If you’ve ever had a suspicion that someone in your life was keeping secrets, it’s likely that you eventually put that idea out of your head. You’re probably just being paranoid, right? There’s no way your wife is actually cheating! 

But when someone can’t seem to put their thoughts to rest, they might end up enlisting professional help to get to the bottom of whatever’s going on. And as you might expect, private investigators have some wild experiences while on the job. PIs have been opening up on Reddit about the craziest things they’ve uncovered, so we’ve gathered their most shocking stories below. Enjoy reading through these juicy tales, and be sure to upvote the ones that convince you that some secrets should probably just stay in the dark!

#1

A weird dad paid us thousand and thousands to watch his daughter during her first two years of college. Went to her tennis matches, friended her from various sock puppet accounts, ate at the restaurant she worked at, etc. Certainly not the strangest case or circumstances, but one where I’ve been tempted in the years since to reach out and let her know of the insane invasion of privacy.

Image credits: sock________puppet

#2

Most interesting case? A wife hired us to follow her husband, thinking he was cheating. He wasn’t.
Turns out, every weekend, he’d drive two hours away, check into a cheap motel, and spend the entire night dressed as a clown, performing birthday shows for terminally ill children at a local hospice.

He never told anyone. Didn’t want attention or praise — just said it made him “feel like a human again” after losing his own kid years ago.
Client was shocked. Divorce canceled. Marriage got stronger.

Some people hide affairs. Others hide their healing.

Image credits: Which_Algae1157

#3

Was hired to follow a woman who claimed she was completely blind (collecting insurance money of course). Spent the day following her around as she DROVE from store to store in a church van.

mcdave:
“Jesus take the wheel!”

Image credits: trackerjakker

#4

Someone wanted to know what their cat was up to when they were working. Paid me to tail it. I don’t like wasting my time but the works not always busy as a PI. Turns out the cat just walks around the streets, licks itself and climbs trees….

anon:
Day 17: This is the 4th mouse he’s caught. He doesn’t even f**king eat them. He just loves the thrill of the k**l.

Image credits: questionguy1000

#5

A mother hired me to look into the new boyfriend of her daughter who was way older than she was. She said there was just something off about him, and she was right. They broke up in the middle of the case so it got cut short and I never got to the bottom of everything, but he had like 5 different current addresses (some apartments and some private homes) all in different cities, and he had multiple cars registered in different states of which none of the plates were coming back as registered to him or a family member (in fact, one of his trucks was registered to a dead couple he had no affiliation with).

Also ran a vehicle sighting report and one of his cars was all over the place in like 3 different states over the course of a year, spotted parked in the driveways or random homes he had no seeming affiliation with. Very weird. I still wonder what I would’ve found if I kept digging.

EDIT: the databases are subscription based, but they’re not unlimited use. You have a certain number of searches per month based on whatever tier you select, and I had the lowest tier since I was just starting out my agency at the time. You also have limits to the features you can use. The more features, the more money. It’s easy to blow through all your credits very fast, especially in cases like this.

Vehicle sighting reports weren’t included and were $25 a search. I believe tow trucks and police vehicles with license plate technology capture the plates as they drive by. One particular vehicle of his just happened to have a lot of hits. I ran my own plate as a test and it’s never been spotted anywhere before, so it’s a hit or miss.

No I didn’t report anything to the police. They honestly wouldn’t give the slightest s**t if I did. Hate to say it, but that’s the truth.

Image credits: Emotional-Count-8595

#6

Worked with a PI every once in a while as a second car for surveillance. Surprised me how many people live off lies. Con artist types and scammers, renter scams were very common.

Employee theft also very common, found that employees from a popular drink company were selling pallets of product on the side. The scam was pretty elaborate to account for the missing product.

Couple cases of husbands who traveled alot for work had multiple families, as in another set of wife and kids.

Found that a young rich woman’s fiancé not only didn’t go to the college he claimed but actually had no degree at all, no job at all, no income at all. Dude would leave the house in a suit and tie and spend most of the day in a diner reading newpapers. Crazy how long he lived off her without her knowledge.

PM_me_punanis:
As someone with one kid and a husband and a full time job, I honestly don’t know how people find the energy to maintain TWO families. My energy sucking vampire of a son ensures I have no energy left for any extramarital shenanigans.

Image credits: TotallyCustom

#7

Way back in like 1998, we surveiled a house for an older guy who thought his younger wife was cheating on him. I wasnt on this shift, but heard the same story from everyone there. They wired the house and waited in the van behind the back fence. Guy leaves on a business trip. Lady gets dropped home by the Chauffeur. He carries her bags into the bedroom.
Suddenly, he slaps her HARD across the face knocking her back onto the bed. One of my coworkers jumped out of the van thinking she’s about to get hurt. Before he gets to the sliding glass door, he hears over the radio (from the other guy watching the video feed), “come on back, she likes it.” She then proceeded to also bang the pool boy.
When my boss informed the client, he just asked, “How much?”
Back then camera equipment was expensive, and we rented it. He just wrote a check for $10k on the spot.
My boss checked in with him later and said the old guy had a private collection of vhs tapes.
So. There’s that.

