Private Investigators Reveal the Most Bizarre Thing They’ve Had to Do on the Job

I went through a phase when I was younger where I loved to watch old PI movies. There’s something glamorous about the way the profession used to get the Hollywood treatment; it’s danger and sex all wrapped up in the sad, suave face of Humphrey Bogart.

That’s obviously not what it’s really like. Just ask these 14 AskReddit users:

1. Here, kitty kitty…
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 work’s not always busy as a PI. Turns out the cat just walks around the streets, licks itself and climbs trees….

2. Oh, shit!
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.

3. …come on, lady
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.

4. “Over and over and over”
I worked for a PI firm (not as a PI though).

The saddest case we had was a stunning 24-26 year old woman who’s 60ish 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 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 footage of them shagging in the back seat (classy!).

We gave the footage and report to the client who promptly burst into tears and paid the $1800 or so invoice.

The saddest part of the story is she came back 4 times. Each time he was caught literally with his pants down. At the secretary’s house, shagging in the car, shagging 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 we were going to stop taking her work. It was just cruel to keep taking her money to show her footage of her husband banging his secretary over and over and over.

We never saw her again. I hope she took him for all he was worth.

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

He was.

6. “If we are not even memories”
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.

7. What’s in the suitcase??
I have a story about this. My Brother was a PI in the early 90’s. He worked for a law firm. I was in my early 20’s and so he got me a gig as a process server.

He was working a particularly nasty divorce case. Husband was married to an american woman (one of several wives) who was over being in the family and wanted out. Also, she worked for NASA.

He was tasked with going into their house, which was in her name (she wasn’t living there, she was in an apartment until this was settled) and getting a briefcase with financial information in it. Since I was the process server, I had to go along in case someone was home for whatever reason.

We went and waited down the road until everyone left and went in and got the briefcase. No big deal. We take it back to the attorney’s office and he calls the lady and says he has it. She gives him the combination he opens it and it was full of technical plans from Boeing for the Apache helicopter.

Attorney says “Uh oh”, instantly shuts the briefcase, tells me and my brother to leave now, so we did. We never heard any more about that case at all, other than he contacted the FBI over it.

8. Meta
I got hired to follow another investigator who, turns out, was hired to follow me.

9. “Seriously mentally ill”
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.

10. Freedom!
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 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 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.

11. Why was a PI delivering this news?
Not a PI, but I met one. I was at my friend’s house and he got a knock on the door.

“Hello, sir, are you X?”

“Yeah, why?”

“[explains that he’s a PI and that he’d like to talk in private]”

“Nah, I’m fine just talking here at the door.”

“[shows him a picture] Do you know this man? His name is Y.”

“Yeah, that’s my great-uncle, he’s vacationing in the Congo right now, why?”

“I’m sorry sir, but your great-uncle died of hepatitis. [elaborates how his great-uncle, a priest, was with a sex worker and got infected and died]”

I was in the living room eating pizza the whole time, pretending to be watching TV.

12. Corporate Eavesdropping
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.

13. Missing Person
A private investigator came into the bar I was bartending at years ago and showed me two pictures. One of a girl in her early 20’s that her family was trying to find; the other of a guy in his late 20’s that they suspected she had run away with.

The guy in the picture had a charge on his debit card from my bar 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 got pretty drunk 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 guys name though.

14. Jeez, this is terrible
I had a client who hired me to investigate her husband. She claimed he was acting suspiciously and wanted to know why.

I tail him for two weeks and I myself start getting very curious and suspicious. This guy is going all over to different outdoor stores and buying up supplies in cash. Must have been to 10 different stores and bought enough stuff to stay out in the woods for a couple months. I follow him to a spot where I think he is stashing it all.

Long story short I work out that he is in severe financial trouble and he and his wife are about to lose everything. I realize this guy is going to try to fake his own death so his wife can get the insurance money, but she has no clue. I followed him all day every day and wasn’t going to fill her in until I was absolutely sure.

The very last day, I wasn’t able to see, because I couldn’t get too close, but he tried to drive his car off a small cliff over the coast and make it look like he died in the car or the ocean. But, it turns out he jumped out too late and his foot got caught under the seat. The speed of the car kept the door pushed on his leg just enough to drag him over the edge. He went down with the car and died. And the worst part, because he technically killed himself in a fraud attempt, his wife didn’t get any of the insurance money.