25 Of The Most Unforgettable Cases Private Investigators Have Worked On

The internet is a weird and wonderful place where all sorts of unusual information comes to light. Recently, an unexpectedly riveting thread took off online when someone asked, "Private Investigators of Reddit, what is the most bizarre task you've been assigned to?" The wild responses are better than what we find on cinema these days, especially knowing that every lurid detail is very likely true. Scroll below to read about all the most surprising things uncovered by PI's from some wholesome revelations to some unexpectedly heartbreaking discoveries all made in the line of duty.

#1

Image source: you_are_d00med, Lance Reis / Unsplash A couple was divorcing and the wife was sure her husband was sticking random items of hers up his a*s. He was. Anon: So many questions. you_are_d00med (OP): Man I wish I could post video. What you dont realize is I didnt set up cameras in the bathrooms so you gotta picture this dude walking around the house with this toothbrush sticking out of his a*s. Because of course he is naked, I would assume the clothing pushing on it would make it more uncomfortable than it already was. And dude had a semi. I am still scarred from these images. I could never tell if it was bristles out or in tho. Stiflerradi: Why does every thing smell like sh*t?! Ohhh...

#2

Image source: mprovementFar5054, Getty Images / Unsplash 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.

#3

Image source: Which_Algae1157, user32601828/ freepik 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: trackerjakker, Andrej Lišakov / Unsplash 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.

#5

Image source: DoktorInferno, Clay Banks / Unsplash 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. :)

#6

Image source: AvoidableBoat67, Curated Lifestyle/ Unsplash 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.

#7

Image source: questionguy1000, Himanshu Choudhary / Unsplash 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.

#8

Image source: anon, Andrej Lišakov / Unsplash 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.

#9

Image source: anon, A. C. / Unsplash 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.

#10

Image source: Pocketeer1, A Chosen Soul / Unsplash 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.

#11

Image source: CyberTractor, Troy T / Unsplash 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.

#12

Image source: Ghost_of_Sniff 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.

#13

Image source: anon, Nini FromParis / Unsplash 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.

#14

Image source: Kryimsson, Ross Sneddon / Unsplash 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.

#15

Image source: Emotional-Count-8595, Pablo Merchán Montes / Unsplash 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.

#16

Image source: anon, Chinmay K. / Unsplash 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.

#17

Image source: Tee_Hee_Wat, Maxime Gauthier / Unsplash 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.

#18

Image source: valiantfreak 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.

#19

Image source: 44Renegade, Getty Images / Unsplash 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 a*s, 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.

#20

Image source: dcfix, Getty Images/ Unsplash 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.

#21

Image source: BomToody 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.

#22

Image source: mgdmw 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.

#23

Image source: NedTaggart 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.

#24

Image source: RocketCartLtd, Getty Images / Unsplash 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.

#25

Image source: thesecretmarketer, Getty Images 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.