Private Investigators Reveal Their Most Shocking and Crazy Cases

From keeping an eye on their clients' partners to rummaging through piles of documents, hoping to find the proper evidence crucial for winning the case, private investigators witness many strange things as part of their jobs.

Working as a private investigator not only involves following people to find out what they are up to but there are other responsibilities that only a few know about.

Some private investigators opened up about their work experience, sharing some of the most shocking moments with other Redditors. They never thought their job would make them work on such crazy cases.

Comments have been edited for clarity and grammar.

1. They Had to Stop Working for Her

u/AviMin: I worked for a PI firm (not as a PI). The saddest case we had was a stunning woman, around 26, whose 60ish-year-old accountant husband was suspected of sleeping with his secretary.

The client hired us to follow him while 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 inappropriate footage of them 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 four times. Each time, he was caught cheating. At the secretary's house, in the car, in the office with the blinds open in the middle of the day—you name it.

After about $15k worth of invoices, we sat down with her and explained we would stop taking her work. It was just cruel to keep taking her money to show her footage of her husband cheating on her over and over and over. We never saw her again. I hope she took him for all he was worth.

2. The Suspicious Client

u/mrhelmand: The job was given to us by another agency. It was for that evening (an important detail as it meant we did not have time to screen the job and get all the details we would typically ask for).

The brief was that the client suspected her husband was having an affair with a co-worker (he worked at a hotel in a capacity I don't recall).

We sent two agents to monitor him at work, requiring several hours of effort, while putting more on the expenses tab as the team had to keep buying drinks to avoid raising suspicion.

The client would call for updates every 20 minutes despite being told not to make contact and that a full report would be issued in short order.

The agents managed to tail the individual until the end of his shift (seeing nothing unusual) and discreetly followed him home, deciding to give the client a ring and confirm the address he had come to was his house and not the co-worker he was allegedly cheating with. The client evaded the question and demanded the team return to the hotel.

Confused and irritated, the agents returned and were greeted by the sight of the client scrambling out of a bush, binoculars in hand, directly opposite the hotel where, judging from the state of her clothes, she had seemingly been most of the evening.

Furious, the agents questioned her, and it transpired the man they had been watching wasn't her husband but rather someone she had been involved with casually who was no longer returning her calls.

Stern words were had (and management even talked about bringing in police), and we blacklisted her. She did, however, pay promptly and in full. There are many more stories, some funny, some strange, but that is definitely the weirdest.

3. The Mean Grandmother

u/baneofmyself: My uncle was a P.I. for a little over six years while going to law school. He once received a case from a man who believed that his mother might be trying to cause lethal harm to his children when she babysat.

He believed this because, as a child, his parents regularly beat him and his siblings. When he finally moved out and in with his girlfriend, his father exclaimed that he would learn the hard way (what he would learn, I simply can't recall).

Anyway, when he had children, his mother very openly spoke of her dislike for his wife and her kin, which scared the client.

My uncle spent nine weeks collecting evidence that partially confirmed his client's worst fear. His mother would discipline the children in ruthless ways. Some of the evidence he collected was footage of her beating the kids and doing terrible things to hurt them.

To make the rest of the story short, he reported his findings to both the police and CPS before getting permission from his client to pick up the children and take them to his apartment, where the police, the client, and my uncle would meet.

The client's mother was arrested and stripped of any rights to see the children, and her son filed a restraining order against her. He ended the story there, so I'm unsure if and/or how long she was imprisoned.

4. Keeping an Eye on a Nurse

u/VenBede: Did surveillance on a nurse. She was supposedly so disabled that she couldn't work. They suspected she was working.

It was the easiest surveillance I ever did. I arrived. The woman got in her car ten minutes later. I followed her, with no complication, to a strip club, where she went in and began doing her thing.

The club had a posted prohibition on video. So, I had to go in and watch her dance to 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 as compared to when she was nursing.

5. No One Remembered Him

u/mgdmw: 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 case that really made an impression on me was when a person had a fatal vehicle incident, and a claim was made that it was a workplace injury. I don't know what 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, many struggled to remember him. This 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 to that town but couldn't find the wife. She wasn't at any of the addresses 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, and it turned out to be the wife's parents. They called their daughter, and she arrived. Then, the mother and daughter cried while showing me all their photographs of the guy.

It was very moving, and I was so relieved to have actual 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. Usually, he would travel to the caravan on a Friday night, but this particular weekend was Mother's Day. He stayed Sunday night and traveled on 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 hear what happens to a matter, so I only hope it is finally settled.

