Kids say the darndest things, but it’s strangers that take the cake when it comes to providing messed-up personal stuff you didn’t want to hear and wish you never did. Whether you’re waiting for a bus, starting a new job, or on that awkward first date—oversharing can come out of nowhere, do its damage, and then stay with you forever. Let’s take a listen to these stories of oversharers who definitely crossed the line.
1. Tale Of The Tighty Whities
My mother is a legendary oversharer. One time I had to drag her away from a cash register—that’s her favorite place to corner someone and start telling them her life story. She was telling the cashier about her ex-husband, my father. Before I could stop her she was telling embarrassing intimate details about his sleeping habits.
She told this poor cashier that he would sleep with a T-shirt tucked into his tighty-whities and she never saw him fully naked in the 13 years they were married, because he would just untuck that T-shirt and roll the front of his undies down. Like, what are you doing Mom? I don’t even want to know about that, why would this cashier want to know that. What’s wrong with you??
2. A Flood Of Confession
I was seated next to a quiet kid on a high school band bus to a football game. He’d been in my band class for years, but I had never really spoken to him. He was the type who didn’t fit into anything at school that I ever saw. I resolved to get to know him a bit and open up a conversation since we were going to be sitting by each other for a few hours. I had no idea what I getting into.
It was like a dam burst; that dude talked for the whole trip. At one point, he told me that his mom was really unhappy with his stepdad but couldn’t afford to divorce him. And then he told me that his stepdad would drink too much and beat him with a stick, but he wasn’t sure if his mom was also getting beaten, and that scared him.
There was a brief pause before he said, “I never told anyone that before…” Then he changed the subject completely. I must’ve been 17 or so. It shook me. Like…obviously I was old enough to know that sort of thing happens, but too sheltered to think it happened to anyone I knew. I told my parents about it—seemed the right thing to do.
I don’t know what happened from there. He and I never really spoke of it again. I just looked him up on Facebook, though. Looks like he’s done really well for himself.
3. Two Family Tragedies
I was a 25-year-old female at the time and was at a hospital in the UK. I got discharged and was waiting for my taxi outside. This buff shirtless dude, covered in tattoos—they were decent too, in my opinion—comes over and asks for a light. I carry a Zippo for novelty so I obliged. We got to talking, and he told me something that blew me away.
He said he had just got out of prison after serving a life sentence for the murder of his father, but he’d only done it because his father had taken his baby sister’s life. He had his records on him and everything. He was at the hospital as he was diabetic and had experienced an issue of some sort after being released—I have no expertise here.
I have never feared and respected a man so much in my life. I bought him a pint after my taxi decided it wouldn’t be arriving. Decent bloke — we still speak nine years later.
4. Problems Afoot
I was buying crayons for my students at the very understaffed dollar store near my house. The sole employee in the whole store had to go out and help someone with the ice machine outside so I was waiting at the register for him to come back. Some other dude starts making small talk. He asks me why I’m buying so many packs of crayons.
I explain that I’m a teacher and you know, that’s just what teachers do because we get no budget. Dude looks at my flip-flopped feet and says, “Wow, if my teachers had feet like that I might have paid more attention in class.” Thankfully, the cashier came back right at that moment and I just bought my crayons and booked it out of there.
5. The Human Paper Shredder
I got a new co-worker on my full-time shift and on our second shift together she opened up to me about something weird. She’s addicted to eating paper. She has to eat some every day or else the urges get too bad. I now let her open new boxes of gloves so she can take the tab and have a little snack. Two shifts left to go with her. Get me out of here!
6. That Girl Just Gave Me PTSD
It was my first day at a waitressing job when I was 15 or 16 years old. One girl takes me out back for a smoke break and proceeds to tell me she’s pregnant (while taking a drag) and that the father could be any one of three chefs, but she’s decided it’s Johnny, because she likes him best and he’s her official boyfriend.
