Some things are better left unsaid, especially when it comes to chatting with strangers. Small talk is fine, but things can get pretty overwhelming if people overshare too much about their personal lives with again, COMPLETE strangers. But unfortunately, some people haven’t gotten that memo yet. These people shares stories of when conversations with strangers went a tad off-topic. Content has been edited for clarity purposes.
Since When Was Being 27 Too Old?
“I was in a bar in Tokyo, Japan, and another foreigner started chatting me up. There were a few girls who we talked to but nothing was really happening.
He had some suggestions for other places to drink so we took a train up to Shibuya.
On the way he decided, unprompted, to let me know the girl at the last bar ‘said she was 23, but was probably lying’ which made me internally freak out and happy we got out of there. But then he followed up with. ‘Yeah, she was probably 27 or so which is way too old for me.’
Setting the stage, this guy wasn’t Japanese and looked 30ish, balding, and with a gut. He spoke fluent Japanese so he was super confident chatting up random girls.
I asked, ‘Why is 27 too old? Aren’t you older than her? Right?’
He followed up with, ‘Yeah, I usually try to meet girls in their early 20s. The younger, the better.’
I didn’t even answer. Just got myself lost in the crowd once we got off the train at Shibuya station and never saw the guy again.”
He Was A Wanted Man
“Thirty years ago, I was working in Seychelles Island as a consular officer.
One day this guy came in, I read him as just a boat bum with his ruffled hair, deep tan, and oft-mended sailors’ shorts. And so he was, a boat bum, sailing around the world on a pittance in a rough little sailboat.
I invited him into my office (this was pre-9/11, security was more relaxed) and offered him coffee. Then I asked what I could do for him. He warmed up by telling me he’d left Los Angeles a year and a half ago, sailing slowly across the Pacific Ocean.
‘So what can I do for you, sir?’ I asked.
He replied, ‘I needed to introduce myself to you. Somebody is trying to kill me and if it happens, you will immediately know who did it. Because I will tell you right now.’
It turns out he was in Tahiti at some anchorage where he met an American couple there. It was an older guy, and a younger, ‘cute’ lady. He soon learned she was the girlfriend. So they fraternized there, and then he sailed on. When he got to another island in Polynesia, he ran into the couple again.
One night, the man decided to bring over a special bottle for everyone to drink. Soon everyone got pretty hammered and they started talking about life, how they got into sailing, etc. At some point, the older guy went below deck and the girlfriend started telling him how they really got to achieve their dream of sailing to Bora Bora.
The older guy had been a businessman in San Francisco. He’d bought their boat with a boat partner.
The man said, ‘Way more boat than he could afford, but with a boat partner, you get twice the boat, right?’
Apparently, the older guy and his boar partner were friends, in the same circles in San Francisco. So once they got the boat, the older guy convinced his boat partner that he intended to sail to Alaska, so they tricked it out for bluewater cruising, spending almost a year doing this.
Then one day the boat was all ready, and it was the old guy’s turn to take the boat for a week out into the Pacific. So he dumped his wife, picked up his girlfriend, loaded a ton of provisions up, and set sail for the Galapagos Islands. So basically, he just stole half of his boat partner’s sailboat.
At this point, the older guy had come back on deck and was ticked off that his girlfriend had let the cat out of the bag. It was not immediately clear how furious he was, but as the night rolled on, the guy in my office in Seychelles realized the older dude was trying to steer him into thinking the girlfriend was joking. But then the man in my office started getting this weird vibe, ‘Like this guy was going to kill me.’
At first, they tried to turn it into a joke. The boat partner in San Francisco was rich, he wouldn’t miss the money. He’d collect insurance. They’d never find the boat, as the boat partner would peg him in the Pacific Northwest because he’d never discussed a circumnavigation. Then it got pretty dark. Pretty scary, in fact. And the guy in my office realized this was not a good situation. He knew too much and he was in the middle of nowhere with these people who have robbed a half-million-dollar boat and could easily make him disappear.