6. My Strange Roommate

u/CyberTractor: Not a PI here, but someone who was confronted by one and told it was the weirdest thing he has had to do.

A roommate I had in college was a strange guy. This guy came from the other side of the country. He went out at all night hours, never showed up for class, slept during the day, and drank more energy drinks than was 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 first-year students live makes an adult who isn't janitorial staff stick out like a sore thumb.

So, I quickly learned that this guy was hanging around the dorms. I thought he was just cruising for some first-year student, and I 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 roommate's parents to trail him because his parents were concerned, and he wanted to ask me about my roommate's dorm habits. We then left for the coffee shop to talk about my roommate.

My roommate apparently liked to walk on the beach at night for stupid amounts of time, hang out at Steak and Shake, play games on his phone and Nintendo DS for hours on end, and cruise thrift shops for some reason.

I told the guy that my roommate just slept and didn't even have any personal things in the room besides his clothes.

The PI and I realized this kid 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 ever ever seen.

To explain the kid's actions, college was the first alone time he has 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. He ended up being a cool guy once he realized he was not in his parent's grasp anymore.

7. He Wanted to Find His Father

u/RoryDeanWinning: When I was a spunky teen working in my dad's PI office, a kid with a crush on me paid me good money to find his dad (who had a crazy common name).

It turned out his dad was now a woman living just a few miles away from our corrupt small town. He still had an awesome car, though.

8. Someone Went into Her Condo

u/DoktorInferno: I had a case referred to me by an attorney I worked for involving a woman who was convinced that her condo maintenance man was going into her home while she was gone and moving things around.

She had bought the condo from him originally. In other words, it was his former condo. I met her to discuss the case, and she seemed rational.

She was an attractive older woman, and the guy would obviously be familiar with the condo layout and would have access. I've seen weirder things, so we proceeded.

She agreed to let me install a hidden camera setup with a motion detector. She would call me if anything happened to make her think he had been there.

A couple of days go by, and she calls. I go by and get the tape (this was before digital recording) and check it out. There's nothing on it but her. I meet her to tell her this, and she says, "He must have some machine that makes him invisible. He's a space alien, after all." She had never mentioned this vital tidbit of information.

I told her that that level of technology was beyond my ability to deal with and that we should discuss it with her attorney to determine the best course of action going forward.

I called the attorney to let him know that our client had some issues, and we were able to get her some psychological help. But most importantly, her check was good.

9. Getting the Briefcase

u/NedTaggart: My brother was a PI in the early 90s. He worked for a law firm. I was in my early twenties, so he got me a gig as a process server.

He was working on a particularly nasty divorce case. The husband was a Jordanian national married to an American woman (one of several wives) who was over being the broodmare 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 took it back to the attorney's office, and he called the lady and said he had it. She gave him the combination. He opened it, and it was full of technical plans from Boeing for the Apache helicopter.

The attorney was shocked and shut the briefcase. He told me and my brother to leave, so we did. We never heard anything else about that case other than he contacted the FBI over it.

10. Back Injuries

u/bojangles001: I worked for a PI company that mostly handled workers' compensation cases for insurance companies or other employers.

I was assigned to a case in Seattle where a guy was claiming an upper back and shoulder injury. After a few hours on-site at his house, he pulls up in a truck and empties the truck bed of landscaping equipment ALONE.

After he has put everything away, he walks over to the side of his neighbor's house, pulls out a piece of the siding of the building, withdraws a pipe, and smokes it in front of me, all on camera.

In another case in Texas, I was following a guy (back injury) to the mall, where he met up with a woman who was NOT his wife (I had already identified her the previous day).

I followed them as they shopped around and then back to his vehicle, where they proceeded to get intimate in the car IN THE MIDDLE OF THE MALL PARKING LOT! I filmed it, of course, but I had to call my boss to ensure I could send this to the client.

11. The Case That Made Me Quit My Job

u/Kryimsson: It was one of the last cases that I worked on. It was for a child custody/paternity case. This case was the one that made me rethink what I was doing, and I got very disturbed by what I was asked to do. This is the case that made me stop being a PI.

Our client was denying that the child in question was actually his and was fighting the child support case. He believed that the mother of the child was a serial adulterer.

So much so that he spent THOUSANDS on the case for us to make sure there was evidence to support his claim.

The icing on the cake was when my case manager told me the client wanted video evidence that the child did not look like him. The client told us that we had to record the child at play.

So here I am, besides a playground, in an entirely limo-tinted car, videotaping a 9-year-old. I couldn't have felt worse about my life choices.