She then told me an elaborate story about how she got wasted at a BBQ in a park, went behind a hill to take a pee, lost her balance, and tumbled down the rest of the slope. She was somersaulting over and over peeing on herself in a great fountain arc as she forward rolled with her pants around her ankles. She said it was okay, because she was only a few months along at the time.
She kept going from there, telling me about how her thighs got chapped and she discovered that Sudocrem fixed that and also makes a great base for makeup and is good for your spots. Someone overheard this stream of consciousness story and got me out of the conversation because they thought I would quit on the spot. I had a shell-shocked look for the rest of the night. I don’t think I even got a word in apart from hello.
7. Not A Fan Of Fat
My first day at a new company and I was to meet another employee who would show me around the office. I met her in the lobby and on the elevator ride up to the office she proceeded to tell me how her husband has gained some weight and she is considering starting an office affair with a co-worker who is really into fitness and has muscles.
Here she made a gesture where she fanned herself while saying muscles. Like I had literally met this lady five minutes earlier for the first time in the lobby and she is already unloading all this stuff on me.
8. She Won’t Be Having Any Hot Flashes
My manager at my job when I was in high school decided to tell us about her attempt to take her own life on my very first day. She was like, “One day, I decided to take some pills and end it all. I grabbed a pill bottle out of my mom’s cabinet and took a handful without even looking at what it was and then lay down to die.” Of course, we were all like…what?
She continued her story: “I was so surprised to wake up in the morning perfectly fine. Confused, I checked the bottle to see what I had taken.” Yeah, it was estrogen.
9. World’s Longest Honeymoon Phase
My boyfriend and I stopped by his grandparent’s house to introduce me to them, but no one was home. My boyfriend had a key so we went right in to wait. After a little while, his grandfather comes home. He’s old and frail and almost deaf. He asks my boyfriend how we got into the house. My boyfriend reminded his grandfather that he had a key.
The old man then replies, “What if you came in when I was chiselin’ my wife?”
10. Verbal Diarrhea, And Then Just Diarrhea
My friend Karl, who’s a good guy, but hadn’t got much action yet, started a friends-with-benefits relationship with a 28-year-old, ferret-obsessed, clearly insane, total freak. Karl, my other friends, and I are all around 19 years old, so this proved to be a whole mess of odd and funny times. This is the context, now for the story.
So, Karl, two other buddies, and I were having breakfast at this local greasy-spoon that’s totally awesome. She comes in; we all, except Karl of course, ignore her, ’cause she’s totally lobotomized. She starts talking aloud about the usual garbage that pours from her mind to Karl: saving ferrets is her prime directive, how it’s fascinating that there was so much meat at a breakfast place, and stupid things she used to do when she was a kid.
It was at this time she remembered, quite casually, the time she had a bad case of diarrhea when she was a kid, and how she spread it on the walls of her bedroom. You could imagine what happened next.
11. Ground Floor Room Please
I was doing my practicum in a hospital and they brought a young man into the neuro clinic. This was my first patient. He was around 30 years old and he had fallen from a tree while working. He turned out to have a complicated neurological condition that had nothing to do with his fall. He was also diagnosed with severe depression.
He was in the hospital for months and no one ever visited him. The only time he felt a bit better was when I visited him and did some tests on him. He said, “It’s nice when you come and make me play with the colored toys and make me draw things.” One day he was looking out the window when I came in. He actually looked kind of peaceful.
But I had definitely misread his expression. He looked me dead in the eye and told me, “You know, if these windows didn’t have protective bars, I’d jump right out”. It was the first time I’d heard such a thing, and I’ve remembered it ever since.
12. Four Wheels, One Ball
I work at a big company in a huge industrial park and I had to walk from one end to the other at the end of a shift once. This was because I got moved halfway through the day. It was super hot that day and a dude in his car slowed down and offered me a lift, so of course, I hopped in. Three sentences later and I’ve already found out that the dude’s missing a testicle.
