Private Investigators List Out Their Most Bizarre Cases

Investigating cats and people who pretend to be blind— all in a day’s work


Private investigators are usually hired to follow cheating spouses and to do the occasional background check on employee. It’s not the most interesting job in the world. But, sometimes they get a really funny, awkward case that is unforgettable. Private investigators of Reddit list out the most bizarre cases they have been assigned to.

1. Suspicion Confirmed

A couple was divorcing and the wife was sure her husband was sticking random items of hers up his a**. He was. [you_are_d00med]

2. Detective T*ts

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 Ti*s” which, most regrettably, stuck and spread to all of the other lawyers I dealt with. [VenBede]

3. Legally Blind

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. [trackerjakker]

4. Ace Ventura

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. [questionguy1000]

5. The Sick Husband

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 Cams 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. [AvoidableBoat67]

6. Meta

I got hired to follow another investigator who, turns out, was hired to follow me. [Zero_kys]

7. The Cheating Pet

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.[TheGenesect]

8. The Scary Cult

I’m a private fire investigator. I’ve seen some people do some weird sh*t but one of the strangest was the guy who was convinced that the church next door set his house on fire.

He told us about how they came over and prayed on his car that it would break down, then it did. Then they came over and prayed that his house would burn down, and it did.

Turns out the “church” next door is kind of a cult. And by kind of, I mean really a cult.

But they didn’t burn the house. The tenant’s crazy ex boyfriend did. Thought I was going to get to interview cult members for awhile though. [fireinvestigator113]

9. The Lazy Teenager

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. 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.

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. [CyberTractor]

10. The Porn Investigator

Former PI here. A hedge fund manager hired us to look into him (he was investigating himself) to see what kind of information is out there that could be used to hold him or his family ransom. This same guy had previously hired my firm to go through porn sites after his girlfriend’s ex-boyfriend claimed she was a porn star. [smellbound]