Image credits: slash-5

#8

I was a fraud investigator for a finance company. I went to interview a small business who we had lent to, got there first thing in the morning. Walked in and had just introduced myself when a dude walked out of the back with a black clean sack. He got a shock I was there dropped the clean sack and bundles of cash just fell out and on to the floor. Said quickly I wasn’t there for that and they needed to pay for the equipment they had secured and not paid a cent for. It was paid before I got back in the office.

Image credits: Salami_sub

#9

I was living in Tokyo. Someone posted an ad looking for someone to do some investigative work. I was broke and interviewed for a job despite not knowing anything about private investigation.

A Japanese woman who spoke good English had a crush on a white guy. She wanted someone to investigate where he hung out, then befriend him, then introduce him to her.

I declined the job. But later on she hired me to do some marketing work for her. Unsurprisingly, one of the worst marketing clients I ever had, purely because she didn’t respect boundaries. Shoulda seen that coming. :p.

Image credits: thesecretmarketer

#10

Heard of this story about a girl from my uni before. She started suspecting her dad having an illicit affair, so her friends decided to channel their inner Nancy Drews and started following the dad around. After a couple of tries, they eventually found him meeting up with the same older woman repeatedly. She was devastated. One day, she decided that she was going to confront the two of them but didn’t want to make it into a public spectacle. She decided to follow them to the woman’s place. She was so confused because she was following them back to her own house. Turns out, the dad bought the mistress a house in the street right behind theirs. Dad also has another daughter 2 years younger than her and named the daughter the exact same name as her.

Image credits: BloomingAtDusk

#11

True story. Hired to watch someone who had been the victim of repeated, serious vandalism. Because of reasons, it was thought to be related to d***s or organized crime, possibly a scheme to sell protection. What we found by watching the victim was tons of d***s, organized crime connections, and revealed the mayor of a small city to be having an affair with someone well connected to the d**g trade. As to the vandalism, an ex-boyfriend was eventually caught in the act; it had nothing to do with the d***s and crime.

Edit:.bc this blew up. It was a very small city, if you’re not from the area you’ve probably never heard of it. My memory is that the mayor was eventually outed for the affair a few years later and that neither the city nor local media really cared; small city, basically a town. I think maybe it also wasn’t much of a secret. All of the affair and d***s were out in the open in public. We would only see things with some deniability, though. Things such as duffle bags being exchanged, we didn’t know what was in the bags but the manner in which they were exchanged, by dead drop, indicated the content were illicit.

Image credits: RocketCartLtd

#12

I’m obviously not a detective or anything, but when my best friend got matched with this girl for an arranged marriage, something about her felt off. Nothing dramatic, just a gut feeling after meeting her once. She was weirdly flirty with me the first time we met, and I couldn’t shake the vibe that she wasn’t taking things seriously.

Me and another friend discussed about it and started casually keeping an eye out. Our offices were in the same area, so we’d see her around now and then. Eventually, we got in touch with someone from her workplace and started hearing she was supposedly having a thing with her boss. And yeah, the boss is married.

We didn’t want to jump to conclusions, but the stories kept adding up. One weekend we got a tip and followed the tip, and yes, caught them at a beach resort 150 kms the city. Saw them hanging out by the pool, holding hands, and staying in the same suite.

All this was happening while both families were planning the engagement, buying outfits, booking venues, the works. It was messy.

We gathered the photos, messages, proof from the hotel guy by giving him some bribes etc and then shared it with my friend. At the next meeting with her family, he calmly showed them everything. The marriage was called off.

Not proud of playing spy, but I’d do it again if it means saving someone close from walking into something like that.

Image credits: ResidentAd8536

#13

Did surveillance on a nurse. She was supposedly so disabled that she couldn’t work. They suspected she was working. Easiest surveillance I ever did. I arrived. She got in her car 10 minutes later. Followed her, with no complication, to a strip club where she went in and began doing her thing.

Club had a posted prohibition on video. So I had to go in and watch her dance so that I could testify that I saw her dancing when it went to court. Over the next few days I followed her to three other strip clubs and did the same.

That month I turned in the sketchiest expense report of my life.

Eventually it went before the WC Board. When the judge asked why she was stripping she just shrugged and said she made twice as much money than when she was nursing.

Benefits got yanked. Insurance company was happy. But the company lawyer gave me the nickname “Detective T*ts” which, most regrettably, stuck and spread to all of the other lawyers I dealt with.

Worse night of my life, man.

Image credits: anon

#14

Not a PI here, but someone who was confronted by one and told it was the weirdest thing he’s had to do.

A roommate I had in college was a strange guy. This guy came from the other side of the country (I’m US). He went out at all hours of the night, never showed up for class, slept during the day, and drank more energy drinks than is healthy. His parents were worried about him, apparently, and hired a PI to trail him.

Now, living in a college dorm in a part of campus where only freshman live makes an adult who isn’t janitorial staff stick out like a sore thumb. So, I picked up fairly quickly that this guy was hanging around the dorms. Thought he was just cruising for some freshman, and didn’t bother him.

