Private Eyes Reveal Their Most Ridiculous Cases


The Lucky Wanderer

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.

The next story is about a P.I. who had to do a little digging to find someone completely unknown.

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Unknown Father

I hired a private investigator to see if the 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.

The next story is about dealing with a case of mistaken identity.

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Mistake Identity

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.

The next one is a strange story about a couple who had no family.

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The Couple Who Never Existed

I’m an attorney and occasionally need to hire a P.I. to track someone down. We had a case where a 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.

My office was retained to see if the family would pay it off. I did my normal search and couldn’t find any next of kin. I spoke to the neighbors, who were friends with the couple for 20 years, but the neighbors knew nothing.

I reached out to our P.I., who asked for a week to get a report for me. Finally, the P.I. calls to say there’s no report and he’ll give a discount on the bill. There is no record of the couple, they simply appeared in the 80s.

In fact, the couple’s 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.”

The next story is about a P.I. who was unwittingly dragged into something more sinister.

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Guilt Ridden

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 something. 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.

I thought it was weird at the time, but I wasn’t going to reject $2,000. He kept asking me, “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 watching the news. What I saw next chilled me to my bones. The guy I’d been watching had been killed. 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.

The next story was so bad, the FBI had to get involved.

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An Unexpected Find

My brother was a private investigator in the early 1990s. He worked for a law firm. I was in my early 20s, and he got me a gig as a process server. 

He was working on 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 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 and getting a briefcase with financial information in it. 

We went and waited down the road until everyone left, then we went in and got the briefcase. We take it back to the attorney’s office and he calls the lady to give him the combination. He opens it up and freaks out. 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. My assumption is that the guy had been plotting some kind of serious attack on a plane. 

The young woman in the next story just could not give up on a cheating spouse.

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Caught Out

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 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. 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. 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. I hope she took him for all he was worth.

The next story is about a coach doing way more than he should’ve been doing.

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More Than Coaching

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, and the story broke with all the evidence I had collected. I was not named in the story as I had requested not to be.

The woman in the next story got caught out in an outrageous lie.

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Insurance Fraud

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.

The P.I. in the next story gathered evidence of a man who should be jailed for life.


Not What They Had Expected

I’ve been a private investigator for 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.

The next P.I. caught a woman who thought she could get away with scamming insurance companies.

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Things Are Not What They Seem

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 on 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?’”

The next story is about a nurse who was making some extra cash on the side.

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Suspicious Nightlife

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 videos. 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 that 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.

The guy in the next story was convinced his phone was wiretapped.


Stop Bugging Me

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. No devices were implanted in his phones. 

We’re getting ready to leave and he says: “Look, I’m not crazy. Pick up the phone, press 9 and you’ll start hearing all sorts of 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 advised him to install a private phone line. We ended up billing him like two grand for that visit.

The young P.I. in the next story would learn that it was not an easy job to do.

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Not For The Faint Of Heart

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.

The company in the next story would make a big mistake by replacing their best worker.

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Not Suitable For The Job

When I was an investigator, I was asked 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 and 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. 

Didn’t 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.

The P.I. in the next story would find out that his client was not as innocent as he had claimed.

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Candid Camera

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 up some of the incidents. 

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.

The next story is about a P.I. who got an interesting case to do and got unexpectedly caught.

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Breaking And Entering

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.

The guy in the next story heard everything about his friend’s legendary great-uncle.

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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.

The woman in the next story would not leave this married man alone.

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Stalker Alert

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.

The guy in the next story had a story so unbelievable that the P.I. was laughing all the way to the bank.

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Monitoring The Neighbor

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 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. 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. I learned that normal P.I.s never take these so-called “domestic” cases because they are always a huge mess.

The 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. Watch the video the next day—it’s the wind.

The client freaks out and 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.

It turns out lots of people call P.I.s to investigate the TV controlling them, alien abduction, etc.

Lesson learned!

The cheating man in the next story went a bit too far to get back at his ex-wife.

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The Watcher

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 all 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.

The P.I. in the next story got a little frustrated doing a case.

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All In A Day’s Work

We had to follow this cheating husband to the beach in Florida. I got paid to go hang out in a nice beach town. 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 beats 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, 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.

The woman in the next story wasn’t paid enough for what she saw on the job.

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The Things You See

My wife was a P.I. Not a lot of research, mostly documenting insurance scams. In 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.

The guy in the next story almost got featured on a TV special about a case.

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A TV Special

My family member is a P.I. He was working on a case a few years back. Hired to catch a spouse cheating. 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.

Kind of funny, but I didn’t realize it was made into a kind of TV special 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. 

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.

The P.I. in the next story handled a very sad case that he wishes he could forget.

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A Sad End

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.

The woman in the next story found out a little too much about her husband’s affair.

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Too Close For Comfort

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 by her uncle instead. The husband hadn’t met him before. He was cheating on his wife with her father! Absolutely wild.

The P.I. in the next story uncovered a whole family involved in every lie possible.

The Family Tree Of Lies

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 and 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, which turned out to be a rampant cheater for sure, divorce followed shortly. 

To this day, he’s considered an unperson in my family, and no one will tell me what his name was or what team he played for.

The next story is about a P.I. who ran a background check on a guy and found shocking evidence against him.

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Background Check

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…

The P.I. in the next story couldn’t help but get personally involved in a case. 

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Mr. Nice Guy

As a college student, I worked for a private investigation 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 toward this guy.

The woman in the next story had a stinky problem on her hands.

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Stinky Disposal

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.

Disclaimer: In order to protect the privacy of those depicted, some names, locations, and identifying characteristics have been changed and are products of the author’s imagination. Any resemblances to actual events or places or persons, living or dead, are entirely coincidental.

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