Day in and day out, private investigators rustle through our deepest secrets and our darkest moments—but some skeletons should stay firmly buried in the closet. From cheating spouses who got way more than they bargained for to family feuds turned upside down, here are the most ridiculous cases that ever landed on the desk of private investigators.
1. Weird Revenge
This couple was divorcing, but the wife was suspicious of her husband for a bizarre reason. She was sure that her husband was sticking random items of hers up his butt. So she hired me to spy on him. Turns out she was right. He was doing exactly that. I am still scarred to this day by the photos I took of him in action.
This is a golden example of the kind of thing that only a private investigator would ever get to experience!
2. The Case Of The Imaginary Man
I hired a private investigator to see if a man was real. My dad, we will call him Henry, passed on when I was 15 years old. This was absolutely devastating, especially because my mom and I never really got along. I moved out as soon as I was 18. I asked for all of my important documents, including my birth certificate, but she never agreed to give those to me.
Instead, I took it upon myself to request a birth certificate from the state. I get it, and under the father’s information, there’s a name: “Michael.” When I confronted my mom about it, she said that she made up some man’s information. So I hired a private investigator to see if Michael was real.
Sadly, in the end, she was telling the truth—she just made up a name. I don’t know what’s wrong with my mom.
3. Common Mistake
Whenever anyone mentions a P.I. following someone for workers’ compensation, I always remember this great story. This P.I. came to court with a pile of evidence that this woman who was wheelchair-bound was running around doing errands. He shows all his stuff in court…and then the defense calls the person’s TWIN SISTER who moved in to help her after her accident.
That was, in fact, the person the P.I. had been stalking.
4. Leave No Trace
Not a P.I., but I’m an attorney and occasionally need to hire one to track someone down. We had a case where husband and wife passed on within a few months of each other of natural causes. They had a mortgage with a small balance, but the bank didn’t want to foreclose because it was such a small amount, yet they couldn’t write off that sum, either.
My office was retained to see if the family would pay it off and get title to the house. I did my normal search and couldn’t find any next of kin. Which was weird, because I always can find someone. I spoke to the neighbors, who were friends with the couple for 20 years, but the neighbors knew nothing. They said they felt foolish that in reality, they knew nothing of the departed couple.
The deceased never mentioned family, where they were from, or anything about their past. I reached out to our P.I., who asked for a week to get a report to me. P.I. calls me a week later and says he needs more time, I give it. Finally, the P.I. calls to say there’s no report and he’ll give a discount on the bill. He can’t find them. There is no record of the couple, they simply appeared in the 80s.
In fact, the couples’ first record of existence is the mortgage application. In the 1980s, this couple would have been in their 40s. When I asked for a further explanation, the P.I.’s answer was shocking. He told me, “This is for sure witness protection.”
5. Blood On Your Hands
I was hired once by a man who I didn’t know. He just called me one day saying I saw your ads and I need you to investigate such and such. I was sent $2,000 in the mail, which was way more than my normal asking price. I should’ve known something was up when he told me his rules to follow. No talking about the case to anyone. No contacting the authorities or any other form of law enforcement during this case.
Only contacting the client by phone. No arguing; I could either accept it or not. I thought it was weird at the time, but I wasn’t going to reject $2,000. Day by day it just kept getting weirder and weirder. He kept telling me, “Oh, what’s his daily schedule, where does he like to hang out, does he have any family members or friends that live with him?”
After a week, I was told to stop and that my services weren’t needed anymore, but I was still paid. A week went by and I was sitting on my couch watching the news. What I saw next chilled me to my bones. The guy I’d been watching had been killed, most likely by a hitman, and authorities were investigating the case. To this day, I will never be a private investigator again, knowing I was a part of that.
I still don’t know to this day why he was a target or who called me to investigate.
6. Not What You Were Expecting To Find
I have a story about this. My brother was a private investigator in the early 1990s. He worked for a law firm. I was in my early 20s, and so he got me a gig as a process server. He was working a particularly nasty divorce case. The husband was a Jordanian national married to an American woman. She found out that she was one of several wives that the man had.
She decided that she didn’t want to be the broodmare in the family and wanted out. Also, she worked for NASA. Anyway, my brother was tasked with going into their house, which was in her name, 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, then we went in and got the briefcase. No big deal. We take it back to the attorney’s office and he calls the lady to tell her that he has it. She gives him the combination. He opens it up, and freaks out about what he sees. It was full of technical plans from Boeing for the Apache helicopter.
The attorney just says “Oh my gosh!” He then instantly shuts the briefcase and tells me and my brother to leave right away, so we did. We never heard anything more about that case at all, other than the fact that he contacted the FBI over it. My assumption is that the guy had been plotting some kind of serious attack on a plane. So yeah, things took quite a twist.
7. She’s Seen That Movie Before
I worked for a private investigation firm, though not as one of the detectives. The saddest case we had was a stunning 24- or 26-year old-woman whose 60-year-old accountant husband was suspected of sleeping with his secretary. The secretary looked like she had fallen out of the ugly tree and hit every branch on the way down.
The client hired us to follow him on a night he was “working late.” Sure enough, he and the sleazy secretary left the office on time and went to a bar together. After a few drinks, they retired to her car and we got some pretty revealing footage of them going at it in the back seat. Classy! We gave the footage and report over to the client, who promptly burst into tears and paid the $1,800 or so invoice.
The saddest part of the story? She came back four more times. And each time, he was caught literally with his pants down. He never learned his lesson. We caught him at the secretary’s house, in the car, in the office with the blinds open in the middle of the day, you name it. After about $15k worth of invoices, we actually sat down with her and explained that we were going to stop taking her work.
It just felt cruel to keep taking her money to show her more and more footage of her husband going at it with this ugly woman, over and over and over again. We never saw her again. I hope she took him for all he was worth.
8. Copy Cats
I worked as a private investigator for about a year once when I was much younger. This was a case that I didn’t take, and it 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 on, I closed the office around 5:00 pm. Around 4:45 pm one day, a lady comes in asking all the usual questions. “Are you really a detective?,” “What cases do you take?,” “How much do you charge?,” etc. I spend 10 minutes going through all that with her. This lady seems pretty wound up, which is not unusual, as people don’t typically come in looking for our services 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 to be as detailed as possible. She tells me that someone copied her ideas and that now she’s being followed. I’m thinking, great, a potential intellectual property case.
I ask her to start from the beginning. What were these ideas? She starts telling me about her last gynecological exam. I immediately stop her and ask what this has to do with her ideas being copied. She flips out. She begins screaming about how the doctor implanted a listening device inside her and that this is how they are aware of 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 clearly the listening device!”
I agree that there is a small white dot, but I also 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 knew it wasn’t an electronic device of any kind, let alone one that could capture your ideas and transmit them to vans that were following you around.
She goes on to tell me how the doctor was in on it and that they were taking her ideas and making them into TV shows for Telemundo. This is the part where I tell you that 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. She says 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 payment is contingent on them winning the case. Investigators and all other 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 private investigator.
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 someone seriously mentally ill.
9. Checking Out
The strangest case that my firm ever handled was towards the end of last year. The job was given to us by another agency. It was for that same evening. That is an important detail, as it meant we did not have time to screen the job and get all the details that we would normally ask for. The client suspected that her husband was having an affair with a coworker.
He worked at a hotel in a capacity that I don’t quite recall. We sent two agents to monitor him at work, requiring several hours of effort, all the while putting more on the expenses tab as the team had to keep buying drinks to avoid raising suspicions. The client would phone for updates every few minutes, despite being told not to make contact and that a full report would be issued in short order.
The agents managed to tail the individual until the end of his shift, seeing nothing unusual. They then discreetly followed him home, deciding to give the client a call and confirm that the address he had come to was his house and not that of the coworker that he was allegedly cheating with. The client evaded the question and demanded that the team go back to the hotel.
Confused and irritated, the agents went back and were greeted by the sight of the client, scrambling out of a bush, binoculars in hand, directly opposite the hotel where, judging from the state of her clothes, she had seemingly been for most of the evening. Furious, the agents questioned her. That’s when they found out the bizarre truth. She finally confessed that the man they had been watching wasn’t her husband, but rather someone she had been involved with casually who was no longer returning her calls.
Stern words were had. Management even talked about bringing in the authorities against her. Our firm blacklisted her. She did, however, pay promptly and in full when we sent her the bill. There were many more stories of note from my time in that job. Some funny, and some strange. But that one was definitely the weirdest!
10. Put Me In, Coach
I was a P.I. for five years, I had a few exciting cases. One incident was of a coach who was sleeping with one of the female players. One of the players who was benched hired me to document the coach for sleeping with one of the starters on the team. The coach and the player were careful with how they arranged their meetings.