A few weeks later, I was walking back from the dining hall, and he approached me (it was a public place) asking if we could talk somewhere private. I was weirded out and told him we could talk right here.

He told me he was a PI hired by my roommates parents to trail him because his parents were concerned, and he wanted to ask me about my roommate’s dorm habits. We then left to the coffee shop to talk about my roommate.

My roommate apparently liked to go walk on the beach at night for stupid amounts of time, hang out at Steak and Shake playing game on his phone and Nintendo DS for hours on end, and cruise thrift shops for some reason. I told the guy that the dude just slept and didn’t even have any personal affects in the room besides his clothes.

The PI and I both realized that this kid pretty much had no direction or motivation in life, and his parents usually pushed him to do everything. He said that this kid’s behavior was the most bizarre pattern of activity he’s pretty much seen.

To explain the kid’s actions, college was the first alone time he’s ever had, and he was savoring it doing whatever he wanted. I ended up feeling for the guy and reached out to him. He changed majors from engineering to a psychology degree because he wanted to learn how the mind worked, and he suddenly became super-interested in college. Ended up being a cool guy once he realized he was not in his parent’s grasp anymore.

Image credits: CyberTractor

#15

Worked as a PI for about a year once when I was much younger. This wasn’t a case I took, which will be obvious by the end why I didn’t.

We had an office on the ground floor of a building near the county courthouse, with a door that opened to the street. This meant we actually got a fair amount of foot traffic. If I had nothing going, I closed the office round 5pm. Around 4:45pm a lady comes in asking all the usual questions. “Are you REALLY a PI?” “What cases do you take?” “How much do you charge?” Yada Yada Yada, I spend 10 minutes going through all that. This lady seem pretty wound up, which is not unusual, people don’t come in looking for a PI when everything is great. Often it’s because they are having one of the worst experiences of their lives and are desperate for help and haven’t gotten it elsewhere.

I ask her to tell me what brought her in today and be as detailed as possible. She tells me that someone stole her ideas and now she’s being followed. I’m thinking, great, potential intellectual property case. I ask her to start from the beginning, what were these ideas? She starts telling me about here last gynecological exam. I immediately stop her and ask her what this has to do with her ideas being stolen. She flips out.

She begins screaming about how the doctor implanted a listening device inside her and that’s how they are stealing her ideas. I do my best not to react. She screams, “You don’t believe me either! But I have proof!” She runs out of the office and comes back a minute later with a large envelope. She pulls out x-rays of her pelvic region and shoves them in my face. “See! Right there, that white spot on my ovary, that’s the listening device!” I agree that there is a small white dot, but tell her I’m not a doctor or an expert in listening devices and can’t confirm that it is one. In reality, it didn’t look like anything to me, I know it wasn’t an electronic device of any kind, let allow one that can capture you ideas and transmit them to vans that were following you around now.

She goes on to tell me how the doctor was in on it and they were stealing her ideas and making them into TV shows for Telemundo. This is the part where I tell you this middle aged, blonde haired, blue eyed lady didn’t speak a word of spanish.

I ask her about the vans that were following her. They were different colors and often different drivers. But they were definitely following her around and that’s how they were collecting her ideas. I’m looking for a polite way to tell this lady I won’t be taking her case, but she won’t let up and insists I do something about it. I finally catch a break. I tell her the retainer amount I would need to get started. She responds, “Well I don’t have that kind of money. When we win in court you can have half the settlement.”

In the state I live in, only lawyers can work on contingency. Meaning their payment is contingent on them winning the case. PIs and all people that might work for these lawyers still have to be paid no matter what. I tell the lady this. I thought she was about to explode. I tell her I can’t break the law, but if she were to find a lawyer willing to take up her case, I could work for that lawyer as their PI.

She calms down and says thanks for hearing her out. I say no problem. I ask her if there was a family member she could call or a doctor she did trust that she could see. She tells me she’s not crazy and storms out. I felt horrible for her, she was obviously living in terror and needed professional help. This was the first time I encountered the seriously mentally ill. In retrospect, I should have called the police and tried to have them intervene, I regret that. I can look back now and cut myself some slack for being young, and caught alone and off guard, but I still wish I would have done more. At the time I just wanted to get her to leave peacefully.

Image credits: anon

#16

I’ve worked a few bizarre cases, including one involving a stolen horse and almost getting shot by rednecks. But due to legal reasons, not sure if I can mention that one.

There was a workers compensation case I worked last year. I was told to get film of this older lady who had supposedly be on total disability due to a severe ankle injury. Seems cut in dry. But she lived in a motel in the middle of nowhere Pennsylvania. The motel was called “Johnnies” I looked up the place online, and found reviews of it on google. There were really sh**ty reviews including one that said the place was mostly run by the owner’s son, who was a druggie and would ask people who stayed there if he could buy any prescription drugs they had. That isn’t sketchy at all.

