30 Private Investigators Share The Most Unexpected Twists They’ve Ever Seen

Reddit is a treasure trove of real-life stories, but every now and then, a thread surfaces that truly grabs your attention. Someone asked a serious question on the site: “Private Investigators of Reddit, what is the most interesting thing you’ve encountered on the job?”

#1

Image source: Extra-Tradition-8360, Getty Images / unsplash (not the actual photo)

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.

#2

Image source: trackerjakker, Josh Hild / unsplash (not the actual photo)

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!”

#3

Image source: Which_Algae1157, Carol Highsmith’s America / unsplash (not the actual photo)

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.

#4

Image source: CyberTractor, Adam Borkowski / unsplash (not the actual photo)

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.

#5

Image source: AvoidableBoat67, EJ Li / unsplash (not the actual photo)

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.

#6

Image source: questionguy1000, Hc Digital / unsplash (not the actual photo)

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.

#7

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.

Image source: anon

#8

Image source: ResidentAd8536, Getty Images / unsplash (not the actual photo)

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.

#9

Image source: BloomingAtDusk, HiveBoxx / unsplash (not the actual photo)

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.

#10

Image source: anon, Aleksandr Popov / unsplash (not the actual photo)

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.

#11

Image source: kevanbruce, Benjamin Fay / unsplash (not the actual photo)

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.

#12

Image source: sock________puppet, Andrej Lišakov / unsplash (not the actual photo)

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.

#13

Image source: mgdmw, Nini FromParis / unsplash (not the actual photo)

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.

#14

Image source: Uncanevale, Rebecca Ritchie / unsplash (not the actual photo)

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.

#15

Image source: KroxhKanible, Judy Beth Morris / unsplash (not the actual photo)

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.

#16

Image source: CurveAccomplished642, Claudio Schwarz / unsplash (not the actual photo)

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.

#17

Image source: dcfix, A F / unsplash (not the actual photo)

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.

#18

Image source: TotallyCustom, frank mckenna / unsplash (not the actual photo)

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.

#19

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.

Image source: anon

#20

Image source: Pocketeer1

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.

#21

Image source: anon, Getty Images / unsplash (not the actual photo)

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.

#22

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.

Image source: themeowfactory

#23

Image source: thesecretmarketer, Gildásio Filho / unsplash (not the actual photo)

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.

#24

Image source: ImprovementFar5054, Mathias Reding / unsplash (not the actual photo)

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.

#25

Image source: slash-5, Gabriel Petry / unsplash (not the actual photo)

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.

#26

Image source: Tee_Hee_Wat, Getty Images / unsplash (not the actual photo)

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.

#27

Image source: Emotional-Count-8595, Randy Kinne / unsplash (not the actual photo)

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.

#28

Image source: Salami_sub, Sven Brandsma / unsplash (not the actual photo)

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.

#29

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

He was.

Image source: you_are_d00med

#30

Image source: RocketCartLtd, Koshu Kunii / unsplash (not the actual photo)

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.