Long story short. He rowed back to his own boat and slept uneasily the rest of the night.
In the morning the formerly friendly vibe has gotten really ugly with the other couple. Not just ugly, but scary. The girlfriend looked super scared when they talked again. Invites continued, but they were really weird. He felt they were trying to get him wasted like they wanted to know if they could convince him to sail with them someplace isolated.
A wind came up in the afternoon when they were ashore. My man just sailed right out of the anchorage. And for the next six months as he sailed from Polynesia, then south and west, he found out they were chasing him through the islands. They chased him for a year, all the way through Indonesia and the Indian Ocean to Diego Garcia.
So in Seychelles, he visited me with a simple message. He gave me an envelope with the name of the couple. And he told me they’d been catching up with him. He’d heard through the grapevine they’d asked for him at Diego Garcia, a US navy base that tolerates sailors going through.
He didn’t trust ‘the authorities’ but he was willing to take a chance on me. If I didn’t get a postcard from Cape Town within sixty days, I was to assume he was murdered, contact his family, and report the name of the boat and his pursuers to the authorities.
About two months later, I got his postcard from South Africa. So I knew he survived. At least until Capetown.”
“I Don’t Know Why But I Invited Her On The Trip”
“I’m a female, and I met a girl at a local coffee joint. There were regulars coming there for months, so we chatted casually.
But one day I was going to drive to see friends three hours away for a fun-filled weekend. She said it sounded fun and I don’t know why but I invited her. She said yes and I picked her up the next day. Mind you, we were both around 19.
Well, it was a three-hour journey of hearing her life stories. She told me she was bulimic and used to hide jars of vomit under her bed from her parents so she wouldn’t get in trouble. She ran away and left them there. Then I heard about an Amtrak ride she took when running away that was three days long. She met an older couple there and spent the three days doing dope and doing other messed-up things with them.
She ended up getting pregnant by another guy at the coffee joint who she constantly told everyone how great he was. I never saw her after that.
Naive 19-year-old me just sat there driving and thinking, ‘Holy mole.’
I hope she’s ok now. Nineteen-year-old me had no idea how to support her.”
“She Needed To Record People Without Them Knowing”
“I worked in a catalog store and sold a middle-aged lady a dictaphone after she sheepishly asked me if there was something she could use to record people without them knowing. It was weird, but who am I to judge, I just worked the tills and suggested the items. However, she then decided to tell me she needed it because she was being bullied or harassed in her home. So she bought the dictaphone and I thought nothing of it.
On my next shift, she was back in and demanding to speak to me about the device.
The first words out of her mouth were, ‘Should there already be voices on it.’
I was kind of weirded out and surprised to hear that the device had already been used. But then she leaned across the counter and suddenly began telling me in more of a whisper tone that she was being attacked by spirits in her home and she needed proof. She played the dictaphone without being prompted to do so. Anyway, there was nothing ghostly on it, just some mundane household sounds and EastEnders (a British soap opera).
She became quite fond of me, came in repeatedly to tell me about the ghosts, but it just seemed so crazy that within like two shifts she had unloaded all her delusions. She even asked to know where I had gone after moving away. My old colleagues obviously didn’t tell her. She was a harmless lady, just a bit odd.”
Did His Co-Worker Just Admit To A Crime?
“I started to work with my coworker who kept falling asleep on me. On day two, I asked him if he was ok because he was constantly falling asleep.
He told me, ‘I have insomnia.’
Made sense, so ultimately I felt bad for the guy.
An hour went by, and he nodded off again. This was scary because he was a driver, so I yelled, ‘WAKE UP!’
He jolted awake and went back to driving, apologizing. Then he began telling me what happened and why he couldn’t sleep.
About 10 years ago he was going through a divorce, apparently, his daughter’s bedroom got broken into and she was beaten nearly to death at age 15. The assailant went to the mother’s bedroom and murdered her.