So I show up to this ‘motel’ which looked like it hasn’t been renovated in 40 years. It was a small motel, had about 14 rooms. I have no idea what room the person I’m supposed to find is in. I figure I should talk to someone at the front desk. There is no front desk. The office part of the motel looked boarded up. But next to it was one of the motel rooms, and in the window of the room was an “Open” sign. On the door it was a sign that said “office” and instructions for long term customers of the hotel on where to drop their payment. There was a door bell. I rang it and waited. The guy who opened the door looked exactly like Kenny Powers from Eastbound and Down. He was wearing a Ninja Turtles t-shirt and Hawaiian shorts. He tells me to come in. I walk in and what I walk into is just a room with 1 desk. Nothing else. There was shag carpeting and really dark colored walls and a lava lamp on the desk. I realize that this was the owner’s son, Johnny Jr. I give him some fake story how I’m an insurance adjust looking for this lady, he then replies “Oh Mary? She lives in the room next to me, want me to go get her?” This is a problem because I have absolutely no backstory on what to tell this lady. She was repped by an attorney and likely knew a PI might be looking for her. I tell him, no, I just needed to confirm she lived her and bolted.

Now, park in the parking lot with view of the room Johnny Jr pointed at. A couple hours go by and then some old guy is standing near my car getting stuff out of his car. Johnny Jr walks out and starts talking to him. I realize the older guy is Johnny Sr. They are literally standing right next to my car and I can hear everything they say. What proceeds to happen is they start talking about me, well at least the “insurance adjuster” who visited earlier. Johnny Sr having seen some sh*t in his day immediately says “that wasn’t an insurance adjust you idiot, that was a PI, insurance adjusters don’t work on Sunday” He tells Johnny Jr to tell Mary to watch out that a PI might be in the parking lot.

My car is tinted. I think I’ll be fine. Except, the parking lot I’m in is shared with a Diner. The owner of the diner comes out and starts talking to Johnny Sr. Apparently I parked in front of a shed that the cleaning staff for the motel use. Johnny Sr now starts talking to the owner of the diner asking her if my car belonged to any of her employees or any of the people in the diner currently. She says she’ll ask and she leaves. Johnny Sr then goes into on of the motel rooms, where apparently he lives. He constantly stands in the door way looking at my car. I leave as soon as he looks the other way.

I would come back later in the day and would get film of the lady I was supposed to watch. Was totally faking her injury. Johnny Jr and his girlfriend actually came out a couple times and tried figuring out what cars might be a PI’s car. But because they saw my car earlier that day, they didn’t seem to suspect it as suspicious.

Image credits: anon

#17

I’m a PI (among other things.)

I haven’t had any bizarre tasks, though I have had some interesting situations, and I’ve performed surveillance on cheating spouses as well as factual worker’s compensation and public liability matters.

One matter which really made an impression on me was where a person had a fatal vehicle incident and a claim was made that it was a workplace injury. I don’t know what on earth happened with this claim but it was five years before the insurer gave it to me.

There were some questions about it – the person making the claim alleged to be the worker’s wife, though work colleagues did not know her, and also the incident was almost 200km from the workplace.

When I spoke to former colleagues a lot of them struggled to remember him. This really was so sad. It left a deep impression on me that what are we once we are dead if we are not even memories.

I did, however, learn he stayed at a caravan park during the working week. I called that place but the owner said it had changed hands and he didn’t know the guy, he didn’t have any old records, and he didn’t know where the former owner was. He did remember the former owner’s name however.

I called everyone in the phone book for the state with that name. I finally got my man, and he remembered the deceased vividly … along with his wife and son. It was tremendous! I learned the guy would stay near the workplace during the week and travel back home, to a remote town, for weekends.

I drove all the way to that town but couldn’t find the wife. She wasn’t at any address I had, nor did she answer her phone. I got petrol and asked at the counter if they knew the family, and they said it might be so-and-so and directed me to a house. I went there, turned out to be the wife’s parents, they called the daughter, she arrived and both mother and daughter had a big cry while showing me all their photographs of the guy. It was very moving, and I was so relieved to have real evidence the guy ever actually existed after how his co-workers were finding it hard to remember him.

The story was very sad; he died on the way to work on a Monday morning. Normally he would travel to the caravan on a Friday night but this particular weekend was mother’s day. He stayed Sunday night and travelled Monday, early in the morning, ran off the road and passed away 🙁

I was able to determine the lady was genuinely his wife, that he was on his way to the workplace, that it was his regular route to work, and so on. I supplied this to the insurer. I never – well, rarely ever – hear what happens to a matter so I only hope it was finally settled.

Image credits: mgdmw

#18

FINALLY! A question I can answer! Been a P.I. For a going on a year now and the strangest case I had was of a woman asking us to find out if her husband was cheating on her. She said there was something off in the house as if feeling something and she wanted to know what it was. So she suspected her husband of cheating.

So I show up and install Nanny Cam’s in her house for the weekend upon her approval and where to place them. She works all weekend and this was the best route. Well 3 days go by and I collect the footage and come to find out the husband was “touching” his 8 year old step daughter. After seeing that I rushed to the court house with a copy of the footage and got a court order for the police to go and get him.