It took me a bit to document it, but ultimately I got the information. Fast forward a week later, and the papers reported that the coach had resigned to work in the family business…fast forward another week later, the story broke with all the evidence I had collected. I was not named in the story as I had requested not to be.
11. Blinded By The Light
I was hired to follow a woman who claimed that she was completely blind. She was collecting insurance money to compensate for this disability, so of course, the company wanted someone to find out if she was telling the truth. I spent the next day following her around as she drove herself around from store to store in a church van.
12. Something Much Worse
I’ve been a private investigator for 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 she was feeling something different than usual in her relationship and she wanted to know what it was. She strongly suspected her husband of cheating.
So I show up and install nanny cams in her house for the weekend, upon her approval. She shows me where to place them. She works all weekend and this was the best route. Well, three days go by and I collect the footage. I review it and find out that the husband was secretly “touching” his stepdaughter. After seeing that, I immediately rushed to the local courthouse with a copy of the footage and got a court order for the authorities to go and get him.
13. Photo Finish
My father’s not an investigator, but he’s a lawyer and he used to have to look into people who were suing the insurance companies he worked for. One woman claimed she was in a really bad car wreck and was suffering intense leg pain, back pain, neck pain, etc. This was back when MySpace was going strong. So my father Googled her and found her MySpace.
It was filled with recent photos of her clubbing, dancing, and even horseback riding. Needless to say, she didn’t win her case. Now my dad, being a very sheltered individual, did not understand some of the terms he came across on her page—which led to a hilarious moment in court. He had to approach her and he asked: “I just have one question. What exactly does it mean to ‘get crunk?'”
14. Who Knew These Stories Could Be Touching?
I’m a private investigator. One matter which really made an impression on me was where a person had been in a fatal vehicle accident. 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 wife of the worker who’s died in the accident, though his former work colleagues did not know her. Also, the accident took place almost 200 kilometers away from the workplace. When I spoke to former colleagues of his, a lot of them struggled to remember him. This really was so sad.
It left a deep impression on me about what we are once we are dead, if we are not even memories. I did, however, learn that he stayed at a trailer park during the working week. I called that place, but the owner said it had changed hands. He also 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 that the guy would stay near the workplace during the week and then 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. They said it might be so-and-so, and directed me to a house. I went there, and it 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 that the guy ever actually existed after how his co-workers were all finding it hard to remember him. The story broke my heart. He lost his life 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 late Sunday night and traveled back Monday, early in the morning. Tragically, he ran his car off the road and he died. I was able to determine that the lady was genuinely his wife, that he was indeed on his way to the workplace at the time of the accident, that it was his regular route to work, and so on.
I supplied all of this information to the insurer. I rarely ever get to hear what actually happens to a matter in the end, so I can only hope that it was finally settled.
15. Room Service
I’m not a private investigator myself, but I am someone who was confronted by one…and told that it was the weirdest thing he’s ever had to do. A roommate I had in college was a strange guy. This guy came from the other side of the country. 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 private investigator to trail him. Now, living in a college dorm in a part of campus where only freshmen live makes an adult who isn’t janitorial staff stick out like a sore thumb. So, I picked up fairly quickly on the fact that this guy was hanging around the dorms. I thought he was just trying to pick up some freshmen, and didn’t bother him.
A few weeks later, I was walking back from the dining hall, and the guy approached me asking if we could talk somewhere in private. I was weirded out and told him we could talk right here. He told me that he was a private investigator hired by my roommate’s parents to trail him because his parents were concerned, and he wanted to ask me about my roommate’s dorm habits.
We then left for 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. He also liked to hang out at Steak and Shake, play games 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 belongings in the room beside his clothes.
The detective and I both realized that this kid pretty much had no direction or motivation in life, and that 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 ever seen. To explain the kid’s actions, college was the first alone time he’s ever had, and he was savoring it to do 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 about how the mind worked. As soon as that happened, he suddenly became super interested in college. He ended up being a pretty cool guy once he realized that he was not in his parents’ grasp anymore.
16. His Name On The Streets
I once did surveillance on a nurse. She was supposedly so disabled that she couldn’t work. They suspected she was secretly working, though. It was the easiest surveillance I ever did. I arrived. She got in her car ten minutes later. I followed her, with no complication, to a strip club where she went in and began doing her thing.
The club had a posted prohibition on taking 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 entire life and career.
Eventually, it went before a judge. When the judge asked why she was stripping, she just shrugged and said because she made twice as much money as when she was nursing. Her benefits instantly got yanked. The insurance company was happy. But the company lawyer gave me the nickname “Detective Breasts” which, most regrettably, stuck and spread to all of the other lawyers I dealt with.
Worst night of my life, man.
17. Something’s Bugging Him
All right, here goes. After I got out of the Navy, I worked for one of the top private investigator firms in Houston. Because of my electronics background, I’d usually go along on the jobs where we were checking for bugs and hidden surveillance devices. We once 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 1990s, so we didn’t have to worry about burst transmissions or anything like that. 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, then 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 clicking sounds.” Turns out his office phones were routed through the corporate PBX of his client.
So 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 this was legally permissible or not. 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. The Boring Stuff
A college friend of mine was a private investigator. He said that the majority of his casework isn’t tailing people, but serving court notices. He told me of a variety of really slimy ways he’d served people, including wearing disguises, using high pressure tactics, and experimenting with weird social engineering tricks.
He’s out of the field now because he’d had too many close calls. Serving divorce papers or notices of being sued where you have no idea what the state of mind of the person you’re serving is like could easily get interesting to say the least. Let’s just say it’s a field that only people with a high tolerance for danger and excitement should go into.
19. Money Can’t Buy Sanity
I actually have something for this. I don’t have my license, but I work in a P.I. office. I’m the only administrative staff member. It’s basically me and my Vietnam vet boss in a Ron Swanson-April Ludgate kind of situation. A story he told me recently comes to mind. He and his partner were once hired to sweep a house and look for any valuables.
They agreed to the case before knowing the full extent of the damage to the home because the lawyers were willing to pay well and our caseload was small at the time. The home was owned by a man who inherited a large fortune because his father had invested in a little movie that went on to become one of the biggest horror franchises of all time.
The son never worked a day in his life. He had a big mansion out in the boonies. No one ever saw him or his wife because they spent all of their time inside. The home was now empty because he went nuts and killed his wife and their dog. He was serving life in prison and the family’s estate needed the home cleared. When my boss and his partner got in there, they realized how bad it was.
For years, this guy and his wife had been using substances in the house. Every square inch of the mansion was covered in trash. After binging, the two would puke and then just cover the vomit with trash and leave it there. The same went for the dog’s waste. This went on for years. In addition to the puke and animal waste, there were needles littered through the trash.
My boss had to buy hazmat suits to sweep the home and look for valuables. Apparently, there was a ton of diamond and gold jewelry just thrown right in with the filth. At one point, they found a table behind a door that was missed by the forensic crew completely covered in the wife’s blood from where he had done the deed.
They also found an entire room full of kiln and ceramics supplies worth thousands of dollars, all untouched. I guess the guy decided he wanted to become a master potter before quickly abandoning that pursuit to become a creep. They could only access the home through one exterior door that wasn’t blocked. When they eventually walked around the exterior of the home, they found that the guy had purchased himself a shark cage.
As in, he decided he wanted to become a shark photographer, and ignoring the fact that he didn’t live right on the ocean, BOUGHT a shark cage and stuck it in the yard. Eventually, people started to invade the grounds and steal stuff from the home, and one day the shark cage just disappeared. This is the first one that came to mind because it just escalated so much as he relayed the story to me.
It’s hard for me to tell a lot of these stories because of our confidentiality policy. My boss has other crazy stories from working private security for Paris Hilton, Snoop Dogg, and the Girls Gone Wild guy, and we have a few instances of having to serve papers to crazy people. This job is never boring.
20. Instant Karma
When I was an investigator, I was asked by my supervisor to train my replacement. She was in the process of firing all the old blood to pack the office with her friends. It was incredibly obvious that I was next on the hit list, and she wanted me to train a 19-year-old idiot. Seriously, this girl had honestly only found out that Santa wasn’t real the year before, and now she was expected to do a very important job.
But I tried. I could not force her to pay attention to me, so I just explained everything while she played on her phone sitting next to me in my cube. Did not work out well for them. The boss actually chewed me out for not training her when everyone in the small office knew I went over the quirks of the McDonald’s contract with her for nearly half a day.
