually very innocent. I had a flare up when we were down there and she offered to "massage my cheek" to help with the pain. I laid across her lap face down while she went to town. It felt so good to not have my leg be on fire. Of course, that would be the exact moment that my dad walked downstairs.
In the dark, it appeared to me that my girlfriend had her hand, well, up my poop chute. He immediately screamed, "Whoa! Oh my God! I’m sorry!" and ran back upstairs. I had to go and explain what was actually happening. He still thinks she was…digging for nuggets. I’m almost 30 years old now.
24. Was I In-Tune, Officer?
I was driving back to college from my grandmother’s house one day. I was holding my hand up to my ear to hear myself better as I was practicing for a choral performance a couple of days from then. It must have looked to people outside of the car that I was yapping away on the phone because I got the wrong kind of audience.
A squad car pulled me over. When the officer walked up to my car window, he was surprised to see that I actually had my phone packed away in the back seat. He asked me what the heck I was doing if I wasn’t talking on the phone. I had to awkwardly explain that I was trying to hear myself sing better.
After a long stoic pause, I panicked and couldn’t think of anything else to say so I went, "Just try it!" and started singing. He let me off with a warning. I guess my singing still needed more work.
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25. Bumping Into Trouble
I was walking along one night with my wife and we bumped hips accidentally. I bumped her again in a playful way, she bumped me back harder and it escalated from there. For my final victory, I timed it just right to knock her into a lamppost so she fell over, laughing. But, I guess, not everyone found it very funny.
I heard a "whoop, whoop" and a squad car came up behind us. The officer must have only seen my final blow because he wasn’t laughing. My wife started laughing so hard at the absurdity of it all that tears were streaming down her face which only made it worse. The officer grabbed me to stop me from "attacking" my wife.
It took quite a while for my wife to stop laughing long enough to explain what had happened. Longer still for the officer to believe our story.
26. Papa, Please Don’t Preach
In high school, I borrowed my parents’ van to take my girlfriend on a date. We went out for dinner and then headed off to a friend's house for a bonfire. My girlfriend changed clothes in the van from her skirt and tights to sweatpants on the way over. She forgot her clothes in the van which definitely gave the wrong impression.
My dad pulled me aside the next day holding my girlfriend’s tights. I started saying, "It's not what it looks like, it’s not what it looks like," but my dad cut me off. He clearly didn’t believe me because he just went on, "I want to make sure you guys are being safe," and, "Don't worry. I won't tell your mother". I couldn’t get a word in after that to explain.
27. Capturing Memories…And Unwanted Attention
When I was visiting my hometown, I drove past my old childhood home where I'd grown up. I decided to take some photos of the house for nostalgia's sake. There were a few little kids playing out in the front. I thought, "Perfect, the house is still filled with children's laughter and all that good stuff". So, I took out my camera and, well, probably should have considered the optics.
Cue an angry bald man rushing out of the house screaming at me for taking photos of his kids. The kids started bawling their eyes out and I just drove away in a hurry without stopping to explain. I don’t even know how I would have tried to explain that one.
28. Red And Itchy And Guilty All Over
This didn’t happen to me. Thank goodness. Because I wouldn’t have been able to explain. Years ago, my manager was working in the office one weekend. He always had really bad eczema in different places all over his body. That day, his eczema flared up. As no one was around, he dropped his jeans and started going to town on the eczema on his thighs.
Just then, a cleaning lady walked in. She took one look at him and walked out again without saying a word. What makes it worse was that the following Monday, his manager wanted to speak to him about a completely unrelated "sensitive issue". He thought he was going to lose job.
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29. Um, I Think Your Toy Is On
When I was 16, my boyfriend’s (now husband’s) parents took me on a beach vacation with them. His dad was kind enough to carry my luggage to my room. When we got up there, his face turned bright red. I just thought that he was hot from the physical exertion. My boyfriend came in after and said, "So…my dad says your luggage is vibrating".
I had one of those handheld face washing devices that you put a little makeup remover pad on in my bag and it had turned on. His poor dad thought I had brought a naughty toy on the vacation. So, I actually had my boyfriend take it down and show his parents what it was so they wouldn’t think poorly of me. We all had a great laugh about it.
