September 18, 2023 | Mathew Burke

Private Investigators Recall Their Most Unforgettable Cases


In movies, books, and TV shows, there are hardly any jobs that seem cooler than detective. From hunting down bad guys to uncovering earth-shattering secrets, it's never a dull moment with these sleuths. But what is it like to actually have that job in real life? Are the cases that real people bring in ever as exciting as the ones that we all picture in our imaginations? Well, in at least some cases, the answer to that is a resounding yes! Here are 50 stories of some of the most memorable experiences that real-life private investigators have ever encountered on the job.


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!

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2. 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!

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3. 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.

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4. 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.

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5. 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?'"

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6. 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.

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7. 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.

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8. 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 peeler 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 clubs of the same caliber 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 Chests" which, most regrettably, stuck and spread to all of the other lawyers I dealt with.

Worst night of my life, man.

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9. 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.

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10. 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.

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11. 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.

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12. 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.

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13. 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.

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14. 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.

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15. 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.

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16. 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.

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17. 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.

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18. 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…

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19. 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.

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20. 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.

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21. 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.

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22. 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!

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23. 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!

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24. 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.

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25. 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.

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26. 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.

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27. 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.

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28. 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…

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29. 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.

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30. 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 undocumented 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.

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31. 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.

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32. 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.

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33. Framed By Frame

I was once hired by this 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.

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34. 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.

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35. 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…

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36. 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.

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37. 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.

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38. 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…

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39. 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.

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40. 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.

Fun stuff!

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41. 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…

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42. Not What We Do

I was asked by a prospective client to abduct a child whose parents were in the middle of an ugly custody battle. One of the parents was keeping the child in breach 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...

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43. 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.

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44. 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!

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45. Inception

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…

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46. 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…

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47. 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.

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48. 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.

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49. 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.

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Sources:  Reddit,




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