Those of us who haven’t worked as private investigators might assume that they spend all day neck-deep in cool cases, drinking coffee, and meeting interesting clients, like in black-and-white film noir crime dramas. However, reality is… let’s just say that it ranges from mildly to wildly different.

A group of PIs took to a fascinating online thread to vent about the most bizarre and confusing jobs they’ve ever been assigned. Some of them were so off-putting that a handful of them even decided to quit! Check out their stories below to uncover just how varied the life of a private investigator really is.

#1

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

He was.

Stiflerradi:

Why does every thing smell like sh*t?!
Ohhh…

Image credits: you_are_d00med

#2

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*ll.

fwng:

This would be me as a PI. I wouldn’t even need someone to give me a case. I’d just do it.

Image credits: questionguy1000

#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.

randomuser8765:

Wow, she must have really good hearing and smell.

Neilsen17:

Smells like a left turn in 400ft.

Image credits: trackerjakker

Being a private investigator is no easy task. Unfortunately, it’s not all glitz, glam, adventure, and cool cases like you see on the silver screen and on TV. Far from every task is going to be as exciting as you’d like it to be. And unless you’ve already got a stellar reputation, you’ll have to put in a ton of effort to polish your brand and attract a steady stream of clients.

The Centre for Security Training & Management notes that the following skills and qualities are important for private investigators to have if they want to be effective at their jobs:

1. Good observation skills and a keen eye for detail
2. Sound legal knowledge
3. An aptitude for photography and taking videos
4. Computer literacy and tech-savviness
5. Good people and communication skills
6. Confidentiality and discretion
7. Organization
8. Responsiveness and efficiency
9. Analytical skills
10. Resourcefulness
11. Tenacity and determination

#4

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**s” which, most regrettably, stuck and spread to all of the other lawyers I dealt with.

Worse night of my life, man.

Image credits: anon

#5

I had a case referred to me by an attorney I worked for involving a woman who was convinced that her condo maintenance man was going into her home while she was gone and moving things around. She had bought the condo from him originally. (In other words, it was his former condo).

I met her to discuss the case and she seemed rational, she was an attractive older woman, the guy would obviously be familiar with the condo layout and would have access, and hell, I’ve seen weirder things. So we proceeded. She agreed to let me install a hidden camera setup with a motion detector. She was to call me if anything happened to make her think he’d been there.
A couple of days go by and she calls. I go by and get the tape (this was before digital recording) and check it out. There’s nothing on it but her. I meet her to tell her this and she says, ” He must have some machine that makes him invisible. He’s a space alien, after all.” She had not previously mentioned this vital tidbit of information.

I told her that that level of technology was beyond my ability to deal with and that we should talk it over with her attorney to determine the best course of action going forward.
I called the attorney to let him know that our client had some issues, and we were able to get her some psychological help.

But most importantly, her check was good. :).

Image credits: DoktorInferno

#6

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 credits: anon

According to the Centre for Security Training & Management, private investigators usually aren’t bound by the same confidentiality agreements as, say, legal professionals or medical experts. However, your clients will appreciate you being discreet.

“Always maintain high levels of confidentiality in all your interactions. Think of it as a great way to get your clients’ trust. You can also go the extra mile of having a confidentiality policy.” This also means that you should really watch what you say about any cases you’re doing, during your leisure time, when you’re off the clock.

Being resilient is a huge plus, too. Your cases won’t always go the way you expect them to. “A dedicated investigator doesn’t give up. Your determination is often the deciding factor in ferreting out the truth.”

#7

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 s****y 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.

avesthasnosleeves:

So many questions… How did you know it was her? I mean…20 years – she’d look totally different, right? And why was she missing? We want answers! (Ok, maybe just me, but…)

44Renegade (OP):

She actually looked about the same, plus some wrinkles and a little rattier hair. I’d also literally just gotten finished looking over the case file, so the image was still fresh in my mind. I also have the special gift of never forgetting faces. If I meet you once, I’ll recognize you five years from now, even if I don’t recall from where.
She basically just went off the grid for personal reasons. Finding her was kind of a pain in the ass, and truth be told, if it wasn’t for that happy accident, I probably wouldn’t have found her. All I had to go on was a vague last known location. I was hired by her sister who had received instructions to find her from their father shortly before he passed away. The video was a little spotty, but it was enough to confirm that she was the person I was looking for. I never got to witness the reunion and I’m not sure what happened to them after my job was done.

Image credits: 44Renegade

#8

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.

That was the most bizarre thing that ever happened to me during my time as a PI, but there were a couple of close runners-up.

Image credits: anon

#9

I was asked to help my boss fire another investigator due 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 f*****g blizzard and didn’t end up getting there till 7:40. Go to my boss and says he already fired the guy.

What the f**k 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.