30. The Luck Of The Irish
When I was younger, my family and I were going on a trip to Ireland. My dad decided he didn't want to bring his entire jar of Metamucil on the trip so he put some in a Ziplock bag and put it in his carry-on. Of course, plastic bags aren’t very protective so the Metamucil got all smashed and crushed up on the flight.
When we arrived, it was fun trying to explain to customs that the small bag full of fine light brown powder they found was not actually what it looked like.
31. It’s Like Stealing Candy From A Paraplegic
I was in a relationship with a girl who was paraplegic and needed a wheelchair. We both loved cosplay and going to conventions. This one time, we made a funny cosplay of a character from Monster Museum. When we got to the convention, we went into a part of the venue that was empty to get a couple shots of just us. At the time we didn't know it was technically off limits.
So, I helped her out of the wheelchair and laid her down so she could get comfortable and I was wheeling her chair off to the side to be out of sight for the photos. I always messed around too much and I was pretending to run away with the wheelchair while taunting her. I did it all the time and it always made her laugh.
I think I said something like, "Good luck trying to leave without your wheels!" But before I could turn around to see where I was going, someone wrestled me to the ground. When the world stopped spinning, I realized that the convention center security had tackled me. They thought that I was harassing my girlfriend.
We cleared it up and they gave us both a slap on the wrist because we weren’t supposed to be in that area. The security guards also got in trouble because they were not supposed to touch people. I felt bad because their hearts were in the right place since they thought I was robbing a girl who couldn't walk.
32. You Had Something In Your Hair
I was at a concert years ago and some dude flicked his roach into the air when he was done with it. The cherry landed right on top of this girl's head and just started burning into her hair. I was standing right beside her so I just immediately swatted the burning ember from her hair. She turned around, along with her boyfriend, and they were both like, "What the heck, man?!"
I tried to explain that someone had thrown a roach into her hair but they really didn't seem to believe me. I guess they just thought I was some weirdo who liked to whack women on the top of their head or something. They just turned back around, visibly annoyed, and walked away. Then some guy behind me was like, "Nice job, bro. I watched the whole thing".
I was like, "Why didn’t you say something when they were questioning me?!" Anyways, no harm done but it was a funny story.
33. Well, That’s Just Tuba-Bad
This didn’t happen to me but to one of my friends from college. An officer pulled him over because he thought that my friend was using a crack pipe or something. That couldn’t have been further from the truth, however. My friend was a tuba player and was practicing lip slurs with his mouthpiece when the officer pulled him over.
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34. Aren’t You A Little Young To Be…
A few years ago, I went with my dad and my then baby sister—I was 17 at the time—to get a cake. We selected the cake we wanted and before we got up to the cashier, my dad asked me told my sister so he could pay. The cashier called my sister cute and said I looked good for someone that just had a child. I guess that she hadn’t seen us earlier, walking around the store.
Being the genius that I am, I laughed and explained that I was only 17. The cashier instantly went white and wide-eyed, assuming something you could guess about the relationship between my dad and I. At the time, he had a good amount of white hair so he looked fairly middle-aged in comparison to me.
Before I could say anything, the cashier was sort of stuttering asking if we were an "item". I finally managed to explain that he was my father and that the baby I was holding was not my daughter but my baby sister.
35. I Run A "Disposal" Business
Before I tell this story, you have to know that I’m Eastern European and have a thick accent. Anyway, this one day, I invited my friend out on a hike. When we got to the woods, I needed to get my water bottle from the trunk. I had had to move some painting supplies earlier so I made sure to line the trunk so it wouldn’t get paint everywhere.
When I opened the trunk, my friend’s face just dropped. It was the scared face when your tracksuit-wearing Eastern European friend opens a trunk lined with garbage bags and packed with rolls of plastic wrap and a hatchet in the middle of woods. I made it worse when I said, "Is no problem. Just had to move messy things. Do not worry".
I thought he was going to go running through the windows.
36. A Girl’s Gotta Eat
My dad helped me out by leasing a car for me. He wasn’t very tech-savvy so whenever I had to pay him back, transferring money into his account wasn’t really an option. I always paid him in cash for the car payment. We would meet up to have dinner in a restaurant and I would give just give him my car payment then. No biggie.
