Get Premium
Dark mode theme is available exclusively for premium users. Learn more about the benefits of subscribing.
No fees, cancel anytime.
Dark Mode 
No fees, cancel anytime 
19submissions
Finished
19 Strange Things People Discovered When They Hired A Private Investigator
Article created by: Mantas Kačerauskas
I’ve never had any interest in being in law enforcement, but after watching about a hundred true crime documentaries, I have gained an immense appreciation for those who devote their lives to solving cases. And if you’re as curious about the mysterious lives of detectives and private investigators as I am, you’ve come to the right place, pandas. One Reddit user invited PIs and detectives to recall some of their strangest cases, so we’ve gathered their most fascinating stories below. Enjoy scrolling through these tales that sound like they could be plots of television shows, and keep reading to find a conversation with full-time private investigator Tony Smith!
This post may include affiliate links.
#1
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.
RELATED:
#2
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....
#4
I was asked by a lady to investigate her husband because he might be cheating on her. He used to come back late at night with smell of woman's perfume. Turns out he was taking dancing classes and he didn't tell his wife
#5
Client wanted to know why her dog was getting fat. Turns out the dog was getting fed by almost every stranger it encountered while wandering around outside during the day.
#6
I've been a P.I. for about 3 years - mostly for disability fraud, no cheating wives or anything. Coolest/strangest thing I observed was a low level criminal (who was supposed to be disabled), who would spend all day going from Walmart to Walmart.
In each Walmart, he would fill the shopping cart full to the brim with energy drinks (Monster I think), walk briskly out the door without paying, throw them in his trunk, and take off like a bat out of hell.
At the end of the day he sold a trunk-load of energy drinks to a corner store and I video taped him walking out with a wad of cash.
Definitely not as exciting as the movies, but it was a fun day for me.
#7
Cases where older people get a phone call from the "IRS" and get tens of thousands of dollars on prepaid credit cards and read the numbers off the back to the guy on the phone with the Indian accent to pay their tax debt.
This happens a lot actually. It's just weird that otherwise intelligent people can be talked into doing stuff this dumb.
Please talk to your grandparents. Make sure they know this is a common scam and their are many, many variants of this scam. No reputable business or organization takes payments by I-tunes gift cards. Their grandchild did not get locked up in Mexico, they aren't overdue on their electric bill and their power is about to be shut off, the police don't have an old warrant that they'll dismiss for a small fee.
A lot of these victims are so sold on the lie, that store clerks will stop them in the middle of purchasing $3k in moneypak cards, TELL them that they are being scammed, and these victims will argue with them that they need to pay the guy on the phone.
#8
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.
#9
Doing a standard pre-employment background check on a guy, found that he was found guilty in a sexual harassment case. Didn't have the case details at that point and the guy denied it was him. 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 it was him, but claimed it wasn't as bad as it seemed. Pulled the court transcripts. Turns out he flashed a 12-year-old on the beach and said "ever seen one of these before?" He did not get the job.
#10
My uncle is a PI. He got tasked with investigating a collision at an intersection. He found a nearby business that happened to have a camera facing the road which would have collected the footage and got said footage of the collision. The client was definitely in the wrong and caused the accident, then the client was seen abusing 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 which legitimizes his word, however he rolled snake eyes and ended up incriminating himself.
#11
Funniest to me, my brother in law is a private eye following around a worker comp victim with a bad back. He films the victim lifting a lawnmower into a truck bed. A riding lawnmower.
#12
P.I. for 5 year, I had a few exciting, not necessarily strange cases. One incident was of a coach who was sleeping with one of the female players. One of the players that was benched hired me to document the coach for sleeping with one of the starters on the team...They were careful with how they arranged their meetings, and took me a bit to document it, but ultimately got the information. Fast forward a week later and the papers reporting the coach has resigned to work in the family business...fast forward another week later, the story broke with all the evidence I had collected (I was not named in the story as I had requested not to be.)
Another case was my quickest (2 hours). Picked up surveillance after the subject had dinner with his wife at Applebee's, followed to a hospital parking garage and he went in to visit his mother. I stayed to monitor the vehicle, and another shows up. The subject exited the hospital and jumped in the other vehicle...I then recorded him getting a bj. Case opened and closed in 2 hours (paid $1,000 retainer, was able to keep all $1,000 since retainers are non refundable I charged $60/hr and would've only made $120)....I have many many more stories....some funny, some really sad (I specialized in father's rights cases).
#13
Not a P.I but thought this may qualify. My grandfather (P.I) was asked to tail a well known beer delivery truck around its route leaving Central Scotland, traveling south then back again. Turns out my other grandfather was driving the truck! They never did speak from what I can remember
#14
I have a friend who is a PI. She is a former cop, retired. Says it is really boring; lots of sitting around on surveillance or digging for paperwork, working long crappy hours. Never carries a gun. Says being a woman is an advantage as people are more suspicious of a male.
#15
My RA my sophomore year of college was a part time PI and bragged about it to the coed underclassman. Few weeks before spring break he's seen with bruising and black eyes. Some guy he had been following to catch in an affair got a hold of him and beat him senseless.
#16
My mom hired a private investigator on my dad way back when she was pregnant for me she felt like something was wrong cause he said "he just needed time away" In the end he was cheating and my mom left him.
#17
One time I was hired by this really famous author to test the security system in his Hawaii vacation home. His British caretaker set his two dogs on me and I had to escape by hot wiring his Ferrari.
#18
A college of mine was a PI.
He said 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 serve people, including disguises, high pressure tactics and weird social engineering.
He's out of it now because he'd had too many close calls. Serving divorce papers or notices of being sued where you have no idea of the state of mind of the person you're serving to could get interesting to say the least.
#19
Cattle mutilations in the late 70's.
Related on Bored Panda