To this day, I have never felt like such a creep before. I hated that case and the case manager. Two weeks later, I handed in my resignation.

12. Threatening His Friend

u/davevr: A criminal was serving 20 years in jail for hiring a hit man (who happened to be an undercover cop) to get rid of his friend.

In prison, he came into some money and hired us to prove he was innocent. His plan to do this was to have us tell his friend that he better recant his testimony, or else our client would use his new money to hire a hitman to end his life "for real this time." This criminal genius told us this plan on a recorded phone call from jail.

13. The Invisible Neighbor

u/davevr: A guy calls me to help catch his neighbor who is knocking over his trashcans at night. We set up a small night vision camera to catch the guy.

We watch the video the next day and realize it is the wind. The client freaks out and says that his neighbor could have had an invisibility field or could have been moving too fast (like the Flash) to show up on camera.

He wants to pay us thousands of dollars to rent a heat-seeking camera or one that can shoot thousands of frames per second. It turns out lots of crazy people call PIs to investigate the TV controlling them, alien abduction, etc.

14. The Missing Girl

u/HelloWaffles: This girl's family once tasked me with tracking her down and convincing her to return to the family farm.

It turns out she had moved to LA, become a star in inappropriate movies, and married an apparent millionaire, but it gets weirder: some of her friends tried to ransom her when she went missing.

The husband, who didn't have money of his own, pretended to pay the ransom with money from his daughter's charity while giving the bag man a fake ransom to make the handoff and pocket the money from the charity.

Unbeknownst to the husband, his daughter actually hired the bag man to figure out what happened to the girl and the money to get it back, and he figured out the husband took it just as the girl got back from visiting her friends, unharmed. It was crazy.

15. Faking His Death

u/GhostonaRune: I vaguely remember a story a PI told me about a guy who faked his death and disappeared. His car was found at the bottom of a river. There was a brick inside the wreckage of the vehicle.

The insurance company said that since the guy was a business executive, it was highly unlikely he'd be driving around with a brick in his car. They refused to pay.

16. He Thought No One Would Know

u/million_monkeys: I'm a paralegal who investigates the backgrounds of witnesses for our cases. I found someone who was pretending to be someone else who died as a kid.

My boss alerted the Feds, and they investigated and found out he had faked his death 20 years ago to avoid an embezzlement trial.

He got convicted for a false identity because he filed taxes under a fake name. Not sure about the original embezzlement charge. He was a witness in a financial case involving the SEC, by the way.

17. The Fire

u/Vertoule: Obligatory "not me, but a coworker" tag. When I worked security, we had mobile guards who would come and do relief for us.

One night, my relief was late, so I called in, and dispatch told me to hang tight as they were occupied and would be there when they arrived.

I'm pretty easy, and it was a chill shift, so I said, "Okay, no rush, as long as they're ok." Dispatch chuckled and said, "You're in for an interesting story when they get there."

So, an hour and a half later, relief shows up with a coffee to apologize for being late (no biggie, but I appreciate wake-up juice). She tells me the story.

She was doing a routine check on a business we monitored when she noticed two guys trying to cut the lock with a cutting torch. She called the cops, and while she was on the phone with the police, there was an explosion.

The business was a mechanic, and I guess there was a small fuel leak from a car in the shop, and the sparks from the torch lit it, blew the door off its hinges, and set the place on fire briefly.

The guys were tossed like 20 feet, slowly scrambled to their vehicle, and took off (she got the description out to the police, who later caught them at the hospital where they attended for the burns they received).

Fortunately, there was minimal damage to the business. Nothing caught major fire, and she put out the small fire with a fire extinguisher. It didn't make more than a small blurb in the news, but it was an interesting story.

18. My Grandmother Hired an Investigator

u/albatross138: Not me, but my grandmother hired a PI back in the 90s to catch my grandfather cheating.

It uncovered he had been cheating with multiple other women, and he even had a daughter with another woman who is the same age as my mother (who is the middle child of 5).

19. Finding the Biological Mother

u/MjolnirPants: I briefly worked for a PI when I was younger (like 19). Getting the job was a funny story itself. I was walking past the office, which is in a tiny strip mall smack in the middle of a residential neighborhood.

On a whim, I decided to go in and see what an actual PI's office looked like. It was pretty unremarkable, except for the huge biker sitting at the only desk in a polo shirt and slacks.

We got to chatting, and I asked if he was hiring. He laughed and asked me what kind of work I was expecting. I told him, "Probably a lot of boring work sifting through papers in the library and courthouse."