The salespeople had promised them the world to land the contract, and they had an extremely complicated system for adding new franchisees that were all on a spreadsheet that only I knew how to maintain. Not long after I was let go, we were no longer the official background check company for McDonald’s. That amounted to the firm almost immediately losing about half of its corporate clients.
And that’s about it. Being a private investigator was just a mildly interesting aspect of what was otherwise a typical office job with typical office drama.
21. Crash Landing
My uncle is a private investigator. He got tasked with investigating a collision at an intersection. He found a nearby business that happened to have a camera facing the road at the time, and figured that it would have picked some of the incident up. He collected the footage and got said footage of the collision. And he discovered that his client was definitely in the wrong and caused the accident.
But the video got so much worse. You then see the client attacking 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. The intention was for that to legitimize his story. However, he didn’t count on a camera picking the whole thing up, and so he ended up incriminating himself.
My uncle still got paid for the job.
22. Mr. Veronica Mars
Okay, I have never hired a private investigator, but a friend of mine’s dad was a P.I., and I helped him from time-to-time, kind of like Veronica Mars. The most common clients are trying to catch their spouses cheating, or trying to catch someone committing fraud for worker’s comp. Those who are trying to catch their spouses cheating usually fall into two categories.
There are those who already know their spouse is cheating and who either want definitive proof for themselves or for a divorce, or people who are overly paranoid and have the disposable income to drop a few grand, oftentimes multiple times a year, on their baseless fears. The first ones are not very hard to catch. Unless the affair started at work or with someone they already knew, they likely met their partner on some sort of website.
You would be amazed at what a reverse image search can pull up. A little social engineering/trickery and you can friend them on Facebook and see all the pictures they post. Run it through a program and you can find just about any screen name they currently use. Run that through OK Cupid, Fetlife, AFF, etc. and even Reddit can give you a good head start.
Before things like Google RIS, I would manually search the websites to try and find them. If you know the city they live in, their birthday/age, if they have pets, and have pictures to compare, you can find a lot of profiles of spouses trying to cheat. My friend’s dad didn’t let me do much surveillance, so I mostly searched for things online, but I did spend some time sitting in parking lots, or in restaurants waiting for the person to leave.
I would text him when they did and he would do the actual following. This worked because nobody thought two 18-year-old guys sitting in front of Target listening to 90s alt-rock would be tailing them. People who commit affairs usually don’t worry once they leave the neighborhood they live in. It’s a piece of cake. The people who were paranoid were often repeat customers, as I stated.
They would want to know about every person their spouse talked to. If a wife had a business lunch, the husband would be sure she was cheating on him. If a husband had to work late, the wife was sure he was meeting his mistress. They almost never amount to anything and often we would find evidence that the client was the one engaging in an affair.
Still, they were the client, and it was an easy way to make fairly regular cash, so we never let either party know the client had a side piece. The workers’ comp/insurance ones could sometimes be heartbreaking. Say a dude hurts his back and can’t lift more than five pounds. They would want pictures of him picking up a gallon of milk at the grocery store, as it’s over five pounds.
Or a grandmother putting a grandchild in a car seat. You follow them around enough and you will catch everyone doing something a doctor doesn’t want them to do. Half the time, you would see the pain in their face as they lifted a gallon of milk or a bag of potatoes, but that doesn’t appear in a picture. I hated helping out with these cases.
23. Truth Is Stranger Than Fiction
I’m a private investigator. One time, I was hired by this really famous author to test the security system at his Hawaii vacation home using my professional expertise. So basically, I had to try and break into his house and see if I could succeed—but there was an unexpected twist. Unfortunately, his British caretaker didn’t realize that this was going on, and set his two dogs on me thinking I was a real crook.
I had to escape by hot wiring his Ferrari.
24. Knockin’ On Heaven’s Door
Not a private investigator myself, but I once overheard an unbelievable conversation with one. I was at my friend’s house and he got a knock on the door. The dude said: “Hello, sir, are you X?” My friend replied: “Yeah, why?” The guy then proceeded to explain that he was a private investigator and that he’d like to talk somewhere in private.
My friend said: “Nah, I’m fine just talking here at the door.” The man then showed my friend a picture and said: “Do you know this man? His name is Y.” My friend replied: “Yeah, that’s my great-uncle. He’s vacationing in the Congo right now, why?” The detective replied: “I’m sorry sir, but your great-uncle just passed on from hepatitis.”
The man then elaborated on how his great-uncle, a priest, had slept with some lady of the night while on vacation, and got infected and passed on. Apparently, someone had hired this investigator to track down the poor guy’s relatives and inform them of what had happened. I was in the living room eating pizza the whole time, pretending to be watching TV.
25. On The Job
My significant other had a stalker who would send him flowers. We would come out to our front garden to find notes or gifts—it was a secured area—and once got a glassine envelope left at the front door with strange white powder in it. Nothing happened to us, so it probably wasn’t harmful, but still really weird and frightening.
Then, crazy letters started getting sent to neighbors about how awful I was, that I was a thief or even worse. This went on for a couple of months, so we hired a guy who came highly recommended by our attorney. BOOM. Caught ’em. It turned out to be a married woman who had a bad crush on my husband. We didn’t press charges, but we had the attorney scare the living heck out of her.
That was the end of it. I’m sure this wasn’t the most difficult case he ever had, but he was so quick with the result—it was mind-blowing that our life was put back right so quickly.
26. Not Getting Through
A guy called up my detective agency to ask for Paddy, my late partner. I tell him that Paddy is deceased. The conversation that followed went something like this. Bob: Deceased? Tell him it’s Bob. Me: Bob, Paddy is deceased. I can’t tell him anything. Bob: Sure, okay, whatever. Who is this again? Me: This is Dave. How can I help you?
Bob: Dave, huh? Dave… yeah, Dave, I think Paddy mentioned you. Me: I doubt it, but go ahead. How can we help? Bob: I was just calling to make sure the thing is still on for Friday? Me: What thing? Bob; The thing, you know… Me: I don’t know, Bob. What? Bob: Well yeah, I know you don’t “know”, but is it on? Me: Bob, I have no idea what you are talking about.
Bob: Okay, I get it. Of course you don’t know. But, all I’m saying is, we’re good, right? Me: We are not good, Bob. I don’t know what you are talking about. Bob: Of course. Got it. No idea. Great. Friday? Me: Bob, Paddy is no longer alive, so whatever you think is happening on Friday is not happening. Understand? Bob: Perfectly. Tell him I will see him then.
He then called back later and again asked for Paddy. That conversation went like this. Bob: I was told to ask for Paddy. Me: Paddy’s passed. This is Dave, how can I help? Bob: Hmm, I was told to ask for Paddy. Me: You did that, and I told you that he has passed. So can I help or not? That’s when I finally learned what the heck he was talking about. He says, “Well, okay. Then I need to disappear.”
Me: What do you mean, disappear? Like, from your girlfriend or from the Feds? I literally have no idea what you mean. Bob: No. Like, really disappear. Like, as if I don’t exist. Me: I don’t know what movies you have watched, but there is no way to just disappear unless you have a ton of money and a body to use as a decoy.
I just made this line up on the spot to try and get the guy to shut up. But to my surprise, things got even weirder. Bob: I have three-million in cash. The body is no problem. Can you help or not? Me, not knowing what to say anymore: I can’t talk about this on a cell phone. Click. And the guy never called back. It left me wondering what the heck this was all about.
I later found out from tracing the number that the call had been from a real estate investor who was being sued for millions in back taxes by the government—and that’s not even the craziest part. According to the newspapers, that same man “lost his life” in a private plane crash about a week after the phone call. Pretty suspicious, huh?
In case you are wondering, I am no longer in this business and the firm itself no longer exists.
27. Can You Paint With All The Colors Of The Wind?
Ah, finally something I can share! A few years back, I accidentally became the owner of a detective agency. I intended to just be an investment partner, but the owner and actual P.I. passed on shortly after I made my investment and lo—I now owned a detective agency. After quickly getting the various licenses, etc., I just started taking cases.
The entirety of what I knew about how to be a P.I. was from various TV shows, movies, and books. For cases, I would just rely on random people whose life has become so bad that they decide calling a P.I. is the next logical step. Much later, I learned that normal P.I.s never take these so-called “domestic” cases because they are always a huge mess.
Real P.I.s get almost all of the work from lawyers and hire off-duty authorities to do all of the leg work. As a result, I had a TON of crazy cases. This is the best one. Guy calls me to help catch his neighbor who is knocking over his trashcans at night. We set up a small night vision camera to catch the guy. Watch the video the next day—it is the wind.
