Sometimes you get the best of both worlds, by working a job that you enjoy and learning new things that are interesting to you.
But a private investigator may or may not fulfill that criteria.
Redditor Forgetadapassworda asked:
"Private investigators of Reddit, what is the most interesting thing you're encountered on the job?"
Tracking Cheaters
"My work partner and I were watching a guy who was cheating on his wife. We were at a restaurant where they were eating dinner together. We snuck over to his car to put a GPS tracker underneath the fender."
"At the same time, there was another PI team working to put a PI tracker on the girlfriend’s car, lol."
"We never made contact with the other team, but we sort of gave each other just a wink and a nod. Turns out, they worked at the same hospital and were each cheating on their spouses with each other (with spouses who were each suspicious of them) but were also cheating on each other with multiple other people."
"It was a hot mess and a lot to keep track of."
- Pocketeer1
Bottomless Pit Of Questions
"A mother hired me to look into the new boyfriend of her daughter, who was way older than she was. She said there was just something off about him, and she was right."
"They broke up in the middle of the case, so it got cut short, and I never got to the bottom of everything, but he had, like, five different current addresses (some apartments and some private homes) all in different cities, and he had multiple cars registered in different states of which none of the plates were coming back as registered to him or a family member (in fact, one of his trucks was registered to a dead couple he had no affiliation with)."
"I also ran a vehicle sighting report, and one of his cars was all over the place in, like, three different states over the course of a year, spotted parked in the driveways or random homes he had no seeming affiliation with. Very weird."
"I still wonder what I would’ve found if I kept digging."
- Emotional-Count-8595
Lied On His Résumé
"Worked with a PI every once in a while as a second car for surveillance. Surprised me how many people live off lies. Con artist types and scammers, renter scams were very common."
"Employee theft is also very common; we found that employees from a popular drink company were selling pallets of product on the side. The scam was pretty elaborate to account for the missing product."
"There were a couple of cases of husbands who traveled a lot for work had multiple families, as in another set of wife and kids."
"Found that a young, rich woman's fiancé not only didn't go to the college he claimed but actually had no degree at all, no job at all, no income at all. Dude would leave the house in a suit and tie and spend most of the day in a diner reading newspapers. Crazy how long he lived off her without her knowledge."
- TotallyCustom
A Likely Story
"Former PI, about 30 years ago. For me, the number of people faking disability claims was huge. It made up at least 70% of our cases, but it was also easy to prove... way more than other types of cases."
"Normally, we'd just hang outside their house and wait for them to take groceries out of their trunk, walk down their porch steps, etc."
"But one hilarious case that I will never forget was the one where a man claimed he hurt his shoulder and lost movement of his right arm as a result. We waited outside his house, and on day one, he came out and got into his car. So we followed him... to the batting cages where we recorded him swinging a bat all day."
- ImprovementFar5054
Broken Boundaries
"I was living in Tokyo. Someone posted an ad looking for someone to do some investigative work. I was broke and interviewed for a job despite not knowing anything about private investigation."
"A Japanese woman who spoke good English had a crush on a white guy. She wanted someone to investigate where he hung out, then befriend him, then introduce him to her."
"I declined the job. But later on, she hired me to do some marketing work for her. Unsurprisingly, one of the worst marketing clients I ever had, purely because she didn't respect boundaries. Shoulda seen that coming."
- thesecretmarketer
Very Suspicious
"I was a fraud investigator for a finance company. I went to interview a small business that we had lent to. I got there first thing in the morning."
"I walked in and had just introduced myself when a dude walked out of the back with a black clean sack. He got a shock that I was there, dropped the clean sack, and bundles of cash just fell out and onto the floor."
"I said quickly that I wasn’t there for that, and they needed to pay for the equipment they had secured and not paid a cent for. It was paid before I got back in the office."
- Salami_sub
"Was... was it paid right out of that sack to you?"
- iAMguppy
Too Hurt To Work
"I worked as a PI for nine months, and the company I was with investigated employee workers' comp fraud."
"I'd follow people who supposedly had injuries so debilitating they couldn't work, and then film them doing things like carrying three jugs of detergent through a grocery store, or lifting a massive concrete tortoise out of a garden bed and moving it to the other side of the yard."
"The most interesting thing was a job I did in another state, and I filmed a guy about a mile away in a farm field slowly take apart a small plane he had sitting in a field over a period of eight hours, when he supposedly had a back injury so bad he couldn't lift 10 pounds. Maxed out my camera memory, ended up taking pictures for the last 4 hours every time he moved a piece of the plane."
"Small piece of advice: if you're committing workers comp fraud and the company's insurance tells you to go to a specific doctor... they have paid PI people to wait for you there and follow you home/around for the day. They wanted to get you in a specific place to be followed after you pretended to be hurt, so they could show that you went and did things you shouldn't be able to."
- Tee_Hee_Wat
In Liew Of Nancy Drew
"I heard of this story about a girl from my uni before. She started suspecting her dad of having an illicit affair, so her friends decided to channel their inner Nancy Drews and started following the dad around. After a couple of tries, they eventually found him meeting up with the same older woman repeatedly. She was devastated."
"One day, she decided that she was going to confront the two of them, but didn't want to make it into a public spectacle. She decided to follow them to the woman's place. She was so confused because she was following them back to her own house."
"Turns out, the dad bought the mistress a house on the street right behind theirs. The dad also has another daughter, two years younger than her, and named the daughter the exact same name as her."
- BloomingAtDusk
Personality Unclear
"I was slightly involved in an investigation by a private investigator. Involved in that he contacted me twice. First, by 'accidentally' getting gas at the pump next to me in a not too new, appropriately dirty truck and starting a conversation about hay that led to him eventually asking indirectly about the subject of the investigation, who was a not too close neighbor."