13. Not Her First Rodeo
During the training period at a new call center gig, one of my new coworkers got on the subject of how she’d done time for fifth-degree assault, and the amount of time she spent in prison was because the prosecutor had it out for her. Without thinking, as I have no filter, I blurted out, “There’s no way you’d get that kind of sentence for that without priors.”
My co-worker’s response, sounding defeated: “Yeah.”
14. Escape Room Van
When I was 17, I was training with a woman for a job as a courier. We were in a van, on the highway, and there was a lot of traffic. Basically, I slowly realized that I was stuck with her in this vehicle and I had no way out—and she seemed to be well aware of this fact. So that’s when she started sharing a bunch of personal stuff.
She began telling me about how it was in the bedroom with her 71-year-old husband, I think she was in her late forties. But that’s not the worst part. Then she told me about the time her uterus fell out while she was on the toilet, and she had to push it back in. I was like, please let another car hit us right now!
15. Trained To Overshare
I had to do a course and the trainer arrived, introduced himself to the small class of maybe four or five people, and asked a bit about each of us. He then told us his wife had passed on two years ago and he tried to take his own life. I felt horrible for him but he seemed genuinely happy with where his life was. I ended up staying back after class and having a drink with him at the bar.
He was a really cool guy. I hope he is still happy.
16. Train Wreck
I was working with a new girl one night, I literally didn’t even know her name. It was the most insane night of my life. She told me about every intimate experience of her life, that she wanted to try some sex act, but kept having flashbacks to her uncle taking advantage of her. She told me how her mom would invite guys over for a train when she was a teen and just a ton more stuff.
Bonus point, she turned me in to HR because when she told her fiancé that she told me all this, he freaked out, so she lied and told them I harassed her.
17. I’ve Got A Burning Question
I was riding a bus and minding my own business and some guy next to me went into a long elaborate story. After what seemed like ages, he finally told me about how he burned his house down. He said he did it for insurance money like three weeks prior. I wouldn’t have believed it…if his hands didn’t have massive burn scarring.
18. The Problem Is My Face
Apparently, I have a face that says “confess your darkest secrets to me.” In high school, I had a lab partner start off by saying she’s in a new foster home and she’ll be a great partner cause they basically let her do her own thing so she’ll always be available to study. Not knowing where this would go, I asked if that was different from her previous home.
You won’t believe what I got as a response. It was just an avalanche of horror including this gem: “At least this place didn’t watch me shower.” The only thing I could think of after was to ask if she was okay and if she needed me to say something to someone. She said no, it was okay now. She did turn out to be an excellent lab partner though.
In college, I had two girls tell me about their most traumatic experiences pretty close to meeting them. Those threw me for a loop and I had to ask my female friends if there was something I’m throwing out there that says I’m dangerous. They all said it’s the opposite. That I make people feel comfortable and that’s the reason what people overshare with me. But I still hadn’t reached my breaking point.
I had a co-worker ask me to help her submit some kind of entry into a radio station contest. I got to the part about her formerly working in adult films and escorting cause her daughter needed to eat. I had to tap out on that and suggested maybe she just come over and borrow my computer and submit this herself. I can only take so much.
19. Are You Sure This Is Part Of The Training?
So, I was temping at an office a few years ago and the trainer liked to talk about her personal life. She told me about her ex. She said that he was cheating on her, not just with one woman but many different women. I said that was terrible and I hoped the conversation would move on to another topic. Nope, she was just getting started.
She had many more stories about her ex-boyfriend. She told me that he’d filmed himself with the women. He then went on to stream the compilation of his conquests onto their TV. And then made her watch. I was stunned and not sure of what to say. Well, it didn’t end there. After a couple of minutes of me being quiet, she just continued with more stories about this jerk.
She said that a few days after Valentine’s day, he gave her a present. Sounds nice right? Not at all. He let her start unwrapping the present. In the box, there was layer after layer of tissue paper. And between each layer, there was a used condom that he’d used to shag the women in his compilation video. To say I sat there not knowing what to do is an understatement.