He laughed again (he did that a lot. We called him Santa because of that and his white beard) and gave me the job.

I worked there for three months, during which we did a lot of insurance work. That mainly consisted of sitting in a car, reading a book, occasionally taking pictures of some guy in a neck brace or leg cast walking to or from his car, and two or three times taking photos of a guy playing baseball or basketball in his back yard.

But Santa also had a much-reduced rate for tracking down biological parents/siblings/children. We had one case where this woman in her thirties wanted to find her bio mom.

We went on our usual course, visiting courthouses, city halls, and libraries to track the biological mother down. We spent a whole month on it (we also worked on other cases during that time), which was a bit longer than usual, as the woman didn't know her mother's name, only her adopted parents, who had passed years ago.

The woman didn't have any adoption paperwork and didn't know where it would be filled (this was in the 90s when not everything was digital).

I finally found the adoption paperwork in a courthouse in the next county and got a name. I was running late (Santa didn't let me work overtime), so I made to drop off the copies of the paperwork at his office and go, but the guy stopped me before I could leave.

He was all excited by the mother's name—it was his wife. His wife had given up a baby for adoption 30-something years ago.

He called his wife, who dug up her copies of the adoption paperwork from back when, and sure enough, it was a match.

We called the client, who didn't answer, then went and picked up his wife and drove to the client's home. She's on the phone with her adopted sister, talking about our effort.

The PI and his wife immediately hugged the woman, who was very confused. Both were too emotional to get the words out, so I explained that the woman was her bio mom and the PI her husband.

It was a beautiful scene. That memory is one of the things that has kept me from turning bitter over the years. It was enough to put off my then-imminent loss of faith in God for another decade, knowing that this woman had hired her bio mom's husband to find her bio mom.

20. The Babysitter

u/dewayneestes: We had a babysitter we thought was stealing from us. Luckily, our neighbor was a PI couple, and they ran a background check for $10.

The babysitter had a string of DUIs, and a few days before a hefty fine was due, my camera disappeared. He also stole money from my kids' piggy banks.

He sort of disappeared but was also really into Instagram, so I secretly followed him. He started babysitting again for a single mom (easy target) and posted many 'fun' pics with this family.

I tracked down the mom and sent her a long email detailing his scam. She said we were right, and it was clear he had been stealing from her business.

He has since gone underground, but I still Google him regularly to see what he's up to. He's been able to avoid arrests for a while now.

21. They Mistook Me for My Brother

u/Fr1dge: I have a story about private investigators doing a hilariously terrible job. So, years ago, my brother injured his back at work because of his employer's unsafe work practices.

During the ensuing suit, my brother's lawyer was given a folder of documents from the employer's team. It turns out they had hired a PI to investigate my brother to prove that his injury was faked.

Well, unfortunately, the PI had been taking pictures of ME operating an ATV-mounted leaf hopper. My brother entered the court hearing and watched the color drain from the opposing lawyers' faces when he introduced himself, looking nothing like me.

22. I Wanted to Find My Mother

u/crayzcheshire: I hadn't heard from my mom since I was about 15 because she was very unstable due to drugs, etc.

When I was 29, I decided it was time to find out what happened to her. I figured if she was a Jane Doe somewhere, then I could put her to rest, and if she was alive, then I wanted to let her know that I forgave her.

I hired a PI to help. I guess my story moved her, so she also ran information for the man my mother was apparently married to (on the house). And with one clue from his report, I could track them down.

I wouldn't have found my mom (alive and just starting on recovery after being homeless for many, many years) if it wasn't for the PI who kindly ran an extra report for free.

Mom has remained sober now for about seven years and is probably the healthiest she's ever been, physically and emotionally.

23. My Sister Was Concerned

u/KoKeNo: My sister hired a PI for her child support/custody trial. She wanted to dig up some dirt on the guy, I guess (The baby girl was months old).

The baby's father made very good money as the owner of an HVAC company but didn't have a place to stay. He stayed in his warehouse. My sister's concern was: what does he do when he has the baby?

It turned out that when he had her, he would rent rooms out in really nice hotels for stays. He'd spend most days walking her in the parks, having picnics, and driving to non-local destinations like state/regional parks and zoos.

I got to see some of the pictures. A big 6'3", 300lb stocky body builder type guy, solo, pushing a stroller and diaper bags in tow, looking like his daughter was the only thing that mattered. The man is genuinely a good father with social anxiety issues.

