Unspeakable Times

Private Investigators Describe The Most Bizarre Things They've Seen On The Job 

Lowe Saddler
Updated February 28, 2020 213.8k views 15 items

Private investigators don't just exist in movies and books. The occupation is a legitimate one, and almost as sordid as fictional detectives make it appear in true crime shows. Reddit investigators might not encounter as many bizarre cases as Sherlock Holmes or Jessica Jones, but their tales can still be pretty sensational. 

Real PI work requires intense preparation and lots of training; you can't solve a mystery without a certain skill set. It's impossible to plan for everything private investigators see, though. Most of these professionals treat their work with respect, but they're still shocked when cases go off the rails. A detective's day is full of surprises. 

A Husband Inserted His Wife's Personal Items In A Very Personal Place

From Redditor /u/you_are_d00med:

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

He was...

Man I wish I could post video. What you don't realize is I didn't set up cameras in the bathrooms so you gotta picture this dude walking around the house with this toothbrush sticking out of his [rear end]. Because of course he is naked, I would assume the clothing pushing on it would make it more uncomfortable than it already was. And dude had a semi. I am still scarred from these images. I could never tell if it was bristles out or in tho.

A Nurse Pretended To Be Disabled So She Could Strip

From Redditor /u/VenBede

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...

A Crazy Ex Was Mistaken For A Crazy Cult Member

From Redditor /u/fireinvestigator11

Late to the party but 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.

A Hedge Fund Manager Wanted To Investigate Himself

From Redditor /u/smellbound

Former PI here. Most cases I worked on were for large litigation firms and finance institutions (fraud, embezzlement, insider trading, etc). But we would get the occasional eccentric millionaire with strange requests... Another 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 [adult] sites after his girlfriend's ex-boyfriend claimed she was [an adult film] star.