20. Super Friendly, Super Awkward
I was eating at a hotel restaurant and the server was super friendly. So, of course, I was friendly back. Why not? But then she started getting super personal. She told me about her ex-boyfriend. How he cheated on her while she was pregnant. She also told me she was getting clean from an addiction issue and that she’d terminated a pregnancy.
I was like…Can I have my chocolate milk now, please?
21. Tears Before Boarding
An old man asked me if I knew when the next bus would arrive and we ended up getting into a nice conversation that somehow led to the most heartbreaking thing I’ve ever heard. He told me about how his daughter was in an abusive relationship. He said the guy made her move far away from him and his family so they couldn’t help her. We were both crying by the time the bus arrived.
22. Sunshine, Lollipops, And Blackmail
This random girl started talking to me once. Everything was sunshine and lollipops until suddenly the conversation changed—and not for the better. She started going on about how she would plan a murder. Lots of details. Then she told me about how often she blackmails people. I promptly ended the conversation and haven’t talked to her since.
23. I’ll Have That Martini To Go
I met a woman while I was ordering a drink at a bar. She said she worked in child care. She told me all about how difficult it was working with traumatized boys and how she got too close to one and had inappropriate feelings. She showed me a picture and said anyone who meets him thinks he is really nice and not to judge him on his looks.
Then the barman came with my drink—and I immediately left. That was the entirety of the conversation with a VERY inebriated and probably terrible social worker.
24. Buh-Bye, Please Don’t Come Again
I was flying out of China and an ex-pat guy asked me for a smoke at the airport. Turns out he was being kicked out of the country. He was handcuffed and with armed guards. He told me it was because he was a medical student and he and his buddies had been stealing pharmaceuticals from the training hospital. No more med school for him.
25. He Turned His Life Around
I was training a new co-worker and this was our conversation on literally the first day I met him. He told me that he’d walked out on his wife and kids 30 years ago because he had a raging drinking problem. He said that now he had turned his life around, reconnected with one of his adult sons, and was now very actively a part of his grandson’s life.
He talked about his grandson constantly every single day. His other son refused contact with him, but he understood the reasoning and didn’t fault him for it. He was such a nice guy.
26. Not A Fan
I was buying some brewskis at a gas station and it was a Sunday during football season. I’m a big Dallas Cowboys fan so, as you might expect, I was rocking my Romo jersey. The lady at the counter looked at my jersey and remarked that I was a Cowboys fan. I said that yes, they disappoint me often, but I love them anyway.
Her response? “Ugh. I hate the Cowboys. My dad was a fan and he abused me.” Ouch.
27. I’ll Need A Shower After That Shower
I was once in a hostel in Southeast Asia, and there were four of us at the table: a teenaged English guy, a quite cool 35-year-old American guy, and a 26-year-old English girl. We found a deck of cards, started playing a drinking game, and by a certain point, we were all pretty inebriated. For some reason, we start talking about comedians and skits.
So I told this crazy and rather disgusting story about a skit I saw that involved golden showers and people being defecated on. At the end of the story, they all giggled, with the exception of the English girl, who said, “Well, some people like that”. Silence fell at the table. Nobody said anything for five endless seconds.
Someone eventually said something off that topic and the conversation resumed like before. We kept playing for a few more hours, and at some point, at about 5 am, the game ended and we scattered around the hostel. I was pretty wasted at that point, so I walked up to the girl and with my straightest face I asked her about it.
I apologized for the stupid question but I asked her if she was serious before when she made that comment. She didn’t flinch, and straight-up gave the most chilling reply she could have given. She said, “Well, I actually think that golden showers are one of the most amazing things in the world.” I do not recall what I replied to that, my synapses probably disconnected.
