Private Investigators Reveal The Craziest Things They’ve Seen On The Job

11 min

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:

14.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….

13. 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.

12. …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.

11. “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.

10. Ew

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

He was.

9. “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.

8. 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.