The client freaks out, says that his neighbor could have had an invisibility field or could have been moving too fast—like the Flash—to show up on camera. Wants to pay us thousands of dollars to rent a heat-seeking camera or one that can shoot thousands of frames per second. It turns out lots of crazy people call P.I.s to investigate the TV controlling them, alien abduction, etc.
28. Let It Go, Dude
My ex-husband went off the deep end when I left him three years ago, despite the fact that he was cheating on ME every step of the way. Anyway, I moved 1,000 miles away and began to restart my life. One day, about a month after leaving him, I checked my mail and saw that I had a huge, heavy envelope in the box. When I opened it, I was horrified.
It was photos of me doing allllll the activities of my daily life, but the photos were clearly taken from afar, and without my knowledge. Immediately, I contacted my attorney. It turns out, my ex was hoping to catch me with someone else, because he wanted to try to sue me for abandonment. It was awful, and it took me a long time to feel safe and secure in my new home.
29. Beach Bummer
We had to follow this cheating husband to the beach in Florida. I got paid to go hang out in a nice beach town all day and night. Didn’t get a lot of sleep, though, thanks to having to be up gathering video evidence after they went to bed, but it by far beat the normal jobs. What’s crazy is, the daughter was able to catfish her father and get more evidence.
He also had a stupidly easy password on Match.com, so we could see everything he was saying and planning. Of course, what’s sad is people cheating, and they have to know their partner knows they’re cheating, but they keep doing it even though their partner asks for a divorce and they refuse. Usually, the cheater is better off financially if they’d go ahead and leave.
No one is happy but they just keep going. What was infuriating was just straight-up busting someone with perfect evidence of infidelity, and then the client goes and takes them back and ruins all of our work. The law is infidelity evidence only counts if the offended party does not take them back or sleeps with them, so it’s annoyingly fragile in these dramatic relationships.
30. She’s Seen It All
My wife was a P.I. Not a lot of research, mostly documenting insurance scams. The last case she ever worked, she was staking out a house, trying to get a man who was claiming not to be able to work because of his car accident, doing stuff he says he can’t do. He opens his front door, and she starts videotaping, hoping he’ll start doing yard work or something.
Instead, he pulls out his you-know-what and starts going to town on himself on his front step for a few minutes before walking back inside. The tape became legendary comedy material in the office she was working at.
31. Hitting The Big Time
I guess I can contribute. I’m keeping this intentionally vague just because of the nature of things. My family member is a P.I. He was working a case a few years back. Hired to catch a spouse cheating, so normal case to have. Well, this initially typical case ended up kind of turning into a case dealing with a hitman being hired against the client by the client’s cheating spouse.
I deactivated my Facebook for a while until things blew over at the suggestion of the P.I. and law enforcement, since the P.I. and I share a family name. I was happy to oblige. I was a bit scared because of the hitman and all. Kind of funny, but I didn’t realize it was made into a kind of a TV special thing until we were watching the show over a year later and I noticed that the story seemed a bit familiar.
Then it showed some clips of the cheating spouse’s home and I recognized it. I sometimes traveled with my relative to help with the case. Plus, there was a good taco place down the road, so I wasn’t going to turn down a trip to get tacos. The TV special was a bit vague on how they were able to connect the hitman to the cheating spouse in court, but really it was due to evidence that the P.I.—my family member—collected and turned over.
They wanted to include that, but the P.I. relative did not want to be on TV.
32. Terrible All Around
I once handled the case of a kid that was so gruesome, it’s impossible to forget. He’d accidentally fallen into a raw sewage tank and two employees dove in to try and save him. Sadly, not only did the kid have to spend his last few moments on Earth drowning in a pile of human waste, but both employees who wanted to help developed serious health problems from the exposure to the raw sewage.
One of them ended up taking his own life, and the other had chronic health problems from it.
33. Family Matters
I’m not a private investigator, but I know someone who was a junior detective. This one case he had was an absolute mind-bender. So this guy had been cheating on his wife (the client), with her brother. Except—she claimed she didn’t have a brother at all and grew up as an only child. So naturally, they were really curious to find out who this “brother” of hers was.
When they questioned the husband, he said that the guy who claimed to be his wife’s “brother” said that “We’ve known each other for so long” and “I grew up with her” and all that jazz. At first, my friend assumed it was probably a long lost brother or something, but then when the husband was asked to describe the guy—get this. He described the wife’s father.
According to the wife, her father wasn’t there during her wedding and was replaced with her uncle instead. The husband hadn’t met him before. He was cheating on his wife with her father! Absolutely wild.
34. Save The Drama For Your Mama
My family has hired P.I.s on three separate occasions. All three of them found massive amounts of infidelity, with two of the three uncovering secret families. great-grandpa died, turns out to have had three wives simultaneously. My grandpa hired the P.I. to figure out the details and clear up the messy inheritance it caused.
Oddly enough, grandpa was on great terms with his newfound half-siblings for the rest of his life. Then, my uncle traveled a bunch to Mexico for work, so my suspicious aunt hired a P.I. to trail him. Turns out, he had an illegitimate family in Mexico. It caused a huge inheritance pain in the butt AGAIN when my uncle eventually died of natural causes.
But that wasn’t even the end of it for my crazy family. My cousin was married to a professional baseball player on the East coast. My folks suspected he was a cheater and hired a P.I. to trail him, turns out to be a rampant cheater for sure, divorce followed shortly. To this day, he’s considered an un-person in my family, and no one will tell me what his name was or what team he played for.
35. I Spy
It was one of the last cases that I ever worked on. It was for a child custody and paternity case. This case was the one that made me rethink what I was doing with my life, and I got very disturbed by what I was asked to do. In other words, this is the case that made me stop being a private investigator. Here’s what happened.
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 of dollars on the case for us to make sure there was evidence to support his claim. The icing on the cake was when my case manager told me that the client wanted video evidence showing 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 nine-year-old playing with his toys. I couldn’t have possibly 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.
36. The Curious Case Of The Woman In The Night-time
Currently studying behavior analysis. A middle-aged woman, presumably between 45 to 50, was found dead behind a dumpster around a local bar in the middle of December. She was wearing a skirt that was pulled up to her waist, and leggings that were pulled down, and torn in multiple spots. She also had abrasion around her buttocks, the heels, thigh, and wrists.
At first, the investigators are thinking that they had a sinister case on their hands. However, certain things were not adding up. Even though it was mid-December, that particular bar was fairly populated, and thus, someone should have reported at least hearing a woman in distress, as the dumpster was near the parking lot of the bar.
Also, the abrasions on her buttocks were rather strange, as if someone had dragged her across the cement floor. After some investigation, they found no traces of physical evidence that suggested there was an attacker. No saliva or hair. Later, it was revealed that due to loneliness of losing her husband and her daughters having left home as adults, this woman went to the bar to meet a potential new partner.
But, she had gotten carried away drinking. Once outside in the freezing cold, she wants to take a leak and hides behind the dumpster. While doing so, she is slowly suffering from hypothermia due to the cold winter wind and lowered body temperature caused by the alcohol. She begins feeling hot (due to paradoxical undressing, caused by hypothermia).
As a result, she presumably strips off her jacket and other pieces of clothing. At this point, the hypothermia is really getting to her badly and she begins slowly losing consciousness. While laying on the freezing ground, with her skirt pulled up and leggings down, she begins convulsing, which leaves abrasions on her body.
All this left behind a curious scene that appeared as if she had been taken advantage of.
37. Flash Photography
Doing a standard pre-employment background check on a guy, I learned that he had been found guilty in a harassment case. I didn’t have all the case details at that point, and the applicant denied that it was him. I 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 that it was him, but claimed that it wasn’t as bad as it seemed. He pulled out the court transcripts from the trials. Turns out he flashed a 12-year-old girl on the beach and said “Ever seen one of these before?” Suffice it to say that when I reported my findings back to my client, this fellow did not get the job…
38. Sister, Sister
Someone I worked with was retiring and was going to spend her days being a P.I. which was pretty cool, I thought, and I asked her if she could help me with something that had been bothering me since I was 12 years old. My father, who was living across the country at the time, flew to see me and my brother just for a day.
I would find out years and years later that the reason he did that was that he had cancer, and wasn’t sure if he was going to die or not. My dad doesn’t talk about anything. He’s the weirdest guy. Like, ever. Which brings me to the conversation we had that day. He told us that before he met our mom, he had knocked up this girl he worked with, and she kept the baby.
He had no relationship with her at all or her mother. He claims he wanted to, but she didn’t want anything to do with him. But knowing my dad, I’m pretty sure that’s all a load of hogwash. I bet he just bailed. He said he just wanted us to know that we had a half-sister, and then he just left. Like I mentioned before, weird guy.