24. Keeping an Eye on the Injured Worker

u/caverndiver: I worked for a law firm that routinely hired PIs to investigate worker's compensation claimants. One particular juicy case involved a guy claiming a major back injury.

PI got a whole day's video of him doing a roofing job. He was hauling big packs of shingles up a ladder and things like that.

They went to mediation, ready to drop the video on this guy when he showed up in a wheelchair being pushed by his twin brother. The PI had been following the twin all day. It was the fastest check I've ever seen written by an insurance company.

25. Exposing a Senior Manager

u/ThanklessTask: My old work hired a private investigator for an ex-senior manager, hoping to ruin him or something (horrible, bitter company).

Anyway, they got excited about his meeting with a younger woman, drafted the letters saying they'd expose him, etc. All very sordid.

Until they found out it was his daughter, he was meeting during her lunch break. Some people truly only see darkness.

26. My Brother Hired a Private Investigator

u/Pepper_in_my_pants: My brother hired a PI against me. And then, when the PI couldn't find anything, my brother wanted me to reimburse him for hiring the PI because "I misled him into thinking I was hiding something when I said I wasn't hiding anything."

27. My Friend's Stepfather

u/Dchung0217: Not me, but a friend hired a private investigator because he was suspicious his stepdad was being unfaithful to his mom. So, he asked me, and I put him in contact with a guy I knew.

A bit of a backstory—the stepdad is 5'10" and about 160 pounds. My friend is 6'2" and 235 pounds, ripped. At 15, when my friend's mom and stepdad started dating, my friend gave the typical "you hurt her, you're dead" speech.

Also, his bio dad walked out on him and his sister when my friend was like 4. It took a while, but my friend warmed up to the guy, and he's a good guy (he took my friend and me to a 49ers game once, which was pretty cool).

Anyways, the PI said he wasn't cheating. Apparently, there was a house on the market that my friend's mom wanted, and he bought it.

He had been remodeling it for some time, and he had kept it a secret. He bought it as a fifth-anniversary gift for her. Anyways, they live in a five-bed house now.

28. Find My Dog!

u/Trainwreck071302: My little brother hired a PI to find his dog. He was living in L.A., and his complex let the dog out by accident. It was a small dog, some mutt of toy breeds.

He looked on his own for two weeks and was devastated. My folks found this guy in Indiana who was like $3k to hire, but he guaranteed he'd find the dog, or he wouldn't get paid.

My folks and I chipped in as my brother couldn't afford that. The guy found my brother's dog in a day. It was crazy.

29. The Lady Who Didn't Want to Leave

u/maxpowersdb: I worked as a PI for about a year once when I was much younger. This wasn't a case I took, which will be evident by the end why I didn't.

We had an office on the ground floor of a building near the county courthouse with a door that opened to the street. This meant we got a fair amount of foot traffic.

If I had nothing going, I closed the office around 5 p.m. Around 4:45 p.m., a lady comes in asking all the usual questions. "Are you REALLY a PI?" "What cases do you take?" "How much do you charge?" I spent 10 minutes going through all that.

This lady seemed pretty wound up, which is not unusual. People don't come in looking for a PI when everything is great. Often, it's because they are having one of the worst experiences of their lives and are desperate for help and haven't gotten it elsewhere.

I asked her to tell me what brought her in today and be as detailed as possible. She told me that someone stole her ideas, and now she's being followed.

I thought, "Great, potential intellectual property case." I asked her to start from the beginning and tell me what those ideas were. She started telling me about her last gynecological exam. I immediately stopped her and asked her what this had to do with her stolen ideas. She flipped out.

She began screaming about how the doctor implanted a listening device inside her, and that was how they were stealing her ideas. I did my best not to react.

She screamed, "You don't believe me either! But I have proof!" She ran out of the office and returned a minute later with a large envelope. She pulled out X-rays of her pelvic region and shoved them in my face.

"See! Right there, that white spot on my ovary, that's the listening device!" I agreed that there was a small white dot but told her I was not a doctor or an expert in listening devices and couldn't confirm that it was one.

In reality, it didn't look like anything to me. I know it wasn't an electronic device of any kind, let alone one that could capture your ideas and transmit them to vans that were following you around now.

She then told me how the doctor was in on it, and they were stealing her ideas and making them into TV shows for Telemundo. This was the part where I tell you this middle-aged, blonde-haired, blue-eyed lady didn't speak a word of Spanish.

I asked her about the vans that were following her. They were different colors and often different drivers. But they were following her around, and that was how they collected her ideas.