Image credits: AvoidableBoat67

#19

All right, here goes. After I got out of the Navy, I worked for one of the top PI firms in Houston. Because of my electronics background, I’d usually go along on the jobs where were were checking for bugs and hidden surveillance devices.

We got a call from a client who was sure that his office was bugged because his client knew everything that he was doing before he did it. His office was a mobile trailer that was on his client’s site. He was a subcontractor for a big oilfield construction company.

We did a full electronic sweep and found nothing (this was back in the early nineties, didn’t have to worry about burst transmissions, etc.) No devices implanted in his phones. He insisted on a full physical sweep of the trailer, inside and out. So we crawled under the trailer and got a ladder and inspected the roof. Still nothing.

We’re getting ready to leave and he says: “Look, I’m not crazy. Pick up the phone, press 9 to get an outside line, and you’ll start hearing all sorts or clicky sounds.” Turns our his office phones were routed through the corporate PBX of his client. They didn’t have to bug his office, they could just “pick up an extension” inside the main building and listen in to whatever they wanted. We weren’t even sure if it was illegal. We advised him to install a private phone line that he paid for if he wanted private conversations. We ended up billing him like two grand for that visit.

Image credits: dcfix

#20

My work partner and I were watching a guy who was cheating on his wife. We were at a restaurant where they were eating dinner together. Had snuck over to his car to put a GPS tracker underneath the fender. At the same time there was another PI team working to put a PI tracker on the girlfriend’s car lol. We never made contact with the other team, but we sort of gave each other just a wink and a nod. Turns out they worked at the same hospital and we’re each cheating on their spouses with each other but we’re also cheating on each other with multiple other people. It was a hot mess and a lot to keep track of.

Image credits: Pocketeer1

#21

Former PI, about 30 years ago.

For me, the amount of people faking disability claims was huge. It made up at least 70% of our cases but it was also easy to prove..way more than other types of cases.

Normally, we’d just hang outside their house and wait for them to take groceries out of their trunk, walk down their porch steps, etc.

But one hilarious case that I will never forget was the one where a man claimed he hurt his shoulder and lost movement of his right arm as a result. We waited outside his house, and on day 1 he came out and got into his car. So we followed him….to the batting cages where we recorded him swinging a bat all day.

Image credits: ImprovementFar5054

#22

Worked as a PI for 9 months, the company I was with investigated employee workers comp fraud. I’d follow people who supposedly had injuries so debilitating they couldn’t work, and then film them doing things like carrying 3 jugs of detergent through a grocery store, or lifting a massive concrete tortoise out of a garden bed and moving it to the other side of the yard.

Most interesting thing was a job I did in another state, and I filmed a guy about a mile away in farm field slowly take apart a small plane he had sitting in a field over a period of 8 hours when he supposedly had a back injury so bad he couldn’t lift 10 pounds. Maxed out my camera memory, ended up taking pictures the last 4 hours every time he moved a piece of plane.

Small piece of advice: if you’re committing workers comp fraud and the company’s insurance tells you to go to a specific doctor…they have paid PI people to wait for you there and follow you home/around for the day. They wanted to get you in a specific place to be followed after you pretended to be hurt so they can show after you went and did things you shouldn’t be able to.

Image credits: Tee_Hee_Wat

#23

Caught a guy on disability carpooling Amish kids to school.

Was insurance fraud case. in southern MD. For a week I watched a supposed completely disabled person shuttle kids in a blue station wagon to a public school. Pick up and drop off. Long time ago, 20+ years, video’d it all on a handheld VHS cam. Even got video of what looked like a cash payout by one of the parents at the end of the week.
He then drove to the local 7-11 and bought a ‘bagfull’ of scratch offs. Weird times.

Image credits: Ravenswind

#24

We did mostly disability fraud. Most PI work is insurance because it’s consistent and easy to bill.

It’s basically professional doorknob watching. Show up to site around 4am, sit there all day and see nothing. Take timestampped photo or video every hour. Sit in car all day peeing in Gatorade bottles and watching movies. Go home, submit report that nothing happened and you saw nothing.

Sometimes catch people claiming disability working out at a gym or cleaning gutters, basic normal stuff that people claiming disability shouldn’t be able to do.

Weirdest thing I ever saw was a municipal client that wanted surveillance on a dude suspected of violating a zoning ordinance by manufacturing fertilizer in his house. Never confirmed any of that but that would be stinky if true.

Sometimes you have to follow the subject in a vehicle and that requires a crazy amount of traffic violations, mostly running red lights and speeding.

Most contracts want you to break surveillance if you get noticed. You just switch cars and try again the next day.

All things considered, awful job. Little career growth. Crazy hours. Inconsistent work. Licenses can be difficult to acquire so mostly you work for a company that holds a license and never progress. You’ll miss holidays and family events. S**t retirement.

If you think you like that work, be a cop and then make detective. At least you get a pension.