So it was always in the back of my mind that I had a half-sister out there somewhere, and I was always curious about her, but my dad never brought it up again the few times a year he bothered talking to me at all. So I didn’t know how I could find her. I tried searching the internet a few times, Facebook and things like that but I never got far.
So fast forward to when my co-worker tells me she’s going to be a P.I. It hit me! I told her the story. I asked her what she would need to figure out who she was, and she said just my dad’s name and date of birth, and she might be able to come up with something. Not even two weeks later, my amateur P.I. buddy is messaging me on Facebook and sends me to the woman she believes is my half-sister.
I remember it exactly because at the time I was out at a bar with my step-sister, and when we saw the photo we both looked at each other and were like “That’s gotta be her!” I just had a strong feeling. So, in the time from when my dad told me about her, to the time the P.I. had found her (14 years?) I’d moved back to where I was born.
From what I could see on Facebook, my half-sister lived within 30 minutes, had just given birth, had a husband, and she just overall seemed really happy and cool! I was so happy for her. I reached out to her. Sent her a message on Facebook explaining who I was. I had no idea if she knew about me or not. So I told her I didn’t want anything.
I just wanted her to know that I knew that we probably had the same dad. Then I waited, wondering if I should be upset about something that I never had in the first place. It took her almost a year to respond. The message went to some folder and she never saw it, but then she did! She confirmed that she was my half-sister!
We exchanged a few messages back and forth before finally meeting for lunch one day. It was a little awkward at first, but we’re both a little awkward. And that’s actually what was so crazy to me. The weird similarities we had with each other. The whole thing has been kind of surreal. Since then, we’ve met up for lunch a few different times, and went to a concert together.
I’ve never told my dad that I have a relationship with her. I told my half-sister that if she wants me to tell him anything, then I will, or put them in contact. But other than that, I don’t see why I would. And he missed out big time, as far as I’m concerned. Because she’s awesome! I wish I saw more of her. In fact, I’m going to text her right now and see if she’s free for lunch.
39. Survey Says
As a college student, I worked for a private investigations firm and shadowed a wealthy retiree for days on end. His kids were “concerned” that he might remarry and cut them out of the will, so they hired us to report on his activities. He was having a heck of a good time. Golf, dancing, drinking, and hanging out with many widows, too.
I needed to approach him at one point and pretend to be conducting a “survey.” He didn’t know that I’d been following him for days on end. He cooperated nicely, answering all my silly questions. He had no clue that I already knew everything about him. But once I talked to him directly, I really started to like the guy and wanted to tell him the truth. But I didn’t do it. I turned in the report.
I have always felt both guilty and creepy about being so duplicitous towards this guy.
40. Mistaken Identity
I have had some ridiculous clients, but this one tops them all. A guy calls to ask for Paddy, who happens to be my late partner. We tell him he is dead. The conversation that follows goes like this: He says, “Dead? Tell him it’s Bob.” I say, “Bob, Paddy is dead.” He replies “Sure, ok, whatever. Who’s this?” I say “This is Dave. How can I help you?”
He goes on: “Dave huh? Dave…yeah, Dave, I think Paddy mentioned you. I was just calling to make sure the thing is still on for Friday?” I say, “What thing?” He’s all like, the thing, you know. Super mysterious. I keep telling him I don’t know. He then says, “Well yeah, I know you don’t ‘know,’ but is it on?”
I flat-out say, “Bob, I have no idea what you are talking about.” He replies, “Ok, I get it. Of course, you don’t know. But—all I’m saying is, we’re good, right?” I say, “We are not good Bob. I don’t know what you are talking about.” He goes “Of course. Got it. No idea. Great. Friday?” By now I’m losing it. I tell him, “Bob, Paddy is dead, so whatever you think is happening on Friday is not happening. Do you understand?”
I couldn’t believe it when he replied, “Perfectly. Tell him I will see him then.” The weirdest thing was, this kind of thing happened again. Different call, also asking for Paddy. After the guy says he was told to ask for Paddy, the conversation went the same way. Then he told me he needed to disappear. I say, “What do you mean, disappear? Like, from your girlfriend or from the Feds?”
I literally had no idea what he meant. He says, “Really disappear. Like, dead.” I tell him there is no way to disappear unless you have a ton of money and a body. I made this line up on the spot, by the way, just to shut the guy up. Then he says, “I have 3 million in cash. The body is no problem. Can you help or not?” That’s when I knew that Paddy had been into some really bad stuff.
I told him I can’t talk about this on a cell phone. Hung up. Never called back. Later found, from tracing the number that called me on, that it belonged to a real estate investor who was being sued for millions in back taxes from the government. But that wasn’t even the most insane part. He perished in a private plane crash about a week after that call…
41. Chasing Its Own Tail
A client once hired me because she wanted to know why her dog was getting fat. I shrugged, and took the job even though I thought it was a pretty weird assignment. So I shadowed the dog the next day. Turns out the dog was getting fed by almost every stranger it encountered while wandering around outside during the day.
42. As A Matter Of Fact
One of my clients called into the office wanting to find the culprit behind, get this, “indiscriminate fecal matter disposal” on her porch. So I did the usual routine. I scouted out the neighborhood and asked people questions about seeing anything at night or any other suspicious activity. A lot of people laughed in my face.
43. Follow The Leader
I once had an interesting case in Texas. I was following a guy who supposedly had a serious back injury. Well, I caught him in the act—but not necessarily in the way I expected. I watched him go to the mall, where he met up with a woman that was not his wife. I followed them around as they shopped, and then they headed back to his vehicle where they proceeded to fool around 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 video to the client. The girl was pretty attractive, too!
44. Space Invaders
I had a case referred to me by an attorney I worked for. It involved 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 to the key. Heck, 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 had been there.
A couple of days go by and she calls. I go by and get the tape, since this was before digital recordings. I check the footage out. There’s nothing on it but her. I meet her to tell her this. Her reaction made my blood run cold. She says, “Oh, 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 what the best course of action might be 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!
45. Strong Man
I worked for a private investigator company that mostly handled workers’ compensation cases for insurance companies or other employers. I was assigned to a case in Seattle where a guy was claiming an upper back and shoulder injury. After a few hours on site at his house, he pulls up in a truck and proceeds to empty the truck bed of landscaping equipment. Alone.
After he has put everything away, he walks over to the side of his neighbor’s house, pulls out a piece of the siding of the building, withdraws a pipe, and smokes it in front of me. All on camera.
46. Strange Brew
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 terrible blizzard. I didn’t end up getting there till 7:40. I go to my boss, who says he already fired the guy before I arrived.
What the heck, man? What if he had lashed out and what not when I wasn’t there? His reply was that he didn’t, but that he wanted me to still stick around just in case. So I sat there for four hours drinking coffee on double time, which was great until I had to file the two-page report on me drinking coffee. But yeah, I can’t complain about getting to drink coffee for 35 bucks an hour.
47. Battle Scars
My RA during my sophomore year of college was a part-time private investigator, and he loved to brag about it to the new coed underclassmen. A few weeks before spring break, he showed up with visible bruising and two black eyes. Apparently, some guy he had been following to try and catch in an affair had gotten a hold of him and beaten him to a pulp.
48. No-Tell Motel
I’ve worked on a few bizarre cases over the years. There was one interesting workers’ compensation case from last year. I was told to get film of this older lady who had supposedly been on total disability due to a severe ankle injury. Seems cut and dry. But she lived in a motel in the middle of nowhere in rural Pennsylvania.
The motel was called “Johnnie’s.” I looked up the place online and found reviews of it on Google. There were really lousy reviews, including one that said the place was mostly run by the owner’s son, who was a substance user, and would ask people who stayed there if he could buy any prescription medication from them. That isn’t sketchy at all.
So I show up to this “motel,” which looked like it hadn’t been renovated in 40 years. It was a small motel that had about 14 rooms. I have no idea what room the person I’m supposed to find is in. I figure I should talk to someone at the front desk. Turns out there is no front desk. The office part of the motel looked boarded up.
But next to it was one of the motel rooms, and in the window of the room was an “Open” sign. On the door, there was a sign that said “office” and instructions for long term customers of the hotel on where to drop their payments. There was a doorbell. I rang it and waited. The guy who opened the door looked exactly like Kenny Powers from Eastbound and Down.
He was wearing a Ninja Turtles t-shirt and Hawaiian shorts. He tells me to come in. I walk in, and what I walk into is just a room with one desk. Nothing else. There was shaggy carpeting, some really dark colored walls, and a lava lamp on the desk. I realize that this was the owner’s son, Johnnie Junior. I give him some fake story about how I’m an insurance adjuster looking for this lady.