Well, this one time, I got to the restaurant early and had to go to the bathroom. After peeing, I went to wash my hands and decided to double check my money to make sure I had the right amount of cash. As I was counting the thick bundle of cash, a random guy walked into the bathroom, looked at me and then just ran out back out without saying anything.
I thought, "How embarrassing, for him, walking into the women’s restroom like that". He then proceeded to walk back in again and walked past me awkwardly. That’s when I saw the urinal! I realized that I was in the men’s room! Counting cash!
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37. For Training Purposes Only
This didn’t happen to me. I heard this story from a health and safety trainer I used to know. He went out on the road a lot, all up and down the country. One day, he was at a petrol station and went to grab something out of his boot. As he did, this two old people walked past him with worried looks on their faces. He didn’t think much of it and carried on his journey.
As he was going down the motorway, he noticed a squad car a few cars back but again thought nothing of it. Then another unmarked squad car swerved in front of him and the one further behind sped up to pull him over. He stopped, obviously thinking that he had been speeding or something and that the officers were maybe being overzealous.
But as soon as he pulled over, the officers jumped out of their cars and pulled him out of his car with their service arms pointed right at him. One of the officers went straight to the boot of the car opened it and then just burst out with laughter. Turns out, when that old couple walked past earlier they spotted the child training dummy and thought it was real, so they reported it.
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38. I Nailed It
I brought a hammer to the office to hang a whiteboard. I left it in my laptop bag and forgot to take it out when I got home. Days later, my boss came up behind me and asked, "Do we have a hammer in the office?" Without thinking, I reached into my bag and handed him the hammer while still looking at my computer screen.
A few seconds later, I realized my boss was still standing behind me. I turned around and he was just standing there staring at the hammer. He was like, "Seriously? You just carry a hammer with your laptop? Are you a psycho?" I didn’t say anything but in my head I was like, "Dude, you’re the one asking for the hammer".
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39. You Better Not Be Talking To Me
I live in a rough neighborhood in Brooklyn. A few weeks ago, I was walking my girlfriend’s small, black, three-legged dog late one night. There are a lot of guys that hang out by a busy corner drinking and blazing on their stoops. Anyway, one of them went to take a leak by a near their trash area near all of their garbage bins and stuff.
He was facing the building with his back to me. So, as he was relieving himself, Pepper (the dog) decided she was going to be stubborn and just sit down. I kept trying to get her to get up so we could go home. As I was calling her and telling her, "Come on. Come on, let’s go," the guy must have heard me. He looked up from his business and locked eyes with me through a mirror that was in the trash pile.
He was immediately hostile and was like, "Ey, yo! What you doin’!" He couldn't see the dog I was talking to because she was ten feet behind me in the shadows…and she was black. He must have thought I was trying to fight him or just some creeper who was watching him take a leak. Obviously, that was not at all the case but good luck explaining.
As he was zipping up and turning around to confront me, Pepper hopped up and trotted by and broke all the tension. He was like, "Oh shoot, my bad! I didn't know you were talking to the dog". We laughed about it and carried on our separate ways. Stupid Pepper.
40. Hello, Darkness, My Old Friend
Back in the day, I was still living with my parents. I was watching a movie in my room with the lights off and just the TV on—got to make it cinematic. Anyway, the movie faded to black and the sound cut out for a tense scene transition. At that exact moment that my entire room was shrouded in darkness, my mom walked in to ask me about something.
To her it must have looked like I was just sitting there in the middle of my bed in the dark like a weirdo. Luckily, a few seconds later the movie resumed and she gleefully realized that I wasn't just being a loon.
41. Sir, Step Away From The Vehicle
Years ago, I was on the way back to a friend's apartment for an after-party. I had already been out that night out so I was a bit tipsy. Well, alright, I was a lot tipsy. As I was walking, I decided to get a CD out of my car which I had parked across the road. I opened the driver's door with the key and sat in the driver’s seat to stabilize myself.
I still had one leg outside the car and was barely holding the door open while I frantically searched for the disc in the center console. It should be noted that I had my right hand holding my keys resting on the top of the steering wheel. I couldn't find the CD I was looking for, so I looked up to call across to my friends going into the door of the apartment.
Just then, a squad car pulled up beside me It took me a lot longer than I was comfortable with trying to convince the three officers that I genuinely had no intention of driving off.
