And there were so many wild stories!
Here are some of the top responses:
We also included responses from private investigators inthisthread.
“I got hired by a wife to see if her husband was sleeping with his secretary.

In prison, he came into some money and hired us to prove he was innocent.
This criminal genius told us this plan on a recorded phone call from jail.”
The strangest thing I observed was a low-level criminal who would spend all day going from Walmart to Walmart.

Definitely not as exciting as the movies, but it was a fun day for me."
u/straight_edge_PI
4.
She had bought the condo from him originally.

I met her to discuss the case, and she seemed rational.
She agreed to let me install a hidden camera setup with a motion detector.
She was to call me if anything happened to make her think he’d been there."

“A couple of days went by, and she called.
I went by and got the tape (this was before digital recording) and checked it out.
There was nothing on it but her.

He’s a space alien, after all.'
She had not previously mentioned this vital tidbit of information.”
u/DoktorInferno
5.

Anonymous
6.
“This case was my quickest (two hours).
I picked up surveillance after the subject had dinner with his wife at Applebee’s.

I followed him to a hospital parking garage, and he went in to visit his mother.
I stayed to monitor the vehicle, and another showed up.
The subject exited the hospital, jumped in the other vehicle, and got a blowjob.

Case opened and closed in two hours.
u/philds2nuts
7.
I spent the day following her around as she DROVE from store to store in a church van.”

u/trackerjakker
8.
“PI for five years, and I had a few exciting cases.
One incident was of a coach who was sleeping with one of the female players.

A week later, the papers reported the coach had resigned to work in the family business.
Another week later, the story broke with all the evidence I had collected.”
u/you_are_d00med
11. u/bojangles001
13.
This happens a lot, actually.
It’s just weird that otherwise intelligent people can be talked into doing stuff this dumb.
kindly talk to your grandparents.
“No reputable business or organization takes payments by iTunes gift cards.
u/VAofficer
14.
“Some guy assigned me to investigate another private investigator while simultaneously telling that private investigator to investigate me.
u/w8up1
15.
“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 the smell of a woman’s perfume.
Turns out, he was taking dancing classes, and he didn’t tell his wife.”
His office was a mobile trailer that was on his client’s site.
He was a subcontractor for a big oilfield construction company.
He insisted on a full physical sweep of the trailer, inside and out.
So we crawled under the trailer, got a ladder, and inspected the roof.
“We were getting ready to leave, and he said, ‘Look, I’m not crazy.
Turns out his office phones were routed through the corporate PBX of his client.
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, $2,000 for that visit.”
u/dcfix
17.And finally, “I did surveillance on a nurse.
She was supposedly disabled and couldn’t work, but they suspected she was working.
Easiest surveillance I ever did.
I arrived, and she got in her car 10 minutes later.
I followed her to a strip club, where she went in and began doing her thing.
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 Workers’ Compensation Board.
Benefits got yanked, and the insurance company was happy.
Worse night of my life, man.”
u/VenBede
Note: Some responses have been edited for length and/or clarity.