"My impression at the time was that he was a slightly awkward, but friendly, person just trying to get some feed for his animals."
"A few weeks later, he stopped by my farm. Different personality. Polite, efficient, and direct, driving a typical fleet sedan. Mentioned the previous encounter and explained he was conducting an investigation, which was complete. He was just following up to see if I had any comments about the guy in the event it went to court."
"Turns out he was on disability due to painful neck and back injuries that caused weakness in his arms, rendering him unable to work as a plumber. Selling hay in 80lb bales, which he was recorded throwing onto a wagon several hundred times over the course of the investigation."
"The investigator was impressive. My first contact with him left me thinking he was totally harmless. My second showed him to be a competent person. It was an interesting experience."
- Uncanevale
Chronic Vandalism
"True story. Hired to watch someone who had been the victim of repeated, serious vandalism. Because of reasons, it was thought to be related to drugs or organized crime, possibly a scheme to sell protection."
"What we found by watching the victim was tons of drugs, organized crime connections, and revealed the mayor of a small city to be having an affair with someone well connected to the drug trade. As to the vandalism, an ex-boyfriend was eventually caught in the act; it had nothing to do with the drugs and crime."
"It was a very small city, if you're not from the area, you've probably never heard of it. My memory is that the mayor was eventually outed for the affair a few years later and that neither the city nor local media really cared; small city, basically a town. I think maybe it also wasn't much of a secret."
"All of the affairs and drugs were out in the open in public. We would only see things with some deniability, though. Things such as duffle bags being exchanged, we didn't know what was in the bags but the manner in which they were exchanged, by dead drop, indicated the contents were illicit."
- RocketCartLtd
".....Are you Jack Reacher?"
- toon_84
Just In Case
"A good friend was self-employed and had full insurance cover 'just in case.'"
"He did get injured while working and couldn't walk unaided for months. It turned out that his business owner's compensation insurance was subject to a very high percentage of fraudulent claims so a P.I. investigation was normal."
"Picture a street of a better class of middle-income houses. Good weather and my friend is working in his yard doing landscaping by sitting down and dragging his injured leg along."
"He did this for hours every day. Each day, at lunchtime, he would get up on his crutches, hobble over to the car where two investigators were watching and filming him, and offer them to come into his house to have coffee or a cold drink. Every day for three weeks, 21 days. They angrily refused each time."
"After the third week, the observations dropped to one or two spot checks each week for the months he needed to get back walking."
"We guesstimate the cost of the investigation was way more than the insurance payout."
- CurveAccomplished642
Disability Fraud
"We did mostly disability fraud. Most PI work is insurance because it’s consistent and easy to bill."
"It’s basically professional doorknob watching. Show up at site around 4:00 AM, sit there all day, and see nothing. Take time-stamped photo or video every hour. Sit in car all day peeing in Gatorade bottles and watching movies. Go home, submit report that nothing happened, and you saw nothing."
"Sometimes catch people claiming disability working out at a gym or cleaning gutters, basic normal stuff that people claiming disability shouldn’t be able to do."
"The weirdest thing I ever saw was a municipal client that wanted surveillance on a dude suspected of violating a zoning ordinance by manufacturing fertilizer in his house. Never confirmed any of that, but that would be stinky if true."
"Sometimes you have to follow the subject in a vehicle and that requires a crazy amount of traffic violations, mostly running red lights and speeding."
"Most contracts want you to break surveillance if you get noticed. You just switch cars and try again the next day."
"All things considered, awful job. Little career growth. Crazy hours. Inconsistent work. Licenses can be difficult to acquire, so mostly you work for a company that holds a license and never progress. You’ll miss holidays and family events. S**t retirement."
"If you think you like that work, be a cop and then make detective. At least you get a pension."
- Temporary_Anybody279
Arranged Marriages
"I’m obviously not a detective or anything, but when my best friend got matched with this girl for an arranged marriage, something about her felt off. Nothing dramatic, just a gut feeling after meeting her once. She was weirdly flirty with me the first time we met, and I couldn’t shake the vibe that she wasn’t taking things seriously."
"Me and another friend discussed about it and started casually keeping an eye out. Our offices were in the same area, so we’d see her around now and then. Eventually, we got in touch with someone from her workplace and started hearing she was supposedly having a thing with her boss. And yeah, the boss is married."
"We didn’t want to jump to conclusions, but the stories kept adding up. One weekend we got a tip and followed the tip, and yes, caught them at a beach resort 150 kms the city. Saw them hanging out by the pool, holding hands, and staying in the same suite."
"All this was happening while both families were planning the engagement, buying outfits, booking venues, the works. It was messy."
"We gathered the photos, messages, proof from the hotel guy by giving him some bribes, etc., and then shared it with my friend. At the next meeting with her family, he calmly showed them everything. The marriage was called off."
"Not proud of playing spy, but I’d do it again if it means saving someone close from walking into something like that."
- ResidentAd8536
All Grown Up
"A weird dad paid us thousands and thousands to watch his daughter during her first two years of college."
"Went to her tennis matches, friended her from various sock puppet accounts, ate at the restaurant she worked at, etc. Certainly not the strangest case or circumstances, but one where I’ve been tempted in the years since to reach out and let her know of the insane invasion of privacy."
- sock_____puppet
"Wild. Sounds like he was helicopter/paranoid as you don't mention her behaviour as warranting this scrutiny. I guess I can understand, but yeah, geez Dad, maybe lay off."
"After your PI is six months in and still saying, ' Uh, yeah.. your kid is normal and sane after leaving home. Sorry.'"
- Lithrae1
The world is full of questions and suspicion, and it's unclear what might be uncovered if you were to hire a private investigator.
But just remember, don't ask questions you may not want the answers to.
