I’ve never had to do this before and I really hope I never have to.
That being said, I do enjoy hearing stories of other people who had to, because they can get pretty crazy.
AskReddit users shared their stories about what they ended up finding out from the private investigators they hired. Let’s take a look.
“My boyfriend’s family hired a PI to do some covert genealogy, because they’re white but all have thick wiry hair that only black hairdressers can handle. And because there are things older folks in these parts Just Don’t Talk About.
Turns out there’s a fair amount of Lumbee Indian (a community founded by disenfranchised Native Americans and escaped slaves back in the day) in boyfriend’s family, which explains the hair.”
2. The Best PI story.
“I used to work for an insurance defense firm years ago.
Best PI story I have is where we hired one to tail a guy who was suing our client for an injury that wasn’t entirely our client’s fault. The guy was refusing to settle, and was insisting on going to trial even though we offered a fair sum that would’ve paid his medical bills.
The PI we hired got some good pics that showed the plaintiff was nowhere near as “injured” as he claimed, but the crown jewel of the photos was one where the guy was walking on a pier with a woman who wasn’t his wife. Had his hand on her ass and everything.
Later in a deposition, the attorney slid the picture to the plaintiff and said something like “Mr. Smith (obviously not his real name), who is the woman in this picture? We would like to schedule a deposition with her as well.” The guy went ghost white and told his attorney he wanted to settle.
At least he was smart enough to realize that if his wife found out the other woman was gonna be deposed, he was gonna have to get a family law attorney as well, because the divorce papers would soon follow.”
3. Here’s the story…
“I had to hire one to help gather evidence to defend myself against an assault charge. The story goes like this:
Ex attacks me in front of a witness that I don’t know, steals my phone then calls the cops on me. I get arrested and she wipes my phone and steals some incriminating evidence from my place while I’m in jail. I get out and hire the PI to try and track down the witness.
The Friday before a Tuesday trial I finally find the guy and have the PI go to talk to him to avoid witness tampering. Guy refuses to get involved, so I think I’m f*cked, bc my ex is this tiny little girl who plays the victim all too well. I call up my lawyer to accept the plea deal. Turns out the prosecutor had barely spoken to the ex until that day.
Due to fortunate timing the prosecutor met with my ex before my lawyer could get ahold of them. The prosecutor realizes my ex is completely deranged, and also admits to having attacked me multiple times that night, destroying any case. I get the call – all charges dropped. Most relief I’ve ever felt in my life.
So, the weird thing was, the PI didn’t really help, directly, but working with him to find this witness kept me from accepting the sh*tty plea deal for just long enough for things to work themselves out.”
“My grandma’s older brother was kidnapped whenever he was under 10 years old (I cant remember exactly how old) from the state fair.
It was believed his uncle was the one that took him because his dad passed away early on and his brother wasn’t happy that my great grandma got custody and another man was raising his nephew. One day we were sitting out on the back porch looking through old photo albums when we came across a picture of him and my grandma told us about what happened.
About a year and a half to 2 years later her health went downhill. It was 60+ years since he was kidnapped and my grandma was a couple months from passing so my mom and aunt hired a PI who managed to find him.
He had been living in Brazil ever since he was taken and had an entire family down there. They got to reconnect over facetime and she got to meet an entire side of her family she didn’t even know existed. They talked on the phone and FaceTimed numerous times a week all the way up until she passed.”
5. Spying on the school.
“My mother hired one to spy on the school.
See, my little brother is dyslexic and has severe social anxiety, and so was struggling a lot in a public school setting. He had an IEP, which the teachers and principal were insisting was being followed. But everyday my brother would come home in tears shaking because he felt abandoned and stupid.
So mom hired the investigator, and sure enough the teachers were basically just ignoring my brother. They’d sit him in the back of the room and demand he do his work, then wouldn’t help him through it. Then they’d yell at him because he didn’t do it (again, he couldn’t write because of the dyslexia).
With all the evidence, my mom was able to arrange a meeting with the school board and threatened to sue. They agreed to pay his tuition for a private school that was supposed to help. It didn’t, and mom ended up just pulling him out and homeschooling him. He’s been doing a lot better.”