Image credits: Blinkanbgon

Meanwhile, registered private investigators Anderson & Co stress the fact that PIs ought to be dedicated, diligent, and discreet. They should be meticulous in how they document details and gather evidence. What’s more, they ought to have good critical thinking and problem-solving skills, know how to use modern technology and surveillance equipment, and have strong research skills.

Furthermore, integrity, confidentiality, persistence, and patience are also key for a PI! That’s on top of taking good care of your health so you have the energy to do your job well. “Stamina is also important during long stakeouts or surveillance tasks. For example, static surveillance, whereby a surveillance operative may be instructed to observe a property for twelve hours, is common. It is important that throughout that time they don’t fall asleep, or start scrolling their social media, and taking calls,” Anderson & Co notes.

#10

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 “s**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.

Image credits: Kryimsson

#11

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

#12

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: mprovementFar5054

Which of these private investigator stories captured your imagination the most, Pandas? Have you ever worked as a PI before or know someone who’s a detective? Do you think you’d make a good PI, or do you prefer the more romanticized version of their jobs, like in film noir flicks?

Grab a cup of coffee, put on a fancy vintage hat, and share your thoughts in the comments at the bottom of this post!

#13

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

#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

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 drugs 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

#16

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 were 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

#17

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

#18

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.

Image credits: thesecretmarketer

#19

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

#20

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

#21

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 “F**k”, 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.

#22

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.

#23

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 h****r and got infected and died]”

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

#24

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.

#25

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 s**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.

#26

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 p***k. 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*****e 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.

#27

Was asked by a prospective client to kidnap a child who’s parents were in the middle of an ugly custody battle, the one parent was keeping the child in violation of a court order and this family member thought this would be the easiest solution, nope, passed on that one. One of the funniest things about the PI business that we saw over and over was clients coming in mad as hell wanting something done saying “cost is no object”, right up until we told them we charged $100 per hour, then cost suddenly became an object.

#28

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.

#29

Caught a guy on disability carpooling Amish kids to school.

#30

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.

#31

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.

#32

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 s*x 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…

#33

My uncle is a PI. He got tasked with investigating a collision at an intersection. He found a nearby business that happened to have a camera facing the road which would have collected the footage and got said footage of the collision.

The client was definitely in the wrong and caused the accident, then the client was seen a***ing the other driver while damaging his own car further.

It was meant to be an insurance scam where the client could say they hired a PI but found nothing which legitimizes his word, however he rolled snake eyes and ended up incriminating himself.

My uncle still got paid.

#34

Way late to the party. Also not the PI, I’m the person who paid the PI bill for this one.

We hired a PI to provide proof of life.

The guy suing me completely disappeared, to the point where for 6 months even his own lawyer could not reach him. His lawyer is 400 miles away. No one had the guy’s real address (only address anyone had was a FedEx store that he did not work at). But the employees did say that the guy comes in every few days to collect mail.

Since we had so little information we actually had a PI sit out front the FedEx store until we got a picture of the guy alive.

That whole case (still ongoing) is a huge pile of WTF. My lawyer friends enjoy laughing at me over the lawsuit because it is so bizarre.

#35

There once was this dude who had his emails leaked. I had to sift through many of them and there was countless of weird instances where words for various food was used in conexts that didn’t make sense. I realized it had to be code for something and after further research I realized the words where most likely code for young children and I was dealing with p********s. I ended up getting help from the public and the case started trending on twitter. Turns out we were uncovering a major network of businesses that are used or have been used as human trafficking fronts.

He hasn’t been arrested yet though.

#36

Not my personal experience but one of my Grandfather’s countless “war stories”:

After retiring as a cop, he took on a PI gig and was once involved in an open/shut injury related case which was about to award a massive insurance payout and go forward with a huge lawsuit.

The person he was investigating was apparently made to be quadriplegic after a work related accident, he even had a doctor confirm that he indeed had irreversibly damaged his limbs. My Grandfather decides to go out on a final “ah f**k it” check in after about a week of investigation. It was all for formalities sake, as again, the guy basically already had won.

When he gets to the quadriplegic man’s neighborhood however, he was quite surprised to see this man fixing shingles on his roof.

At his final court hearing, this f****r gets wheeled in on a bed all dramatically, literally hooked up to IVs and s**t. The Judge tells him to walk over to the stand, everyone’s like wtf but eventually he’s hassled so hard with evidence he just gets up.
Apparently the Doctor, the “victim” (and I believe his lawyers but don’t quote me on that though) were all going to split the insurance payoff and the money from the lawsuit.

Always fun times in Grandpa-land.

#37

Keep watch on the front of the house to see which neighbour was letting their dog s**t on the yard without picking it up. 3 weeks later a homeless guy opens the blast doors. Case closed.

#38

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. Shit retirement.

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

#39

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.

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