42. Laughter Is Contagious
I have a habit of laughing uncontrollably when I’m nervous or uncomfortable or in awkward situations. The more awkward the situation, the more I laugh. Anyhow, this one time in high school, I went up to a friend to ask him if I could borrow a book from him that I had been wanting to read. He said, "Oh, that book wasn't mine".
Apparently, he had borrowed it from a girl whose name he couldn’t remember because he was new and it was a common name. So, I pointed at the girl who I thought would be the one and asked, "That girl?" Just at that moment, she turned around and saw me pointing at her. I couldn't help but chuckle because I knew it looked rude that I was pointing at her while talking about her.
Realizing that from her point of view it looked like I was making fun of her, it made me laugh even harder which made the whole thing worse. Which made me laugh harder which made the whole thing worse and you get it. I don't know if she even got mad, I was laughing so hard that I was doubled-over at that point. In case you’re wondering, I never got the book.
43. What We Do In The Dark
I was working at the local grocery store when my friend went into the bathroom. I decided to try and scare him. My plan was to just open the door and turn off the lights but actually be waiting in there to spook him. So, I got in there and turned off the lights. It was perfect because I was wearing a black jacket with a hood.
Then the door opened and a customer turned on the lights and freaked out. He was like, "What the heck!" and then just turned and walked out. I guess my prank worked but not on the right person. He must have thought I was creep.
44. Is This Your Dirty Laundry?
My girlfriend came over to my apartment and found another girl’s underwear and driver's license on my bed. I'd just done the laundry, and apparently my neighbor had accidentally left some stuff in the dryer. I hadn’t seen it and tossed my clothes in on top of her stuff. Fortunately, my girlfriend believed my explanation because the whole pile of clothes was still warm from the dryer.
45. This Better Be Your Lacey Thong!
I had a good female friend in high-school named Natalie. I had a big crush on her and we ended up dating later but at the time of this story she was with someone else. Anyways, she came to my house to work on a project after school one day before my mom came home. She finished up and then had a date with her boyfriend so she needed to change.
Being the lovesick puppy dog that I was at the time—even though she was seeing another guy—I told her she could change in my room. She did and then left without incident. I was chilling downstairs later that evening and hadn’t gone back to my room when my mom got home and went upstairs. I don’t know why, but for some reason she decided to look in my room.
The next thing I heard was my mom shouting my full name, loudly and slowly the way she only did when I was in serious trouble. Confused, I ran upstairs to find my mom holding a lacy, see-through, blue thong. Apparently, it fell out of Natalie's bag when she was changing. The worst part was there was no way I could convince my very angry mom that nothing happened.
46. Lonely Nights At Sea
I was in the navy, stationed on an aircraft carrier. In the sleeping compartment I was assigned to, we had lockers called "coffin lockers". Our beds were on top of the coffin lid, which we opened the way you would think to get to our stuff. The beds were stacked three high, with not quite enough room to sit up while in bed.
We were on a deployment, so we brought whatever we couldn't live without. One of the things I had was a rechargeable shaver for my legs. Well, apparently when I closed my locker this one night before going to be, I'd jarred the battery cover and the shaver intermittently vibrated against the wall of the locker. However, I didn't realize what had happened at first.
I heard the vibration and assumed that the girl assigned to the bunk under mine was going to town on herself with a vibrating toy. It went on and on, so then I started thinking that it wasn't her with her toy—unless she had the stamina of a Spartan. I got out of bed and opened my locker and that’s when I realized that it was my shaver.
At that moment, the girl laying in her bunk below mine opened the curtains and gave me a look. I showed her the shaver, and explained what happened. We both had a laugh when she said that she thought I had been going to town on myself with a toy.
47. How Many Babies Do You Have?
My dad used to drive the ambulance for both my town and the neighboring town. He helped deliver the first baby in our town's ambulance after the mom started going into labor during the drive to the hospital. It was a big deal and even the local paper covered the story. We’re from a small town, alright. That’s big news where I’m from.
We ended up becoming great friends with the family and even went on a few family vacations together when I was growing up. Then my dad helped give birth to the first baby in the other town's ambulance and again got a fun little article in the newspaper about it. He becoming something of a local hero. It was pretty cool.