“My uncle disappeared without a trace in the 1990s, about a year after his daughter was kidnapped and murdered. We hired a PI to track him down, and the PI found next to nothing.
As my uncle had developed a hero*n problem following my cousin’s murder, the best guess the PI had is that he had died by OD or suicide, and that his body hadn’t been found or he was reported as a John Doe.
Imagine my family’s surprise two decades later, when my uncle calls my mother, who is his only sibling. My grandfather had been on his deathbed for a month, and somehow the uncle found out. He arrived to make a show of paying his respects, in an attempt to get money out of his parents. When it was clear he wasn’t getting anything, he took off once again.
He never gave us a real or detailed explanation of why he left, where he’d been, and what he’d been doing. He left no address or telephone number and made no attempts to remain in contact.
The PI we hired must have been a sh*tty one, that or my uncle really knows how to disappear.”
“My work requires us to hire PIs to investigate injury claims.
We had a high schooler claiming a head injury so severe that he basically couldn’t live a normal life specifically, he had an issue with bright lights. Couldn’t stare at a computer or TV long etc.
Our PI caught him on several occasions at the movies, arcade, basketball games, etc. so basically he was making a fraudulent claim.”
8. Exaggerated injuries.
“I used to work for an insurance company that handled injury claims.
More often than not, the investigator would find nothing, or would give us a lot of video showing that the claimant was indeed injured (we would then bury the video of course).
There are, on occasion, people who are exaggerating their injuries but they are by far the minority. The few cases where that does happen has a way of placing unfair suspicion on the legitimately injured people.
My fave example was a time when the insurer sent me hours of video where they had followed this young, healthy-looking (and quite physically fit) fella around, leaving his house, going and working outside on a home renovation, doing lots of heavy lifting, carrying things up and down ladders. All this despite a reported back injury. The insurance adjuster was all gung-ho on taking the case to trial without making any offers.
Lo and behold, I look at the video, check the age of the claimant in the file, and think to myself “this guy looks awfully young for someone in his 50s”. Ten minutes of facebook research later, I work out that the PI had been following the claimant’s 25-year-old son for two weeks.
The few cases where there is actual fraud make for good stories and get told and re-told, but in reality the vast majority of claimants are on the level despite insurance company kool-aiders wanting to believe otherwise. I spent a lot of time having to talk them down while I did that work.”
9. A sad story.
“My family hired a PI.
My grandpa had a younger brother, I’ll call him John, that was always the black sheep of the family.
Apparently my grandpa was quite protective of John and would always defend him to family and friends, saying he was a good kid who would figure his life out eventually.
One day John asked my grandpa to loan him a couple thousand dollars to buy a house, which was no small amount in the 60s, and after talking it over with my grandma they eventually did. John skipped town shortly after that and never contacted my grandparents again. My grandpa, being the brooding Irishman he was, never really talked about John after that.
In the 1980s, one of my moms cousins was curious what happened to John and hired a PI to go looking for him. They lived in a small town in northern British Columbia, Canada, and after a while the PI found John living on the streets of Vancouver. My grandmother and my great aunt flew to Vancouver to see him, because my grandpa still wanted nothing to do with it, to see if they could bring him home.
My grandmother said when they met with John he was livid, absolutely f*cking livid, that they had found him. He was living with a small group of people that had turned into his little sort of street family. He told them he was very happy with life the way it was, to leave, and to never try to contact him again. And that was that.
My grandmother and my great aunt got back on a plane and flew home without him. To our families knowledge, lived out the rest of his days on the streets of Vancouver.”
10. Long lost brother.
“My grandfather did.
He was separated from his brother when the Japanese occupied China. My grandfather safely made it to Hong Kong and eventually to Canada. His brother made it to Singapore or Malaysia according to family friends back then. So my grandfather spent a good 5 years or so working with a PI to find his brother so they can be reunited.
Sadly, with just a picture and the fact many people died in the war, it wasn’t much to go on. My grandfather is still alive and always thinks of his brother. It’s his wish to see him one more time.”
“My Grandmother hired a PI back in the 1990s to catch my Grandad cheating.