Image credits: Temporary_Anybody279

#25

I was slightly involved in an investigation by a private investigator. Involved in that he contacted me twice. First, by “accidentally” getting gas at the pump next to me in a not too new, appropriately dirty truck and starting a conversation about hay that led to him eventually asking indirectly about the subject of the investigation who was a not too close neighbor. My impression at the time was that he was a slightly awkward, but friendly, person just trying to get some feed for his animals.

A few weeks later, he stopped by my farm. Different personality. Polite, efficient and direct, driving a typical fleet sedan. Mentioned the previous encounter and explained he was conducting an investigation which was complete. He was just following up to see if I had any comments about the guy in the event it went to court.

Turns out he was on disability due to painful neck and back injuries that caused weakness in his arms rendering him unable to work as a plumber. Selling hay in 80lb bales which he was was recorded throwing onto a wagon several hundred times over the course of the investigation.

The investigator was impressive. My first contact with him left me thinking he was totally harmless. My second showed him to be a competent person.

It was an interesting experience.

Image credits: Uncanevale

#26

Working for an insurance company in the IT department and created a secured file server for our disability insurance investigator to upload video. Worked closely with him so I got all the stories. Primarily just catching people who were 100% disabled building fences, unloading bags of groceries and walking them up two flights of stairs, just doing things things they physically said they cannot do.

Image credits: NeutralTarget

#27

A PI followed a woman who seemed to be living way beyond her means. no fraud, she was a ghostwriter behind several huge influencer brands, running their entire marketing strategy in the background

Quietly making six figures while staying completely anonymous.

Image credits: Extra-Tradition-8360

#28

My story is about hiring a PI. In the 1970s, pre computers, cell phones, and cameras. Managed a car rental place in Canada and had a long term rental not come back. Local people, so I contacted a name I had in an old file. Guy comes in, jeans and a T-shirt, young not even 30. I explained we had little to no information, credit card, home address and names. He found them living in a hotel in San Francisco and he did it with in 2 days. Still think about how the hell he did that.

Image credits: kevanbruce

#29

My girl worked for the usps. She was part of the p*dophile investigators.

One day I see her at the library in the middle of the day. I stop in and was going to say hi when she waved me off. She was super flirty with some guy at a computer terminal.

Yep, he was a p*dophile and that’s when I found out what she did. She was getting the sites he visited, and was trying to get other info off the computer being used.

So the lesson was, don’t let your kids go to the library.

Image credits: KroxhKanible

#30

A good friend was self employed and had full insurance cover ‘just in case’. He did get injured while working and couldn’t walk unaided for months. It turned out that his business owners compensation insurance was subject to a very high percentage of fraudulent claims so P.I. investigation was normal.

Picture a street of a better class of middle income houses. Good weather and my friend working in his yard doing landscaping by sitting down and dragging his injured leg along. He did this for hours every day. Each day, at lunchtime, he would get up on his crutches, hobble over to the car where two investigators were watching and filming him, and offer them to come into his house to have coffee or a cold drink. Every day for three weeks, 21 days. They angrily refused each time.

After the third week the observations dropped to one or two spot checks each week for the months he needed to get back walking.

We guesstimate the cost of the investigation was way more than the insurance payout.

Image credits: CurveAccomplished642

#31

I located and assisted in serving my husbands sleezy former boss which led to his arrest on federal charges. Good times.

#32

I’ll have to think about how to share the information without violating client confidentiality, court orders and numerous NDAs.
But there have been a few WTF moments, over the course of 30 years.

#33

A couple was divorcing and the wife was sure her husband was sticking random items of hers up his a**.

He was.

#34

I have a story about this. My Brother was a PI in the early 90’s. He worked for a law firm. I was in my early 20’s and so he got me a gig as a process server.

He was working a particularly nasty divorce case. Husband was a Jordanian national married to an american woman (one of several wives) who was over being the broodmare in the family and wanted out. Also, she worked for Nasa.

He was tasked with going into their house, which was in her name (she wasn’t living there, she was in an apartment until this was settled) and getting a briefcase with financial information in it. Since I was the process server, I had to go along in case someone was home for whatever reason.

We went and waited down the road until everyone left and went in and got the briefcase. no big deal. We take it back to the attorney’s office and he calls the lady and says he has it. She gives him the combination he opens it and it was full of technical plans from Boeing for the Apache helicopter.

Attorney says “Fuck”, instantly shuts the briefcase, tells me and my brother to leave now, so we did. We never heard any more about that case at all, other than he contacted the FBI over it.

#35

Not PI related but outed by an Apple watch. A tale from SFO to a small town in Tamil Nadu, India

My friend runs his own business in a very small town in India. his clientele is the slightly upper middle class for that area, people who have land and do agri biz.

He called me up and told me to get him a apple watch and other gizmos when I told him I was going to the USA on a biz trip. I duly get the stuff, call him up, tell him the costs which he pays. I now needed to send the stuff to him and it’s going to take time and I don’t want to courier expensive items. Ask around and there’s one guy who was going to the same town and that too in 2 days. great. pack it and tell my friend and he also gets the goods over the weekend.