He then replies: “Oh, Mary? She lives in the room next to me, want me to go get her?” This is a problem because I have absolutely no backstory on what to tell this lady. She was represented by an attorney and likely knew a private investigator might be looking for her. I tell him no, and that I just needed to confirm that she lived here. I then bolted.
I parked in the parking lot with a view of the room that Johnnie Junior had pointed at. A couple of hours go by, and then some old guy standing near my car starts getting stuff out of his car. Johnnie Junior walks out and starts talking to him. I realize the older guy is Johnnie Senior. They are literally standing right next to my car and I can hear everything they say.
What proceeds to happen is they start talking about me. Well, at least about the “insurance adjuster” who had visited earlier. Johnnie Senior, having seen some stuff in his day, immediately says: “That wasn’t an insurance adjuster, you idiot, that was a private investigator! Insurance adjusters don’t work on Sundays!”
He tells Johnnie Junior to tell Mary to watch out because an investigator might be in the parking lot. My car is tinted. I think I’ll be fine. Not so fast. The parking lot I’m in is shared with a diner. The owner of the diner comes out and starts talking to Johnnie Senior. Apparently, I had parked in front of a shed that the motel cleaning staff used.
Johnnie Senior now starts talking to the owner of the diner and asking her if my car belonged to any of her employees or any of the people in the diner currently. She says she’ll ask around, and she leaves. Johnnie Senior then goes into one of the motel rooms, where apparently he lives. He constantly stands in the doorway looking at my car. I leave as soon as he looks the other way. But I still got what I came for.
I came back later in the day and successfully get film of the lady I was supposed to watch. She was totally faking her injury. Johnnie Junior and his girlfriend actually came out a couple of times to try and figure out what car might be an investigator’s car. But because they had seen my car earlier that day, they didn’t seem to suspect it as suspicious.
49. Woman’s Best Friend
An older gentleman hires the investigator, as he believes his young and attractive wife is cheating on him. The investigator follows the wife for an extended period of time but does not discover any liaisons. To make a long story short, the investigator eventually makes a disturbing discovery. The young wife had been sleeping with the household dog. Yes, you read that right.
Apparently, the wife had been extremely emotionally frustrated because she wasn’t getting any from her over the hill husband, but she couldn’t bring herself to actually cheat on him. Enter the dog…
50. I Saw The Light
I did surveillance for insurance cases for a short time. We would usually just be assigned to follow someone for a couple of days, unless we found something that warranted more time. On my first day watching this one guy, he leaves his house about seven hours into my eight-hour workday. I follow him out of the neighborhood, then out of the town, then onto the highway…
I start wondering where he could possibly be going to. Eventually, he pulls into the downtown area of the nearest metropolitan city and heads 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 my car over to the valet.
I 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.
51. Being A Jerk Doesn’t Pay
My boss once hired a private investigator. He never told me, but I was snooping around the network one day and came across a document that was a chain of cut-and-pasted emails between the boss and the guy he secretly hired. I worked for a playground design and construction company. Very small, and the boss was an absolute jerk.
He may have been bipolar, because he would be happy one minute and then the tiniest problem, like a slide being a slightly different color 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 for 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 United States, so this is probably very uncommon here. The detective went to a construction site and talked to a bunch of the workers.
He returned a report that stated that the workers were cooperative, that they did not appear to be foreign, that they spoke English very well, and that they even showed him their driver’s licenses. He left totally satisfied that the workers were legitimate Australian citizens. And then, inexplicably, my boss got mad at these results and refused to pay the guy.
The rest of the document was the detective arguing that he did the work and should be paid for it. The bill was for at least a few thousand dollars, I think. My jerk boss wrote him back and argued that he just knew that those guys weren’t allowed to work and that if the private investigator couldn’t prove that, then he wasn’t a very good investigator and didn’t deserve to be paid.
52. A Graceful Excuse
I was once asked by a lady to investigate her husband because she thought that he might be cheating on her. Apparently, he used to come back late at night with the smell of women’s perfume on his clothes. So I tailed him to see what was really going on—that’s when I found out a twist that even I never could’ve predicted. Turns out, he was taking dancing classes and didn’t want to tell his wife.
53. Taking Out The Trash
A few years back, I accidentally became the owner of a detective agency. I intended to just be an investment partner, but the owner and the actual detective both passed shortly after I made my investment. So, all of a sudden, I now owned an entire detective agency. After quickly getting the various licenses and all, I just started taking cases.
The entirety of what I knew about how to be a detective was from various TV shows, movies, and books. For cases, I would just rely on random people whose life has become so bad that they decided to call a private investigator was the next logical step. Much later, I learned that normal investigators never take these so-called “domestic” cases because they are always a huge mess.
Real investigators get almost all of their work from lawyers, and hire off-duty officers to do all of the leg work. As a result of my not knowing this, I had a ton of crazy cases. Practically several TV seasons’ worth of them. Here is one ridiculous one that I will never forget. This guy calls me to help catch his neighbor who is knocking over his trash cans at night.
We set up a small night vision camera to catch the guy. We watch the video the next day. The video reveals that it was just the wind. The client freaks out, and says that his neighbor could have had an invisibility field or could have been moving too fast to show up on camera, “like The Flash.” He wanted to pay us thousands of dollars to rent a heat-seeking camera or one that can shoot thousands of frames per second.
Turns out lots of crazy people call PIs to investigate the TV controlling them, alien abduction, etc.
54. A Familiar Face
Being a P.I. is super interesting in a lot of ways, but it can also ruin lives—your own included. A couple of years back, I was investigating something on Adult Friend Finder and discovered pictures of a close friend from high school who I had a massive crush on. Her husband had uploaded pictures of her, including her face, to try to meet women.
A lot of guys will do this, use pictures of their wives to try and set up a threesome, and then tell the other girl the wife wants him to meet with her first. My friend had no idea they were on there. It ruined her marriage and her friendship with me. I didn’t care about what she and her husband did in the privacy of their own home, but she couldn’t look me in the eye after it.
We hadn’t been close after high school but it messed with sort of future friendship, which makes me sad. When I did tell her about finding that stuff, she admitted that her husband had cheated on her in the past, before they were married. I have no idea why she stayed with him.
55. Magic Touch
I had one hired against me, and they found out everything. Tattoos that aren’t visible normally, the address I lived at in a different country, medical records from an accident that happened six years prior, so many random things that aren’t publicly available. It really, really creeped me out. Those people are like magicians.
See, I’m a bartender. When I was buying my house, the loan I was applying for switched mid-way through and I needed money to pad my bank account. One of my well-off regulars loaned it to me, complete with a contract and a pay-back date. However, he drafted two, and crumpled one up and tossed it. This came back to haunt me.
His wife found it and hired a P.I. against me. She confronted him about it. He told me the next day that she was listing off all the facts the detective told her about me. None of which the regular previously knew. He didn’t even know my age at the time, so there’s no way he knew all that other stuff.
56. When The Cat’s Away…
Last year, when I was 17, I pretended to be a private investigator just for fun. My neighbor gave me ten dollars to go look for his missing cat. I guess he just wanted me to have some fun and I was just fooling around. I was pretty sure I wouldn’t find anything. But darn did I ever find something. A very big something.
At the bottom of my street, there was an old abandoned retirement home that had closed a couple of years after I moved in. I went there first and found a blood trail leading into the place. There wasn’t a lot of blood, but just enough that it could have been the cat’s blood. Case in point: It turns out the building was being used for an illicit substances operation.
After seeing that, I almost pooped myself because I was only going into the whole P.I. thing as a joke. I anonymously tipped off the authorities, who raided the place. Apparently, one of the guys accidentally attacked the cat, who started to wail loudly, and he was scared people would come to investigate. He couldn’t bring himself to end the cat’s life, so he dragged it inside and forgot to clean the blood away.
It was one of the most thrilling yet terrifying things that I had ever gotten myself into. But hey, at least the cat lived and my neighbor got her back!
57. Bowling For Dollars
My firm had a bad faith insurance case several years ago. A guy had gotten hurt at work. He claimed he was disabled because he hurt his back, and could not lift anything or really engage in any type of physical activity. His disability insurance carrier failed to handle the claim and pay him what he was owed. There was a potential for relatively large damages.
In fact, the carrier filed in the court case what is known as an Offer to Confess Judgment. It’s a way of agreeing to let judgment be taken for that amount. The plaintiff can accept the offer or reject it. However, if he rejects the offer, he is responsible for the defendant’s attorneys’ fees if the verdict ends up being less than the amount of the Offer to Confess Judgment.