It uncovered he had been cheating with multiple other women and he even has a Daughter with another woman who is the same age as my Mum (who is the middle child of 5).”
12. Seemed normal…
“When I met my wife, she seemed to have a normal modern family. Two moms, two dads. Over time it became apparent her step-dad wasn’t around much. Holidays, birthdays, you name it, he’d pop in to say hi, grab a nap, whatever, then take off again.
My wife’s family thought this was normal, just the way it had always been since they were teenagers. He claimed to have a job following FedEx trucks around the state to prevent theft and drug trafficking. But I thought it strange and started making jokes about him having another family.
Well, I guess it got my sister in law thinking because she gets a favor from the PI at her law firm. Sure enough, he has not two but THREE wives around the state, and five other (step)children between them.
My sister-in-law breaks the news to her mother who immediately changes the locks and files for divorce. They never speak again. Cold Turkey. Divorce is even uncontested. As a FU they also send the report to his other wives.”
13. The lost child.
“My Dad got my Mom pregnant when she was 15. Her Dad forcibly put the child up for adoption.
Nobody ever talked about it but I found out about it because my Dad became an alcoholic who would blackout and talk about what was bothering him. He couldn’t take the losses of his oldest Son, My Mom who cheated on him, and the death of my little Sister.
My (now) ex-wife decided that she wanted to find my older Brother but my Paternal Grandfather would not cooperate. She asked my Mom about it and got as many details as she could. I was against looking for him because he probably didn’t know that he was adopted and I didn’t want to screw that up for him. After she got my parent’s hopes up I agreed to hire a P.I.
The next day we had pictures of a guy who looks like my Uncle, a website to a small company that he had founded, and links to his profile for a lot of the high profile jobs that he’s had. We found out that he had been adopted by a college professor at what I would call the Harvard of the Midwest. The guy had a good life, much better than he would have had.
I gathered the P.I.’s report, pictures of his biological family, and some medical information that might be of use, and I sent him a package via certified mail. He never responded.
Years later I found out that he was divorced around that same time so I thought that maybe his ex didn’t give him the information. I joined FaceSpace just to find him. He was there with pics, so I knew that it was the same guy. I sent him a PM stating who I am, why I was contacting him, and why he had been put up for adoption.
I added the request that he would, at least, tell me to go to Hell or something so that I would have some kind of closure for my parents. His page went private and I never heard from him.
My Mom died a few years ago. She was glad to know that he was well, and successful but never got to meet him. My Dad is doing very well now but I know that it still eats away at him.”
14. Bad faith.
“My law firm had a bad faith insurance case several years ago. A guy had gotten hurt at work. He claimed he was disabled because he hurt his back, and could not lift anything or really engage in any type of physical activity.
His disability insurance carrier failed to handle the claim and pay him what was owed.
There was a potential for relatively large damages. In fact, the carrier filed in the court case what is known as an Offer to Confess Judgment. It’s a way of agreeing to let judgment be taken for that amount. The plaintiff can accept the offer or reject it. However, if he rejects the offer he is responsible for the defendant’s attorneys’ fees if the verdict ends up being less than the amount of the Offer to Confess Judgment.
The Offer in this case was $ 750,000. He rejected the offer.
A few weeks later our PI found out that the plaintiff bowled every week. The PI got video of the plaintiff bowling and copies of his score sheets going several years back through the date of the accident. It was clear he really was not disabled.
He also found that plaintiff had been in a car wreck and was making identical injury claims to the other driver’s insurance carrier.
We filed a motion with the Court to dismiss the lawsuit based upon fraud and perjury. The Court set the motion for a hearing, but before that happened the plaintiff dismissed his lawsuit.”
15. Keeping it a secret.
“A friend hired one 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.
Bit of a backstory, the stepdad is 5’10”, 160ish pounds. My friend is 6’2” 235 pounds, ripped. At 15, when my friend’s mom and stepdad started dating, my friend gave the 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 (took my friend and I to an 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 kept it a secret.
As a 5-year anniversary gift to her, he bought it. Anyways, they live in a five-bed house now.”
