10 Private Investigators Shared Their Creepiest And Most Bizarre Jobs –


Since private investigators are hired for the sole purpose of uncovering people’s dirt, it’s hardly a surprise that they carry a few war stories with them. What starts out as a simple infidelity investigation can quickly escalate into a full-blown movie plot.



Since private investigators are truly a wellspring of bizarre, creepy, traumatizing and fascinating stories, I was hardly surprised when I found myself lost in a Reddit thread full of PI stories. I truly believe Hollywood could scrap at least five of their superhero remakes and replace them with these compelling PI stories. Humans are truly duplicitous and weird.

So, without further adieu, I humbly present to you 10 truly bizarre stories from private investigators on the job.



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

He was.

Did surveillance on a nurse. She was supposedly so disabled that she couldn’t work. They suspected she was working. Easiest surveillance I ever did. I arrived. She got in her car 10 minutes later. Followed her, with no complication, to a strip club where she went in and began doing her thing.

Club had a posted prohibition on video. So I had to go in and watch her dance so that I could testify that I saw her dancing when it went to court. Over the next few days I followed her to three other strip clubs and did the same.

That month I turned in the sketchiest expense report of my life.

Eventually it went before the WC Board. When the judge asked why she was stripping she just shrugged and said she made twice as much money than when she was nursing.

Benefits got yanked. Insurance company was happy. But the company lawyer gave me the nickname “Detective Tits” which, most regrettably, stuck and spread to all of the other lawyers I dealt with.

Worse night of my life, man.

Was hired to follow a woman who claimed she was completely blind (collecting insurance money of course). Spent the day following her around as she DROVE from store to store in a church van.

Someone wanted to know what their cat was up to when they were working. Paid me to tail it. I don’t like wasting my time but the works not always busy as a PI. Turns out the cat just walks around the streets, licks itself and climbs trees….

Not a PI here, but someone who was confronted by one and told it was the weirdest thing he’s had to do.

A roommate I had in college was a strange guy. This guy came from the other side of the country (I’m US). He went out at all hours of the night, never showed up for class, slept during the day, and drank more energy drinks than is healthy. His parents were worried about him, apparently, and hired a PI to trail him.

Now, living in a college dorm in a part of campus where only freshman live makes an adult who isn’t janitorial staff stick out like a sore thumb. So, I picked up fairly quickly that this guy was hanging around the dorms. Thought he was just cruising for some freshman, and didn’t bother him.

A few weeks later, I was walking back from the dining hall, and he approached me (it was a public place) asking if we could talk somewhere private. I was weirded out and told him we could talk right here.

He told me he was a PI hired by my roommates parents to trail him because his parents were concerned, and he wanted to ask me about my roommate’s dorm habits. We then left to the coffee shop to talk about my roommate.

My roommate apparently liked to go walk on the beach at night for stupid amounts of time, hang out at Steak and Shake playing game on his phone and Nintendo DS for hours on end, and cruise thrift shops for some reason. I told the guy that the dude just slept and didn’t even have any personal affects in the room besides his clothes.

The PI and I both realized that this kid pretty much had no direction or motivation in life, and his parents usually pushed him to do everything. He said that this kid’s behavior was the most bizarre pattern of activity he’s pretty much seen.

To explain the kid’s actions, college was the first alone time he’s ever had, and he was savoring it doing whatever he wanted. I ended up feeling for the guy and reached out to him. He changed majors from engineering to a psychology degree because he wanted to learn how the mind worked, and he suddenly became super-interested in college. Ended up being a cool guy once he realized he was not in his parent’s grasp anymore.

Worked as a PI for about a year once when I was much younger. This wasn’t a case I took, which will be obvious by the end why I didn’t.

We had an office on the ground floor of a building near the county courthouse, with a door that opened to the street. This meant we actually got a fair amount of foot traffic. If I had nothing going, I closed the office round 5pm. Around 4:45pm a lady comes in asking all the usual questions. “Are you REALLY a PI?” “What cases do you take?” “How much do you charge?” Yada Yada Yada, I spend 10 minutes going through all that. This lady seem pretty wound up, which is not unusual, people don’t come in looking for a PI when everything is great. Often it’s because they are having one of the worst experiences of their lives and are desperate for help and haven’t gotten it elsewhere.