28. Mom’s Not Mum
My mother was an AVID oversharer. It wasn’t until I was older that I started to realize just how uncomfortable she would make people. There’s a lot of stuff she would pass off as normal, or even joke about, that was really weird. I made a new friend and she came over with her mother. My mother spent the entire time telling her mom about how I was “maybe” abused but she “wasn’t sure” and then shared her own experiences in the bedroom.
Within a week of moving here, my husband had learned about how she’d lost her virginity and how I was probably harmed as a kid—but who knows? Also about my brother’s intimate life, and how things aren’t great for him and his wife in the bedroom. And just so many more things that he really didn’t need to know.
29. The Ice Breaker Broke Her
The first day at my previous job, we did those dreadful icebreakers going around answering the “Tell me your name, where you’re from, and a fact about yourself” questions. The girl I sat next to said her name and where she lived, but I zoned out because it was legit 30 people in my training class and I had already shared my details.
But then suddenly I zoned back into reality because she was sobbing. She started telling the class—mind you, it’s the first day and not even two hours in—that her mom had to get custody of her daughter because she tried taking her own life and had to go into rehab. There was a bunch of other stuff too. The training was 11 weeks. So, that’s what she was known for.
30. Brain Wash Please
My ex-mother-in-law was an over-sharer to a disturbing degree. She told me about her yeast infection she had because she didn’t wash her hands before using a tampon. About the insecurity of her oldest son, because of the size of his package. She asked me what he should do as a 30-year-old virgin. If he should train first with a “lady of the night,” or use his co-worker who had a crush on him.
She “accidentally” showed me pics of her boyfriend on her phone and told me about her wiggling his thing while listening to music. I wish I could just burn those memories out of my brain.
31. I’m Gonna Need The Name Of This Park
I used to work at an animal shelter and we had several people who would come volunteer to help out. One of the women who came there on a regular basis went to lunch with me. She was such a sweet woman, a little older than I was at the time. She proceeded to tell me that she used to go to the park and hook up with old men because she felt sorry for them.
32. Unwanted Pics
I met an old friend’s girlfriend one day. Well, he was hardly a friend—more of like a friend of a friend. We hung out that day and his girlfriend was with us. That night, she randomly sent me naked pics and said that her boyfriend wanted to have a threesome with me and her. I kindly declined. If they asked me today, I’d hop on that faster than a frog onto a Lily pad.
33. I Know Your Evil Thoughts
I had a (God-fearing, apparently) stranger go off at me in this bizarrely specific rant about how deep down, I’m well aware of the evil thoughts I’ve had and deeds I’ve committed, and that I’ve been reveling in darkness and there will be a reckoning, etc., etc. To be honest, I didn’t even read it all, it was pretty unhinged.
I don’t know if he felt “doing God’s work” meant to randomly accost passers-by with hopeful admonitions on the grounds he might spook the occasional punter straight. Either way, it was somewhat unsettling.
34. Dating Tactic Number 14: Oversharing
I was on a first date once and before the night was through, this guy had told me a whole bunch of stuff. He told me about ending his engagement because his fiancée cheated on him at a party, and then he opened up about his history of emotional traumas. Well, plot twist. Somehow, that didn’t scare me off, and we’ve been married for four years now.
35. She Was Off Her Meds
My job was working at the cash register at my local pharmacy. This woman comes up to the desk and she’s picking her prescription. So, I go fetch her medication and start ringing her up. I’m usually pretty friendly so I do the usual small talk like, “How are you, how is your day?” Then, this woman proceeds to go on this crazy and unexpected rant.
She tells me about how she just found out her 14-year-old daughter was taken advantage of by this much older man and now they have to go to court, yadda yadda. Meanwhile, I looked shocked and mumbled something along the lines of, “Oh…I’m so sorry.” I finished the transaction and she left. My coworkers were all within earshot, and they all couldn’t believe she just randomly shared that.