16. I forgive you…
“My dad hired a PI in the mid 90s in Eastern Europe to find out if one of his business partners was stealing from him. Instead he found out his own brother was stealing from him.
He refused to believe the PI and his brother robbed him blind. Took a huuuuuge amount of money and left him with gigantic debt. He still forgave him.”
17. Stolen car.
“Back in the ’90s my dad had a friend who owned a Renault Clio Williams and one day someone stole his car (the car was located in Athens).
So after reporting the event to the police he really wanted to get his car back (because it was expensive) and he hired a private investigator to find his car. After like a week he received a call from the investigator telling him that his car was located at a junkyard outside of Thessaloniki.
So he went at Thessaloniki and found his car, so he rushed inside a police station to inform them that his car is located at X location. Believe it or not the officer told him not to mess with the owner of the junkyard (this junkyard was known for stealing cars etc) and hope he will get his money back from insurance.”
18. We’re gonna need a refund.
“My sister (mid 30s) is adopted and hired one to find her estranged biological father.
They came back saying that not only was he still alive and nearby, but he had a daughter. Meaning she also had a biological sibling!
Further digging from the PI uncovered that they weren’t just similar ages either, they were exactly the same age. The evidence suggested that my sister had a twin and her birth father had taken the twin and vanished.
Huge, life-changing news.
Eventually, through more incredible detective work, the PI realized that the daughter was actually just my sister. There was no other sibling and they had just been investigating my sister the whole time accidentally. Needless to say, we asked for the money back.”
“My little brother hired one to find his dog. He was living in L.A. and his complex let the dog out on accident.
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 brothers dog inside of a day. Sh*t was wild.”
20. The babysitter.
“We had a babysitter we thought was stealing from us.
Our neighbor was a PI couple and they ran a background check. The babysitter had a string of DUIs and a few days before a big fine was due, my camera disappeared. He also stole money from my kid’s piggy bank.
He sort of disappeared but was also really into Instagram so I surreptitiously followed him. He started babysitting again for a single mom (easy target) and posted a lot of ‘fun’ pics with this family. I tracked down the mom and sent her a long email detailing out his whole scam. She said we were right and it was clear he’d 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.”
“My grandmothers first “boyfriend” after my grandfather died said he was a retired cop and a veteran. They enjoyed dancing to country music together, and bought a new car, in her name though, even though she can’t drive anymore.
My uncles hired a PI. Turns out, that old b*stard had a habit of shacking up with widows and bleeding them dry. (The boyfriend not the PI).”
“My grandfather once hired a PI to investigate my grandmother.
While spying on her from his car another investigator he knew came up frantically to his window and was like “what are you doing here!?” To which his response was obviously “What are YOU doing here?”
Turns out my grandmother was being investigated by the DEA for drug dealing. I don’t think anything came of it that I know of but we’re all pretty certain it’s the reason the old family barn was burned down. That woman if batsh*t crazy and this isn’t even the worst/wackiest story I’ve been told about her.”
23. Finding Mom.
“Hadn’t heard from my mom since I was about 15 (very unstable due to drugs and alcohol 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. Hired a PI to help… I guess she was moved by my story and so she also ran info for the man my mother was apparently married to (on the house).
And with one clue from his report I was able to track them down. I wouldn’t have found my mom (alive and was just starting out on recovery after being homeless and addicted 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 7 years and is probably the healthiest she’s ever been, physically and emotionally.”
24. Time for closure.
“My mother’s dad walked out on mom, my aunt, and my grandmother when mom was just 5. A few years later, my grandmother died of a grand mal seizure.
Mom was taken in by her grandparents, but she always wondered why her dad left and what became of him. In her 40s, she saved up a bit and hired a PI to track him down. Turns out he moved over time from Pittsburgh to California where he wound up in prison for armed robbery and so e other violent crimes. He died in San Quentin penitentiary.
I think mom got a lot of closure out of that. She was able to see that life would have most likely been even worse had he stayed. At least living with her grandparents, she was loved and raised to fulfill her potential.”
Have you ever hired a private investigator?
If so, how did it turn out?
Share your stories with us in the comments. Thanks!