The offer, in this case, was $ 750,000.00 He rejected the offer. A few weeks later, our P.I. found out that the plaintiff bowled every week. The P.I. got a video of the plaintiff bowling and copies of his score sheets going several years back through the date of the accident. It was clear he really was not disabled. He also found that the plaintiff had been in a car wreck and was making identical injury claims to the other driver’s insurance carrier.
We filed a motion with the court to dismiss the lawsuit based upon perjury. The court set the motion for a hearing, but before that happened, the plaintiff dismissed his lawsuit. Smart choice.
58. All In The Family
My mom’s biological father was basically cut out of her life when she was 3-4 years old. She never really knew him and my grandmother tried to keep his existence limited after she married another man—the one that I consider my grandfather. My mother knew basic information about her biological dad but no history about his life, medical history, how he looked, etc.
After my grandfather passed on, she began looking into it more and hired a P.I. Ultimately, after sending many emails to random people with little luck, she was able to get in contact with his first cousins. She discovered that both her biological father and his brother, whose children she had found, had died but her aunt and one of her sons lived one county away.
I ended up going with my mother to meet her cousins. It was really weird. She has certain features that didn’t come from my grandmother that were clearly present with her cousins. It was a funny experience to meet them and talk about their uncle—my mom’s father. Apparently, her father was very much of a jerk and ended up dying somewhat alone.
The cousins weren’t close to their father either. I think my mom still gets emails from them every so often to be kept in the loop with some family happenings.
59. Somebody’s Watching You
My ex hired a P.I. against me to find anything and everything he could to try and twist it around and make it look like I was an unfit mother. He was trying to win a custody battle. The P.I. sat outside of my house, taking pictures and videos. He followed me in public and took videos and pictures. He gleaned anything he could from social media.
My friend tagged me in a post that said something like, “Drinking Friends, ASSEMBLE!” and that was presented as evidence that I was an alcoholic. Heck, I am the DD more often than anyone! We ended up settling before the trial came, so thankfully this folder of photos of me attending a street dance, *gasp* dancing, and printouts of any references to alcohol made on Facebook did not get presented in open court for me to defend every single action.
Unfortunately, he does present this “book of shame” to parent mediators, counselors, and anyone else he thinks should believe that I’m an alcoholic horrible mother. This left me with lingering paranoia and distrust, no surprise. I have had to leave public venues for fear that I’m being watched. Nothing has damaged me more than this.
60. Framed By Frame
I was once hired by this Seventh Day Adventist lady in an abusive relationship who wanted to divorce her husband, but apparently needed the husband’s permission according to their religious customs. The husband refused to give her his permission. So she wanted us to hire some woman to seduce him, get it on video, and then mail the tape to the church leaders to show that their marriage was broken.
61. Cheater, She Wrote
An old professor of mine had a wife who was a P.I. She was about five feet tall, cute and plump, with gray hair, big cheeks, and a sweet smile. She looked like a sweet old lady who could be the best grandma ever. This is exactly why she was an amazing P.I. No one ever saw her coming, if you know what I mean. She could get in and out of buildings with the information she needed by chatting people up and getting them to spill the tea—or even hand her copies documents needed.
They should really make a movie about her.
62. More Than He Bargained For
One woman I was hired to investigate was married to a guy who made a decent living. He wasn’t mega-rich, but he likely made around $250K a year. He started to suspect his wife was cheating on him, so we tailed her for the weekend. It was only one weekend, but we quickly discovered that she was selling herself on Craigslist and Backpage.
We caught over 13 men coming in and out of her motel room that weekend and found her ads online.
63. Holier Than Thou
There was Seventh Day Adventist lady in an abusive relationship who wanted to divorce her husband, but apparently she needed the husband’s permission, which he won’t give her. So she wanted us to hire a “lady of the night,” if you get my drift, to seduce him, get it on video, and then mail THAT to the church leaders to show the marriage is broken.
64. A Real Mastermind
I had a man who was serving 20 years for hiring a hitman (who happened to be an undercover cop) to kill his friend. In prison, he came into some money and hired me to prove he was innocent. His brilliant plan to do this was to have us tell his friend that he better recant his testimony, or else our client would use his new money to hire a hitman to kill him “for real this time.”
This genius told me this plan on a recorded phone call from the correctional facility.
65. Guilty As Charged
This crook was serving 20 years for hiring a hitman to target his friend. Unbeknownst to him, the hitman happened to be an undercover officer. In the slammer, he came into some money and hired us to try and prove that he was innocent. His plan to do this was to have us tell his friend that he better recant his testimony or else our client would use his new money to hire a hitman “to do it for real this time.”
This genius told us this plan on a recorded phone call from the facility he was in.
66. Denial Isn’t Just A River In Egypt
I once got hired by a wife who wanted to see if her husband was sleeping with his secretary. We followed them, and recorded them going into his single-bed hotel room at approximately 10:20 pm after a nice dinner out. I then recorded them leaving together the next morning at 8:00 am. When I brought the tape back to my client, she was very upset—but what she said next was jaw-dropping.
She said that the video proves nothing, as they could have just been working late…
67. It’s Not What You Find, It’s What You Don’t Find!
I’m a private investigator. I’ve been hired to go out on many interesting cases over the years, but the most shocking one I’ve ever had was the one where I was hired to investigate a husband because the wife was suspicious of all the times he had to “work late,” only to find out he really was working late. It was the only time where the person wasn’t cheating.
68. It’s Electric
I once went out on a case that involved a teenager who had opened a high voltage electrical cabinet. He stuck his arm inside and his metal wristwatch melted into his wrist. He almost lost his life in the incident. His family was trying to sue the power company, claiming that the barbed wire fence enclosure and the double lock-sealed cabinet was “inadequate” protection.
They wanted their kid to be compensated. I don’t know how this case ended up. I just turned in my reports and moved on.
69. Lick It Up
I’m a private investigator. Someone wanted to know what their cat was up to when they were working, so they paid me to tail it. I don’t like wasting my time, but work is not always easily available in this field, so I took the assignment. Turns out the cat just walks around the streets, licks itself, and climbs trees…
70. Reeling Them In
I was hired by a private investigation firm to work at a company that was having a problem with workplace harassment. He wanted me to dress scantily and report anyone who verbally or physically came on to me. I was a teenager at the time, and I really didn’t understand what being hired as bait could mean. I was used by that jerk.
71. Fire And Brimstone
I’m a private fire investigator. I once had a guy tell me that the church across the street would gather in the street and group-pray that his house burned down. Turns out, that wasn’t actually what happened, go figure. In actuality, the tenant who was staying there had a boyfriend who actually did the burning. It was NOT Jesus, as one church member claimed.
72. Power Napper
I used to do background checks for employment. The funniest one was a guy who was working for a large provincial hydro company and was trying to get a raise, so they wanted me to look into him. He relied solely on GPS. He had to drive to a remote site a few hundred kilometers away. The next day, the crew were waiting on him.
Finally, the foreman calls to see when he would arrive. The applicant answered sleepily and said his GPS signal stopped about 250 km in and he just turned around and went home. Didn’t call anyone, use a map, just went home. He also used to take a little boat pretending to survey sites. Several times he was caught sleeping, just floating around in the boat.
The most surprising thing? He got the promotion he was seeking.
73. Just A Little Innocent Fun
I got hired by a wife to see if her husband was sleeping with his secretary. We followed them, recording them going into his single-bed hotel room at 10:20 pm after a nice dinner and leaving together the next morning at 8 am. I think that it’s a slam dunk, but the wife’s reaction was heartbreaking. She suddenly went into total denial. She told me it proved nothing and that they could have just been working late.
Okay lady, you’re the one paying me.
74. The Invisible Man
I’m a lawyer who investigates the backgrounds of witnesses for our cases. I found someone who was pretending to be someone else who died as a kid. My boss alerted the feds and they investigated and found out he had faked his demise 20 years before to avoid an embezzlement trial. He got convicted for the false identity because he filed taxes in the fake name.
Not sure about the original embezzlement charge.
75. It’s Not What It Looks Like!
So there I was, trailing a woman that a guy thought was cheating on him with an old boyfriend. It led me to a hotel where I got some pretty steamy video footage. When I went back to the guy’s house to drop off the invoice, I overheard him fighting with the girl. Something about her meeting up with the guy for some kisses, and that was all.