36. Red Flag, Dead Frog
In high school, I once briefly met this odd dude. He said that he wanted to join me and my friend’s gaming club. Once we said yes, he then proceeded to brag about all the keyboards he’d broken over his knee. This should have been a major red flag, but I originally let it go as he was trying to act tough to impress us.
The next time I saw him, he stopped me in the hall and proceeded to tell me in great detail about this frog dissection he’d done and how much he enjoyed cutting the frog open. Mind you, I’d only met him twice at that point. His behavior was kind of scaring me. Needless to say, I got out of there fast and avoided him for the rest of the year.
37. Addiction To Myth?
In high school, I met a boy in mythology class that I found cute. I’m shy, so I never really talked to him until one day we were paired for a group project. Within fifteen minutes, he shared that he had been struggling with addiction. Me, being a completely innocent nerd, responded: “Cool. Uh, anyway I think the answer to number five is Patrocles.” I hate myself.
38. Cool Kid, Hot Trouble
In my senior year, there was this cool kid—I was pretty much a nobody—who came up to me and overshared that he was going to rob a local gas station. I laughed uncomfortably, and he said, “Nah, just messing with ya. But me and the boys are gonna get together and party. Wanna come?” Well, long story short. We did end up actually robbing a gas station. I drove the getaway car—and that’s not all.
This guy went to prison and never ratted me out for driving that night. I later married his sister (we’re divorced now) and she still, to this day, doesn’t know. She and I would go visit him in prison. He never told and she never knew.
39. His Mom Was Crabby
My mother was a huge oversharer who couldn’t keep her mouth shut. I heard her tell people how pot made her an easy lay. The number of times she had crabs. And that she’s a size queen. I just never could get it through my mother’s head that people—and especially her son—really didn’t need to know the sordid details of her personal life.
40. Dad Picked Up The Tab
When I was a freshman in college, I met a dude who told me a little too much about his personal life way too soon upon meeting him. It started with relationship problems. He told me how he couldn’t really talk with women. Then he said that he thought women were mainly for “reproducing.” Basically, he was just giving off bad vibes.
I don’t know if this is considered the most messed-up thing, but one week in class, without warning mind you, he told me something even more shocking. He said that he’d lost his virginity to a “lady of the evening.” And then the real shocker: THAT THE WOMAN WAS PAID FOR BY HIS DAD. By the next day, I was sitting in a new spot.
41. To The Moon! Or At Least Through The Window
I’m a cop and I once met a guy who was dying to tell me what he’d done to end up in prison. I had to go to a bail hostel for guys just out of the slammer because, ironically, it had been burgled. He was in the lounge and said hello. Even when I was a CSI in law enforcement, I liked to be pleasant. Big mistake. He took it as an invitation to talk. And here is basically what he told me.
He started out by saying something like how I wouldn’t talk to him if he knew why he was inside. He was talking like a ten-year-old with a brilliant secret. So then he was desperately trying to get me to ask him what he’d done to end up at the hostel. I wasn’t biting, cause I knew he really wanted to shock me or whatever.
Finally, he just blurted it out: “I took advantage of my two granddaughters.” I couldn’t help but look shocked. And he was like: “See? I told you that you wouldn’t like what I’d done. They were six and eight.” He went on to say that he did the right thing because he confessed rather than making them give evidence. Like he’d done this great and kind thing.
At this point, I fancied the idea of sending him out the window but resisted the temptation. These types of creeps have nothing left apart from memories and the idea that their stories bring some sort of status. The stories are currency, so I wasn’t going to let him think he was special. I still think of him. I like to imagine him in pain, with nobody by his side.
42. Sorry Wasn’t Enough
Not directly to me, but to my female colleague who I was standing next to. This guy came in and started telling her that he was suspended from his job for harassing a woman at work. He then openly admitted to doing it but said it was fine because he said sorry and couldn’t understand why he wasn’t allowed back to work.
I had to step in as my colleague was understandably pretty freaked out.