I ask her to tell me what brought her in today and be as detailed as possible. She tells me that someone stole her ideas and now she’s being followed. I’m thinking, great, potential intellectual property case. I ask her to start from the beginning, what were these ideas? She starts telling me about here last gynecological exam. I immediately stop her and ask her what this has to do with her ideas being stolen. She flips out.

She begins screaming about how the doctor implanted a listening device inside her and that’s how they are stealing her ideas. I do my best not to react. She screams, “You don’t believe me either! But I have proof!” She runs out of the office and comes back a minute later with a large envelope. She pulls out x-rays of her pelvic region and shoves them in my face. “See! Right there, that white spot on my ovary, that’s the listening device!” I agree that there is a small white dot, but tell her I’m not a doctor or an expert in listening devices and can’t confirm that it is one. In reality, it didn’t look like anything to me, I know it wasn’t an electronic device of any kind, let allow one that can capture you ideas and transmit them to vans that were following you around now.

She goes on to tell me how the doctor was in on it and they were stealing her ideas and making them into TV shows for Telemundo. This is the part where I tell you this middle aged, blonde haired, blue eyed lady didn’t speak a word of spanish.

I ask her about the vans that were following her. They were different colors and often different drivers. But they were definitely following her around and that’s how they were collecting her ideas. I’m looking for a polite way to tell this lady I won’t be taking her case, but she won’t let up and insists I do something about it. I finally catch a break. I tell her the retainer amount I would need to get started. She responds, “Well I don’t have that kind of money. When we win in court you can have half the settlement.”

In the state I live in, only lawyers can work on contingency. Meaning their payment is contingent on them winning the case. PIs and all people that might work for these lawyers still have to be paid no matter what. I tell the lady this. I thought she was about to explode. I tell her I can’t break the law, but if she were to find a lawyer willing to take up her case, I could work for that lawyer as their PI.

She calms down and says thanks for hearing her out. I say no problem. I ask her if there was a family member she could call or a doctor she did trust that she could see. She tells me she’s not crazy and storms out. I felt horrible for her, she was obviously living in terror and needed professional help. This was the first time I encountered the seriously mentally ill. In retrospect, I should have called the police and tried to have them intervene, I regret that. I can look back now and cut myself some slack for being young, and caught alone and off guard, but I still wish I would have done more. At the time I just wanted to get her to leave peacefully.

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

I’ve worked a few bizarre cases, including one involving a stolen horse and almost getting shot by rednecks. But due to legal reasons, not sure if I can mention that one.

There was a workers compensation case I worked last year. I was told to get film of this older lady who had supposedly be on total disability due to a severe ankle injury. Seems cut in dry. But she lived in a motel in the middle of nowhere Pennsylvania. The motel was called “Johnnies” I looked up the place online, and found reviews of it on google. There were really shitty reviews including one that said the place was mostly run by the owner’s son, who was a druggie and would ask people who stayed there if he could buy any prescription drugs they had. That isn’t sketchy at all.

So I show up to this ‘motel’ which looked like it hasn’t been renovated in 40 years. It was a small motel, 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. 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 it was a sign that said “office” and instructions for long term customers of the hotel on where to drop their payment. There was a door bell. 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 1 desk. Nothing else. There was shag carpeting and really dark colored walls and a lava lamp on the desk. I realize that this was the owner’s son, Johnny Jr. I give him some fake story how I’m an insurance adjust 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 repped by an attorney and likely knew a PI might be looking for her. I tell him, no, I just needed to confirm she lived her and bolted.

Now, park in the parking lot with view of the room Johnny Jr pointed at. A couple hours go by and then some old guy is standing near my car getting stuff out of his car. Johnny Jr walks out and starts talking to him. I realize the older guy is Johnny Sr. 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 the “insurance adjuster” who visited earlier. Johnny Sr having seen some shit in his day immediately says “that wasn’t an insurance adjust you idiot, that was a PI, insurance adjusters don’t work on Sunday” He tells Johnny Jr to tell Mary to watch out that a PI might be in the parking lot.