A couple of weeks later, they found the guy while he (the father) was taking care of his daughter. He was found murdered in a random town in a ditch. He went on to say the cops arrested him right away since he was the number one suspect, questioning him about the situation, to which he had no clue to what they were going on about. He had to get a lawyer and after a few days of questioning, they had to release him because they had no evidence that it was him.
His voice changed when he told me this and while he said, ‘He was a friend of the families, I wonder what happened to him. Guess we will never know but they got nothing on me.’
In a more menacing voice, after a long pause, it seemed like he caught himself and turned to me and said back in his original fun guy sweet voice, ‘But I wasn’t anywhere near so I don’t know how they did suspect me for it, but that’s why I have trouble sleeping every night for the last 10 years.’
I just got chills and thought to myself, ‘Holy smoke, you did it didn’t you?!'”
“Some Strange Canadian Greeting”
“I had to pick up a friend of a friend from her job before going to a party. I’d never met her before that night. When I got out of the car at her job site, she came out screaming and running towards me and jumped into my arms like we were long-time friends. This was in Canada, so I shrugged it off as some strange Canadian greeting.
We went back to the hotel suite to prep for the party with a few other people. We were drinking heavily and making small talk when I mention, ‘I gotta hop in the shower before the party starts’.
All of a sudden, she made a face and said, ‘Yup, I need one too, I’ll join you.’
Before I knew what was happening, she grabbed my arm and was pulling me to the bathroom. Keep in mind, this all happened in front of several people. They knew her, but I didn’t, so they were laughing. Apparently, she had a reputation of being a sort of crazy free-spirited person.
I was too wasted to think about what was happening and was kinda in shock. I didn’t know if she was weird or was coming on to me, but I did need to take a shower so I went along with it. Nothing happened in the shower, but later that night, we ended up running around Toronto singing and dancing. It was certainly the strangest interaction I’ve had with someone I just met.”
He Got More Than His Pictures Taken That Day
“I had to get my picture taken for a visa so I went to a local photography shop that took the pictures and printed them out for you right there. I had been talking to the guy as he worked on other people’s photos and when I finally got my picture taken he started opening up about his family.
Apparently, his son was killed three years ago in a car accident and he was telling me how much I reminded him of his son. I was going to school for engineering as a first-generation college student, etc. The son was killed in his senior year so he didn’t even get to graduate. He even showed me pictures, it was heartbreaking.
To make things worse he said he had a degenerative muscular disease and doctors had given him about two to three years before he’d be bedridden. He then went on to say his daughter was taking care of him and how she wasn’t married yet and deserved to live a young person’s life.
Man, it really put into perspective how bad some people have it. I still think about that guy to this day and hope he’s doing well.”
“Nice Big Smile And Soft Voice, But Utterly Insane”
“Sara was hired at my pub and had to be the most candidly messed up person I’ve met. On her very first shift, she came out and told everyone the toilet was clogged and someone had to go fix it because she had anxiety. We were like, ‘What the heck?!’
She kind of laughed and put her hand on her head and said, ‘This is so embarrassing, but I had kind of a big lunch and I didn’t realize the plumbing was so bad here. I don’t know anything about plumbing, or where the tools are and it’s pretty embarrassing so I think you should do it.’
Again, what the heck?!
I said, ‘Pardon me. Did you just… Oh. okay then.’
On her next shift, she began giving orders to other servers, to the bartender, and the support staff to do things. She had to be reminded of her own log-in code three times but felt the need to comment on how drinks should be made. And worse, she was wrong about half of her suggestions, so everyone was third-party embarrassed. No one wanted to correct her, because then you had to talk to her longer.
She reorganized parts of the restaurant nobody asked her to, and then complained about having to put it back when the manager asked her why she was disorganizing the restaurant on the clock?
She was straight-up rude with people on the phone, low-tippers, and even the owner. She was pretty and seemed normal enough until you spent time with her. She kind of looked like Ariana Grande when she was a Disney starlet. Nice big smile and soft voice, but utterly insane.