43. She Needs Noise-Canceling Headphones
I work as the receptionist in a medical office. So I’m not medically trained to give any advice or diagnosis. People will tell me their entire life stories, all the bad things going on in their life, what hurts today and so much more. One man went and told me all of his struggles with his addict daughter and how she was currently in rehab.
I had another lady ask me to look at her rash and ask if she should see a doctor. Another woman went in detail on how her father was a horribly abusive man but she still forgave him.
I really just want them to fill out their forms and give me their copayments.
44. I Hope The Kebab Was Worth It
I was waiting for my kebab whilst heavily pregnant and a young woman piped up and told me she was glad she got her period yesterday. Okay, that’s interesting. She then said that last night her mom and her dealer had come over. Together they’d helped her shoot into her neck for the first time. I was hoping for my kebab to appear, but she just kept going.
She then showed me her neck by pulling down her turtleneck and said she had only just stopped vomiting black and came to get something to eat. Needless to say, I was shocked.
45. First Date Oversharer
I went on a date with a guy and he ended up extending it by four hours just by chatting. It went from, “So, what do you like most about your job?” to “Oooh, let’s see what our top five kinks are!” It was crazy but we had a really cool connection after that. The date continued after we parted, with lots of very personal shared texts.
Long story short: he’s my fiancé now. I kept my previous phone just to savor those first few months’ worth of texts…and maybe those results.
46. I Hope He Meant Science And Math
It was the first night at my first base and I was right out of tech school in the United States Air Force. So this guy comes right up to me and introduces himself. He tells me his name is Mike. Seems like a nice enough guy. Then he says: “I’m heavily into S&M!” Yikes! The problem was I still had to share a room with him for a few nights.
47. Unpaid Therapist
No clue what it is about my face, but I have all kinds of people just walk up to me and tell me all of the most messed-up stuff from their lives. Since I have nothing better to do, most of the time I end up just listening for like an hour or two. It used to make me feel awkward, but ever since I realized literally everyone in this world just needs someone to listen to them, I became fine with it.
One time though, this random girl sat down at a table in a Chick-fil-a with me, and after about five minutes of chatting, she started crying and telling me all about her mental illnesses, suicide attempts, horrible family, and whatnot. I ended up just kind of sitting there with my arm around her for about half an hour while she cried it out.
Never saw her again, and I kind of wish there was more I could do, but she was already going to a therapist and everything. So I just gave her a really big hug.
48. Grad Bash Bashed By God
I was asked to take a guy’s picture with his friend at Universal Orlando during my grad bash. He never gave me his name. After I gave him his phone back, he looked at me and asked, “Do you believe in God?” I was a bit thrown off. I’m religious myself, but I don’t bring it up at school, work, and especially not out at an amusement park.
I told him that I believed. He then went on to tell me his life story about how he was super close to taking his own life until he found religion. I honestly just wanted to leave and go to the next ride with my friends, who were in the bathroom at the time. Once they came out, I bade the strange fellow farewell and I never saw him again.
49. A Truly Three Dimensional Character
Working in emergency services, you don’t always have the same partner so you tend to meet a lot of new people especially at a large company or department. One such time I got paired up with a random dude that I learned far too much about. I didn’t even have a chance to learn his name yet, when he was telling me about his hopes and dreams.
Seems he wanted to work at a rural fire department so he didn’t have to run as many calls and could spend his time working on his real passion: making 3D anime adult videos. Apparently, the market is under-saturated and it is his dream to produce such videos. This conversation lasted about two hours and I said maybe three words. I got “sick” that day and had to go home.
50. From Zero To Tragic In Sixty Seconds
People who are practically strangers have a tendency to open up about their trauma to me. It’s always out of nowhere too. The conversation could be about something completely normal and then they’ll be like, “I was abused by my dad and my brother took advantage of me every night.” And I freeze up because I had no warning and have no idea how to process that.