My car is tinted. I think I’ll be fine. Except, the parking lot I’m in is shared with a Diner. The owner of the diner comes out and starts talking to Johnny Sr. Apparently I parked in front of a shed that the cleaning staff for the motel use. Johnny Sr now starts talking to the owner of the diner 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 and she leaves. Johnny Sr then goes into on of the motel rooms, where apparently he lives. He constantly stands in the door way looking at my car. I leave as soon as he looks the other way.

I would come back later in the day and would get film of the lady I was supposed to watch. Was totally faking her injury. Johnny Jr and his girlfriend actually came out a couple times and tried figuring out what cars might be a PI’s car. But because they saw my car earlier that day, they didn’t seem to suspect it as suspicious.

I’m a PI (among other things.)

I haven’t had any bizarre tasks, though I have had some interesting situations, and I’ve performed surveillance on cheating spouses as well as factual worker’s compensation and public liability matters.

One matter which really made an impression on me was where a person had a fatal vehicle incident and a claim was made that it was a workplace injury. I don’t know what on earth happened with this claim but it was five years before the insurer gave it to me.

There were some questions about it – the person making the claim alleged to be the worker’s wife, though work colleagues did not know her, and also the incident was almost 200km from the workplace.

When I spoke to former colleagues a lot of them struggled to remember him. This really was so sad. It left a deep impression on me that what are we once we are dead if we are not even memories.

I did, however, learn he stayed at a caravan park during the working week. I called that place but the owner said it had changed hands and he didn’t know the guy, he didn’t have any old records, and he didn’t know where the former owner was. He did remember the former owner’s name however.

I called everyone in the phone book for the state with that name. I finally got my man, and he remembered the deceased vividly … along with his wife and son. It was tremendous! I learned the guy would stay near the workplace during the week and travel back home, to a remote town, for weekends.

I drove all the way to that town but couldn’t find the wife. She wasn’t at any address I had, nor did she answer her phone. I got petrol and asked at the counter if they knew the family, and they said it might be so-and-so and directed me to a house. I went there, turned out to be the wife’s parents, they called the daughter, she arrived and both mother and daughter had a big cry while showing me all their photographs of the guy. It was very moving, and I was so relieved to have real evidence the guy ever actually existed after how his co-workers were finding it hard to remember him.

The story was very sad; he died on the way to work on a Monday morning. Normally he would travel to the caravan on a Friday night but this particular weekend was mother’s day. He stayed Sunday night and travelled Monday, early in the morning, ran off the road and passed away 🙁

I was able to determine the lady was genuinely his wife, that he was on his way to the workplace, that it was his regular route to work, and so on. I supplied this to the insurer. I never – well, rarely ever – hear what happens to a matter so I only hope it was finally settled.

FINALLY! A question I can answer! Been a P.I. For a going on a year now and the strangest case I had was of a woman asking us to find out if her husband was cheating on her. She said there was something off in the house as if feeling something and she wanted to know what it was. So she suspected her husband of cheating.

So I show up and install Nanny Cam’s in her house for the weekend upon her approval and where to place them. She works all weekend and this was the best route. Well 3 days go by and I collect the footage and come to find out the husband was “touching” his 8 year old step daughter. After seeing that I rushed to the court house with a copy of the footage and got a court order for the police to go and get him.

Any PIs ever get 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?

Yes, constantly.


All right, here goes. After I got out of the Navy, I worked for one of the top PI firms in Houston. Because of my electronics background, I’d usually go along on the jobs where were were checking for bugs and hidden surveillance devices.

We got a call from a client who was sure that his office was bugged because his client knew everything that he was doing before he did it. His office was a mobile trailer that was on his client’s site. He was a subcontractor for a big oilfield construction company.

We did a full electronic sweep and found nothing (this was back in the early nineties, didn’t have to worry about burst transmissions, etc.) No devices implanted in his phones. He insisted on a full physical sweep of the trailer, inside and out. So we crawled under the trailer and got a ladder and inspected the roof. Still nothing.

We’re getting ready to leave and he says: “Look, I’m not crazy. Pick up the phone, press 9 to get an outside line, and you’ll start hearing all sorts or clicky sounds.” Turns our his office phones were routed through the corporate PBX of his client. They didn’t have to bug his office, they could just “pick up an extension” inside the main building and listen in to whatever they wanted. We weren’t even sure if it was illegal. We advised him to install a private phone line that he paid for if he wanted private conversations. We ended up billing him like two grand for that visit.

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