Imagine, on your second day at work telling the woman who’s been there 20 years that she’s not doing something correctly; balls of steel.
I asked if she wanted to stay for a drink after work, at which point she accepted and then walked out on the bill, which I covered. She told me she had to run, because she’d signed up for a Sugar Baby’s account and was meeting with a potential client and hoped this would work out because she was behind on rent. We were not on those kinds of friendly terms, we had probably talked about where she’d worked previously and her hometown and then Bam. More things nobody asked to know.
I just smiled and nodded, but the whole time I was just like, ‘What on Earth is wrong with that girl?’
On our next, and final shift together, I showed up to see she was eating two entire plates of food. Like, entrees. She may as well had dislocated her jaw like a trap door, thrown her head back, and dumped the plates in her mouth on how she was eating.
She was making a mess, and I was not cleaning up her mess again. So I just straight up asked her, not necessarily in my indoor voice why she was eating so much if she’d just told everyone she was going to throw it up again.
She laughed and said, ‘Oh, no, I’m fine.’
I was like, ‘Alright cool.’
She laughed some more. Then she brought up her Sugar Baby job and how she got some new clients and a new business model. She then went on into glorious detail about how lucrative it can be for a camgirl.
My old manager was a camgirl and made six figures in a year as an entirely average-looking girl so I don’t judge.
I said, ‘Alright that’s fine.’
But then she described, in all too graphic detail how many pounds she was projecting to gain per day and how folks were already sending her hundreds of dollars in tips for her to consume as much food as possible.
I later looked into this industry later on and realized she was right on the money (no pun intended) and there’s millions of dollars floating around out there for girls who get chubby in realtime.
I only spoke with her briefly and left. She got fired a couple of hours later for doing coke in the bathroom and making out with one of our regulars who’d just gotten married the day before, which I found out the next day.”
“Mind You, I’m A Guy Who Never Met Her Before”
“I was stuck driving a coworker out to a remote gas plant to do a system install. He was kinda weird but assumed he was just a socially awkward IT tech. Nope. He started telling me about him and his dad collecting World War l memorabilia and how proud he was of his German grandparents. I tried to make other small talks, but he would just trail off answering questions and start singing to himself. Thought for sure I’d end up on the news and a manhunt would be conducted.
Another time, I met the neighbor right after we moved in and she started telling me about them wanting another kid but doing the deed was hard because she was overweight and had bad knees and it just made it difficult.
Mind you, I’m a guy who never met her before and had my kids playing mere feet away so I could tell she was crazy.”
“Why Are You Here?”
“A customer explained to me the benefits of a coffee enema to heal everything from my acne to preventing cancer. I couldn’t get her to leave me alone for an hour because it was dead and no one was there to help. And thing was, I worked for a skincare counter in a department store. Like if you don’t need my products because of cleaning your skin with coffee, then why are you here?
But she went on about how she started her kids on these and did their enemas until they could do theirs on their own. What the heck?!
Then she also grabbed my hands and kept saying, ‘Promise me you’ll try it. Promise me.’ She finally left after I promised.
And no, I didn’t try it.”
“A friend of a friend of mine and I were sleeping on some couches after a party and we got to talking. More so her than me, I’m definitely a better listener than a talker.
She confided in me that she watched her fiance pull a weapon out and shot himself in front of her. She also told me how one day she and her best friend of years, someone I knew for a very short time, had been urban exploring on a smokestack catwalk in an abandoned paper mill. In just a blink of an eye, she watched her friend miss a step and fall to her death.
She wasn’t making these things up either, the next day I mentioned to our mutual friend that she had opened up to me about this stuff and he confirmed it was sadly true about the boyfriend committing suicide. The accidental death I had known about through the news, but I didn’t know she was the person with her though.
Poor girl witnessed the loss of two very important people to her and at the time she was only 19-20 when she told me this. I hope to talk to a near-stranger helped though, even if all I did was listen.”