76. Money Talks
One of the funniest things about this business is how many angry clients like this just come barging in and making ridiculous demands. They all seem to think they’re in a movie or something. Sometimes, they’ll even scream things out like, “cost is no object,” right up until we tell them that we charged $100 per hour. Then cost suddenly becomes an object…
77. Not What We Do
I was asked by a prospective client to kidnap a child whose parents were in the middle of an ugly custody battle. One of the parents was keeping the child in violation of a court order, and this family member thought that coming to me and making this request would be the easiest solution. Nope. I’m afraid I had to take a firm pass on that one…
78. Small World
My grandfather was a private investigator. He was once asked to tail a well-known delivery truck around its route leaving Central Scotland, traveling south, and then back again. He took up the case and followed the truck, but he was shocked at what he found. It turned out that my other grandfather was the one driving the truck! They never did speak to one another from what I can remember.
79. Fair-Weather Friends
The most fun I ever had on a case was busting a workers’ comp cheat. The guy made my car since I was there a lot over a long time, so I used another car. Then it turned out the neighbor of the subject I was working on just let me use his carport. He’d hang out with me, we’d sit and shoot the breeze. P.I. work is mind-numbingly boring sometimes, but he’d provide drinks as we hid behind the woodpile or a car.
I hated it when that job ended.
80. Doing Him A Solid
I once had a guy admit to setting his house on fire just because I was nice to him. I mean, it was super obvious and he knew I’d figured it out, but I just talked to him about football and all that, and right before I left he just flat out admitted to it. If all my jobs were as easy as that guy, I think I’d probably be a very rich man.
81. All In Two Days’ Work
I hired a P.I. to hunt down a customer who stiffed me for over $10k in airplane repairs. P.I. found him in two days. The guy had bought a house under his deceased brother’s name and started up a courier business using his airplane. I already had a mechanic’s lien on his other aircraft, and in order to keep his business and license with the FAA, he was forced to pay me back.
The P.I. ended up comping the job because he found the guy so quickly that he felt bad about charging me.
82. Fool Me Once
We had a babysitter who we were pretty sure had been ripping us off. So, after we parted ways, we had our neighbor who was a P.I. do a background check. Turns out, every time things went missing, the babysitter had either a court appearance or another fine for their multiple offenses. Note to self, run the background check FIRST.
83. Whatever Floats Your Boat
There are some strange tastes out there. There was a couple that would hire me once a year to catch the wife getting intimate at a sleazy motel with the curtains open. The guy tried to play it off like he was actually trying to catch her. “I found a motel key that said room 109. I leave for work at 8 AM and my neighbor says she usually leaves at 9 AM every Tuesday, etc.”
If a dude wants to pay us a grand to take photos of his wife, I’ll play the cameraman. It’s easy money, and the risk that an altercation happens is almost nothing.
84. Mowing Down His Case
This was the funniest case I’ve ever heard of by far, in my opinion. My brother-in-law is a private eye. One time, he was hired to follow around a worker comp victim with an allegedly bad back. He filmed the victim lifting a lawnmower into a truck bed. A riding lawnmower. With his bare hands. And with no struggle whatsoever. How ridiculous is that!
I once got hired to follow another private investigator who, it turns out, was also hired to follow me. I’m still not quite sure what that was all about…
86. Horse Power
I’m a private investigator. I once had to work a case involving a missing horse. While I was investigating, I ended up almost getting shot by a bunch of angry rednecks. Due to reasons beyond my control, I’m not sure if I can mention any more specific details about that case. But suffice it to say that I spent a lot of time that evening thinking about what I was doing with my life…
87. Tie-Me-Up Elmo
I once found a hogtied Elmo covered in white paint in the basement of a vacant building in a terrible part of town.
88. When The Hunter Becomes The Hunted
Oh man. I’m a P.I., and one time this guy made me as I was following him and started chasing me. It was actually good evidence because I just started videoing the speed and maneuvers we were doing as he chased me—he had his young boy with him in the car and it was a custody case. Lost him with the ol’ run a red light at a busy intersection.
Dude was not a good dad, from what I observed.
89. Retracing Her Steps
A private investigator came into the bar I was bartending at years ago, and showed me two pictures. One was of a girl in her early 20s whose family was trying to track her down, and one of a guy in his late 20s that they suspected she had run away with. The guy in the picture had a charge on his debit card from my bar from a week earlier, so the investigator came in hoping that I would remember if the girl was with him that night.
I did not recognize the girl at all, but I remembered the guy. He had come in with two other guys around his age. They all got pretty intoxicated, but all they really did was shoot pool. They didn’t cause any problems and they actually tipped me really well. I never heard anything else about the girl, so I don’t know if the family eventually found her or if she disappeared for good.
I just now remembered that her first name was Katie. I can’t remember the guy’s name though.
90. A Case Buffet
I am a private investigator and I have come across many cases. Once, a police department in a small town in the Appalachian Mountains wanted me to keep an eye on an old lady. Another time, a manager at a Walmart in Indiana wanted me to watch a couple of employees because he thought they were talking about him behind his back.
A tenant of an apartment building hired me to watch his landlord, who also hired me to watch the tenant. A retirement home hired me to watch one of their tenants: The tenant was a 90-year-old lady with epilepsy, but the pay was great. The weirdest one of all? A “Make America Great Again” supporter hired me to watch his neighbor.
Why? Because he was convinced his neighbor was “a Soviet.”
91. Gotta Keep Your Energy Up
I’ve been a P.I. for about 3 years—mostly for disability scams, no cheating wives or anything. The coolest-slash-strangest thing I observed was this low-level criminal. He was supposed to be disabled, but he would spend all day going from Walmart to Walmart. In each Walmart, he would fill the shopping cart full to the brim with energy drinks.
Then he’d walk briskly out the door without paying, throw them in his trunk, and take off like a bat in the night. At the end of the day, he sold a trunk-load of energy drinks to a corner store and I videotaped him walking out with a wad of cash. That’s actually how I got him. Not quite the way I think he was intending to go out.
92. The Year Of The Scammer
I deal with a lot of cases where older people get a phone call from the “IRS” and get tens of thousands of dollars on prepaid credit cards and read the numbers off the back to the guy on the phone with the Indian accent to pay their tax debt. This happens a lot actually. It’s just weird that otherwise intelligent people can be talked into doing stuff this dumb.
Please talk to your grandparents. Make sure they know this is a common scam and there are many, many variants of this scam. No reputable business or organization takes payments by iTunes gift cards. Their grandchild did not get locked up in Mexico, they aren’t overdue on their electric bill and their power is about to be shut off.
The authorities don’t have an old warrant that they’ll dismiss for a small fee. A lot of these victims are so sold on the lie that store clerks will stop them in the middle of purchasing $3,000 in cards, TELL them that they are being scammed, and these victims will argue with them that they need to pay the guy on the phone.
93. It’s Like I Don’t Even Know You
I found out that the man I’d been involved with for six months had not one, not two, but three aliases.
94. Clean Them Out, Girls
That our cleaning ladies got involved with a smuggling ring and set us up for a robbery that totally emptied our house out.
95. Prove Me Wrong
Some idiot in Nowhere, Kentucky reported a daycare center that they thought was a secret organization. We all thought they were stupid or crazy for doing it. Turns out, there really was a secret organization in the basement.
96. Don’t Look Under The Bed
My half brother said that he was a private investigator until he found a whole bunch of intimate toys under a murder victim’s bed.
97. Done And Dusted
Not me personally, but I worked with a guy whose subject kicked the bucket on the first day of surveillance. I’m sure the final report must have been legendary. “The claimant died.”
98. The Worst Human On The Planet
One girl offered to watch her roommate’s dog for the weekend, then got annoyed by its barking so set it on fire. She is the only truly evil person I’ve ever seen.
99. All The Better To See You With, My Dear
A woman I know had to get a private investigator as part of her divorce. The husband had been cheating, but in order to get infidelity as part of the divorce hearing, there needed to be a witness who saw him go to the other woman’s house after 10 pm and stay there for at least an hour. It was a slam dunk, probably because the P.I. was so unassuming.
She was like a 50-year-old woman, who you never would’ve guessed was a P.I.
100. On The Wrong Side Of History
Girl ran away from home. She had been getting bullied at school. It turns out her grandfather was a guard at Treblinka.
101. The Wedding Photographer
I represented the husband in a divorce. On the day of the trial, opposing counsel presented shocking evidence. The wife’s attorneys produced photographs from a private investigator that they claimed proved adultery. The photos were of my client, the husband, wearing lingerie and a long brown wig, engaging in act of intimacy with another man. I was able to successfully exclude this from evidence…because the wife was the photographer.
102. A Little Dusty
I had a woman with an expensive fur coat who claimed that the laundromat ruined it. It was a bit ruined, but the laundromat said that the stains were already there. The judge ordered an expert opinion from a private investigator—and he revealed so much more than we bargained for. The coat had traces of drugs all over it. They raided her place where they found her husband’s big stash of drugs. She should have just taken the stains.