He calls me over the weekend for the usual chitchat and goes

“bro, what kind of office colleagues do you have/know?”

what?

that fellow who came and gave the apple kit, you know him?

no, just that he’s in a different team and he’s from your place, why?

right, here’s the h***y side you’ll not believe, listen, the fellow came and gave the kit; there was this other chap who saw him and asked me, how do I know him. I said, i don’t know him but he work’s in my friend’s firm and my friend sent this kit through him

uh-huh, best you don’t interact with him

why?

see, this fellow has married twice and it’s like a TV soap drama. this fellow went to the USA and worked there for 6 years; been seeing another Indian girl there, married her there and also has a kid there. meanwhile, his parents found a girl match for him in this town(family friend’s daughter) and he too agreed to marriage without telling them anything.

saar, he married the girl, sets her up in his parents house; he went to USA again, got the other girl and kid and set them up in the next street saar! Idiot! and it took them 3 weeks to figure out all of this. his parents fully supported the girl he married here and had to threaten their own son to drop the other girl. this idiot fellow didn’t do anything at all to resolve the situation. so now this whole town knows, he’s got 2 wives and his parents are furious at him for bringing shame to them.

don’t interact with him.

MY friend recites all this and I got progressively slack jawed. I make a few workplace checks and realise no one knows this in office and he works everyday in office and goes to his hometown once in 2 months.

effectively ostracized. there’s more whiteboard diagramming stuff of who knew when, what and how other parties got involved etc but it’s all Tamil culture stuff which would make it a book length story and not fit a post

All because of an apple kit.

#36

Woman that melted into a carpet.
Florida heat. Wellness search gone wrong. Always have some emergency alert system here if you don’t have heat but ugh.

#37

Doing a standard pre-employment background check on a guy, found that he was found guilty in a sexual harassment case. Didn’t have the case details at that point and the guy denied it was him. Pulled more details from the case and confirmed that it was definitely him… And that he was convicted of indecent exposure. The guy finally admitted it was him, but claimed it wasn’t as bad as it seemed. Pulled the court transcripts. Turns out he flashed a 12-year-old on the beach and said “ever seen one of these before?” He did not get the job.

#38

I worked for a PI company that mostly handled workers compensation cases for insurance companies or other employers.

Assigned to a case in Seattle where a guy was claiming am upper back and shoulder injury. After a few hours on site at his house, he pulls up in a truck, proceeds to empty the truck bed of landscaping equipment ALONE. After he has put everything away, he walks over to the side of his neighbors house, pulls out a piece of the siding of the building, withdraws a crack pipe and smokes it in front of me, all on camera.

Another case in Texas, I was following a guy (Back injury) to the mall where he met up with a woman that was NOT his wife (I had already identified her the previous day) and followed them as they shopped around and then back to his vehicle where they proceeded to have sex in the car IN THE MIDDLE OF THE MALL PARKING LOT! I filmed it of course, but I had to call my boss to make sure that I could send this to the client. She was kinda hot too so…

#39

I was asked to help my boss fire another investigator do to his short temper. I was told to arrive at 7:30 because he likes to arrive at 8:00.

So like any other day I woke up and started to drive to work through a fucking blizzard and didn’t end up getting there till 7:40. Go to my boss and says he already fired the guy.

What the fuck man what if he lashed out and what not and I wasn’t there.

His reply was he didn’t, but he wanted me to stick around just in case.

So I sat there for 4 hours drinking coffee on double time which was great until I had to file the 2 page report on me drinking coffee

Tldr. Drank coffee for 35 bucks an hour.

#40

I did surveillance for insurance fraud/workers comp cases for a short time. We would usually just be assigned to someone for a couple of days, unless we found something that warranted more time. On my first day watching this guy he leaves his house about 7 hours into the 8 hour (for me) day. I follow him out of the neighborhood, out of the town… onto the highway… still on the highway… into the metro area… into downtown (oh sh*t where is this guy going to?) … and into a valet parking ramp. I panicked a bit because I had my video camera, laptop, and all the background paperwork sitting on the passenger seat next to me. I was able to shove all that stuff away or grab it into a pocket before I turned the car over to the valet. Ended up riding the elevator out of the garage with the guy and his family. They were going to see the seasonal holiday light parade thing, so that was nice to watch at least.

#41

A college of mine was a PI.

He said the majority of his casework isn’t tailing people but serving court notices. He told me of a variety of really slimy ways he’d serve people, including disguises, high pressure tactics and weird social engineering.

He’s out of it now because he’d had too many close calls. Serving divorce papers or notices of being sued where you have no idea of the state of mind of the person you’re serving to could get interesting to say the least.

#42

I got hired to follow another investigator who, turns out, was hired to follow me.

#43

One time I was hired by this really famous author to test the security system in his Hawaii vacation home. His British caretaker set his two dogs on me and I had to escape by hot wiring his Ferrari.

#44

Not a PI, but I met one. I was at my friend’s house and he got a knock on the door. The dude was black (EDIT: Congolese to be specific).

“Hello, sir, are you X?”

“Yeah, why?”

“[explains that he’s a PI and that he’d like to talk in private]”

“Nah, I’m fine just talking here at the door.”