I was looking for a polite way to tell this lady I wouldn't take her case, but she didn't slow down and insisted I do something about it. I finally caught a break. I told her the retainer amount I would need to get started. She responded, "Well, I don't have that kind of money. When we win in court, you can have half the settlement."

In the state I live in, only lawyers can work on contingency. Meaning their payment is contingent on them winning the case. PIs and all people that might work for these lawyers still have to be paid no matter what. I told the lady this.

I thought she was about to explode. I told her I couldn't break the law, but if she were to find a lawyer willing to take up her case, I could work for that lawyer as their PI.

She calmed down and said thanks for hearing her out. I said, "No problem." I asked her if there was a family member she could call or a doctor she did trust that she could see. She told me she was not crazy and stormed out.

I felt horrible for her. She was obviously living in terror and needed professional help. This was the first time I encountered the seriously mentally ill.

In retrospect, I should have called the police and tried to have them intervene. I regret that. I can look back now and cut myself some slack for being young and caught alone and off guard, but I still wish I had done more.

At the time, I just wanted to get her to leave peacefully. That was the most bizarre thing that ever happened to me during my time as a PI, but there were a couple of close runners-up.

30. Visiting the Motel

u/[deleted]: I've worked on a few bizarre cases. Once, there was a worker's compensation case I worked on.

I was told to get a film of this older lady who had supposedly been on total disability due to a severe ankle injury. She lived in a motel in the middle of nowhere in Pennsylvania.

The motel was called "Johnnies." I looked up the place online and found reviews of it on Google. There were horrible reviews, including one that said the business was mostly run by the owner's son, who had an addiction and would ask people who stayed there if he could buy any prescription drugs they had. That isn't sketchy at all.

So, I showed up at this 'motel,' which looked like it hadn't been renovated in 40 years. It was a small motel that had about 14 rooms.

I have no idea what room the person I'm supposed to find is in. I figured I should talk to someone at the front desk. There is no front desk.

The office part of the motel looked boarded up. But next to it was one of the motel rooms, and in the window of the room was an "Open" sign. On the door was a sign that said "office" and instructions for long-term hotel customers on where to drop their payment.

There was a doorbell. I rang it and waited. The guy who opened the door looked precisely like Kenny Powers from Eastbound and Down. He was wearing a Ninja Turtles T-shirt and Hawaiian shorts. He tells me to come in.

I walk in, and what I walk into is just a room with one desk. Nothing else. There was shag carpeting, dark-colored walls, and a lava lamp on the desk.

I realize this was the owner's son, Johnny Jr. I give him some fake story about how I'm an insurance adjuster looking for this lady. He then replies, "Oh, Mary? She lives in the room next to me. Want me to go get her?"

This is a problem because I have absolutely no backstory on what to tell this lady. She was repped by an attorney, and she likely knew a PI might be looking for her. I told him, "No. I just needed to confirm she lived here," and bolted.

Now, I park in the parking lot with a view of the room Johnny Jr. pointed at. A couple of hours go by, and then some old guy is standing near my car, getting stuff out of his car. Johnny Jr. walks out and starts talking to him.

I realize the older guy is Johnny Sr. They are literally standing right next to my car, and I can hear everything they say. What proceeds to happen is they start talking about me, well, at least the "insurance adjuster" who visited earlier.

Johnny Sr., having seen some terrible things in his day, immediately says, "That wasn't an insurance adjuster. That was a PI. Insurance adjusters don't work on Sundays." He tells Johnny Jr to ask Mary to watch out for a PI who might be in the parking lot.

My car is tinted. I think I'll be fine. Except, the parking lot I'm in is shared with a diner. The diner's owner comes out and starts talking to Johnny Sr. I had parked in front of a shed that the cleaning staff for the motel used.

Johnny Sr. now starts talking to the diner's owner, asking her if my car belonged to any of her employees or the people in the restaurant. She says she'll ask, and she leaves.

Johnny Sr then goes into one of the motel rooms where he lives. He constantly stands in the doorway, looking at my car. I left as soon as he turned the other way.

I would come back later in the day and would get a film of the lady I was supposed to watch. She was totally faking her injury.

Johnny Jr and his girlfriend came out a couple of times and tried figuring out what cars might be a PI's car. But because they saw my car earlier that day, they didn't seem to suspect it as suspicious.

Working as a private investigator sounds interesting, but these folks often go through unusual things while working on various cases. Have you ever interacted with a private investigator? Or has one of your friends ever hired one? We would love to know about your experience.