Anyway, the mother of the first baby that he had helped deliver in our town’s ambulance saw my parents in a packed restaurant one night. She ran up to my dad and shouted, excitedly, "You had another baby without me?!" My mom said the whole restaurant went totally quiet.
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48. Always Be Prepared
I was attending a corporate function years ago when I noticed that the president of the company was trying to clean his glasses with a paper napkin. Being the well-prepared person that I am, I always keep a microfiber cloth in my pocket. I wear glasses, too, and I prefer to actually clean the glasses, not just smudge the oils around. I digress.
So, I reached into my pocket, grabbed a cloth, and handed it to him. And he responded with a confused and suspicious sounding, "Huh". Now, at that time, I also had a son who was going through potty training so I tended to keep spare clothes with me. I usually kept them in my backpack but I also kept backups in the pockets of my overcoat.
After hearing his odd reply, I looked over and the president of my company was kind of staring at the (unused, thank God) pair of Jake and the Neverland Pirates underwear, boys’ size small, I had just handed him. Of course, my immediate response wasn't to laugh or to say, "Oh, those are my kid's backup pair". No, I had to go and make it awkward.
In my shock at handing the president of my company boys’ underwear to clean his glasses, all I could say was, "Those aren't mine!" I couldn’t have sounded guiltier if I had tried.
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49. The Dog Ate My…Oh, Never Mind
A female friend of mine—I’m a guy—who worked in law enforcement was on a welfare check once when the property owner’s dog bit her. She was about a mile from my house when it happened. Because I was working as an EMT, she decided to call me to see if I could inspect her wound and advise her on whether or not she had to go to the hospital.
She showed up at my house and limped into the kitchen. She told me that the dog bit her just below her left buttock, on the rear of her upper thigh. I was worried that the bite had might have broken the skin and that she would need to get it bandaged and possibly get a rabies shot. I told her that I would have to take a closer look at the bite to help her.
So, she took off her belt and pulled her pants down to around her knees. It didn't look too bad but there were two spots where the dog’s teeth had broken the skin. I told her I would bandage it up so she could make the 20-minute drive to the clinic. I was just about to bandage her leg up—then the worst happened: My wife walked through the door!
There I was with one of our female friends standing in our kitchen pants with her pants down. I was sitting behind her to get her bandaged up so her bum was in my face and my hands on her upper thigh. We both had the deer in the headlight stare as we realized how bad it must have looked to my wife. We then both shouted out in unison, "It was a dog bite!"
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50. With God As My Witness
I was really tall in junior high. One of my best friends at the time was pretty short and we had a running joke where he would put on a little kid’s voice whenever standing next to me because I was so much taller. Not everyone knew about our inside joke though. So, one day we were playing tag around my church building when things got awkward.
It was after most people had already left and my buddy ran into the bathroom and locked himself in a stall. Because I was taller than the wall of the stall, I pressed up against it and looked down at him and said in my best creepy voice, "You can't hide from me!" He used his little kid’s voice to reply, "Oh no! Somebody, please, help!"
Of course, that would have been exactly the wrong time for someone to overhear our little joke. One of the old church ladies was standing in the doorway behind us. I'll never forget the look of horror on her face. Turns out she was there to clean and caught us at exactly the wrong time.
51. Waist Deep In Trouble
In my freshman year of college, my roommate was a party animal, so I usually had the room to myself. However, he used Sundays to get his work done so he was constantly coming in and out of the dorm on Sundays. Anyway, this one Sunday, I clogged the toilet. Like…really bad. At the time, our plunger was this dinky little thing that definitely wasn’t "equal to the task". But that was just the start of the nightmare.
I was trying to plunge the toilet for like an hour without success. Finally, it looked like I made some progress so I tried to flush it again. Big mistake. The pipe in the toilet burst and started to flood the bathroom with unsettlingly brown water. I was barefoot at the time and in my haste to escape the wave of horror, slipped and bashed my head against the door.
The doors at my college were terribly cheap and made of this material that was essentially cardboard. So, when I slipped, I punched a hole in the door with my face and broke the lock, thrusting the door wide open. Just then, my roommate walked in, arms full of papers, to see me in stinky, brown toilet water and holding my bruised forehead.
It was every bit as bad as it looked. No need to explain that situation.
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