“[shows him a picture] Do you know this man? His name is Y.”

“Yeah, that’s my great-uncle, he’s vacationing in the Congo right now, why?”

“I’m sorry sir, but your great-uncle died of hepatitis. [elaborates how his great-uncle, a priest, banged some hooker and got infected and died]”

I was in the living room eating pizza the whole time, pretending to be watching TV.

#45

A private investigator came into the bar I was bartending at years ago and showed me two pictures. One of a girl in her early 20’s that her family was trying to find; the other of a guy in his late 20’s that they suspected she had run away with.

The guy in the picture had a charge on his debit card from my bar a week earlier so the investigator came in hoping that I would remember if the girl was with him that night.

I did not recognize the girl at all but I remembered the guy. He had come in with two other guys around his age, they got pretty drunk but all they really did was shoot pool. They didn’t cause any problems and they actually tipped me really well. I never heard anything else about the girl so I don’t know if the family eventually found her or if she disappeared for good. I just now remembered that her first name was Katie. I can’t remember the guys name though.

#46

It was one of my last cases that I worked on. It was for a child custody/paternity case.This case was the one that made me rethink what I was doing and I got very disturbed by what I was asked to do. This is the case that made me stop being a PI

Our client was denying that the child in question was actually his and was fighting the child support case. He believed that the mother of the child was a serial adulterer. So much so that he spent THOUSANDS on the case for us to make sure there was evidence to support his claim.

The icing on the “sh*t cake” was when my case manager told me that client wanted video evidence that the child did not look like him. The client told us that we had to record the child at play.

So here I am, beside a playground, in a completely limo tinted car, videotaping a 9 year old. I couldn’t have felt worse about my life choices. To this day I have never felt like such a creep before. I hated that case and the case manager.

Two weeks later I handed in my resignation.

#47

Client wanted to know why her dog was getting fat.

Turns out the dog was getting fed by almost every stranger it encountered while wandering around outside during the day.

karmagirl314:
It’s called a hustle sweetheart.

#48

I was asked by a lady to investigate her husband because he might be cheating on her. He used to come back late at night with smell of womans perfume. Turns out he was taking dancing classes and he didn’t tell his wife.

#49

I found a lady who’d been missing for twenty years out of pure, dumb luck. I was getting lunch another town over and she walked out of a resale shop across the street. It was so unexpected that the only footage I could get on her was with my sh**ty phone camera.

Otherwise, I don’t get a ton of “bizarre” cases. Most of the time, I’m just doing insurance fraud cases since that’s where the money is. The most interesting part is looking at their background info and piecing together what kind of person they are based on their spending habits. Then you take that information, make a quick and dirty psychological profile, and try to predict their movements based on it. I’ve gotten pretty good at it.

#50

I was asked to train who was going to replace me by my new supervisor, who was in the process of firing all the old blood to pack the office with her friends. It was incredibly obvious that I was next on the list, and she wanted me to train a 19 year old idiot (seriously, she honestly found out Santa wasn’t real THE YEAR BEFORE) to do a very important job, including many tasks where I was the only person in the office who could do it.

But I tried. I could not force her to pay attention to me, so I just explained everything while she played on her phone sitting next to me in my cube. Did not work out well for them, boss actually chewed me out for not training her when everyone in the small office knew I went over the quirks of the McDonald’s contract with her for nearly half a day – the salespeople had promised them the world to land the contract, and they had an extremely complicated system for adding new franchisees that was all on a spreadsheet that only I knew how to maintain. Not long after I was let go, we were no longer the official background check company for McDonalds, which amounted to about half of our corporate clients.

That’s about it. Being a PI was just a mildly interesting aspect of what was otherwise a typical office job with typical office drama.

#51

I once got hired to watch these two other PIs follow each other around and give them both a score out of ten each day. It was SUPER weird, and the score cards kept going missing from my car.

#52

OK, not a PI, but my boss hired one.

He never told me but I was snooping around the network one day and came across a document that was cut-and-paste e-mails between the boss and a PI.

I worked for a playground design/construction company. Very small, and the boss was an absolute prick. He may have been bipolar because he would be happy one minute and then the tiniest problem (like a slide being a different colour to what he thought it should be) would send him off the rails for the rest of the day.

Anyway, according to this document, he was suspicious that his competitor was able to offer playgrounds cheaper than him and still make money. He had a strong suspicion that the competitor was using illegal immigrants to build the playgrounds and paying them in cash, for less than the minimum wage. This is in Australia, not the US, so this is probably very uncommon here.

The PI went to a construction site and talked to the workers. He returned a report that stated that the workers were co-operative, they did not appear to be foreign, they spoke English very well, they even showed him their drivers licences. He left totally satisfied that the workers were legitimate Australian citizens.

Boss refused to pay.

The rest of the document was the PI arguing that he did work and should be paid for it (a few thousand dollars I think) while a**hole boss’ argument was that the workers were definitely illegal immigrants, he just knew it, and if the PI couldn’t prove it then he wasn’t a very good PI and therefore shouldn’t be paid.

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