So all I manage to say is, “That’s messed up.” It still happens to this day because when I got a job, I knew something traumatic about all of my coworkers. It’s happened so much that when I meet people, I genuinely expect them to hit me with their tragic backstory within the first hour of knowing them. I hate it.
51. It’s A “Minor” Problem
My boss at the time made the mistake of hiring an older woman who was re-entering the workforce. He wanted to fire her the first day because she couldn’t even complete the basic hiring paperwork, which takes maybe 20 minutes for the slowest readers, in eight hours. He quickly lost his patience training her so he pawned her off on me.
Before the end of the first day, I was training her and she simply failed to learn anything that I explained to her. Also, she cried and called me mean for trying to “train her too quickly.” So then she reported me to the boss and she wanted to report me to human resources for creating—get this—a hostile environment.
I was actually out of town when she was complaining to my boss, but he managed to spook her enough by asking if we should just call this hiring a mistake and have her and the company mutually part ways. She straightened up pretty quick apparently. When I came back a few days later she was better and more eager to learn. Well, the nightmare was actually just beginning.
As we are leaving for the day, her husband is waiting for her in the parking lot with her teenage son in the back seat. I pull out in my car after they do and the entire time, her son is turned around in the backseat smiling at me through the rear windshield. The following day she tells me her son has a huge crush on me now.
Apparently, her teenage son thinks I’m so hot that he’s going along for the ride tonight so he can see me again. Then this crazy woman, who I have known for literally three days, tells me all of her teenage minor child’s physical stats—including how well-endowed he is. How the heck his mother knows this, I do not wish to know.
I actually had to remind this woman that I was more than a decade older than her minor child. This made her laugh and said he’d be older soon enough. She did not end up working with us for long.
52. This Was A Close Shave
On a first date with a girl, she leaned in and whispered something so disturbing, it’s unforgettable. She tells me, “I was with two guys last night. Obviously consecutively, not at the same time, I’m not easy.” After that, we had a nice, perfectly normal conversation until she had a couple of drinks. At that point, she leaned back in and said, “I’m completely shaved, do you want to see?” and promptly lifted her skirt to show it.
When she did, she said, “I never wear underwear, they get in the way.” After I talked to a few friends, including the one who set us up, they all said that she was desperate to be the center of attention and slightly crazy. You don’t say.
53. This Story Has Spice, Gurl!
I met this dude in college when he moved into the dorm. He was a goofy-looking redneck kid from the San Antonio area. I’m getting to know him when I notice his Spice Girls CD—this was like 2003—and I commented on it. He then goes into this long story of how he was at the Walmart in San Antonio, looking at the CDs in that store, and just happened to have bumped into Ginger Spice.
He goes on to tell me that Ginger Spice invited him into the tour bus that no one had noticed, and he lost his virginity to all the Spice Girls at once. My thought was: “Thank you for this story, I know instantly that I can never trust or believe anything you ever tell me again.” It’s been almost 20 years and I still can’t believe that was something he said in the first five minutes of meeting me.
54. Hi, My Life Sucks
I took out a client for a business lunch at a local small-town restaurant. I asked the waitress how she is—just to be polite. She proceeds to go on a five-minute spiel about how terrible her ex-husband is and how he’s ruining her life and how she feels terrible because of it. She finishes her rant, takes our order, and leaves.
The client then remarks that I must know her pretty well. I tell him the truth. That I only know her well enough to say hi in passing. My client looks at me strangely. “Oh, so then that was just as awkward for you as it was for me then?” “Yes, yes it was.”
55. Put The Pedal To The Medal
I once picked up a hitchhiker on my way home from an early Sunday shift. He’d been out drinking the night before. I asked how it went. I expected an interesting answer, but nothing this deranged. He says, “It went okay until someone stuck a knife in me.” Then he showed me the base of his thumb with a quarter-sized piece of flesh hanging off, covered in dried blood. I put my foot down hard as soon as he got out.