The 7 Wildest Cheating Stories Ever—Straight From A Private Investigator

Photo credit: Massonstock
Photo credit: Massonstock

From Women's Health

Whenever a celebrity's cheating pics are plastered all over tabloids, the internet implodes. But for a private investigator, capturing an affair on tape is just part of a normal workday. And, unlike celebrities who can still afford expensive hotels and a degree of discretion, ordinary people have to get creative in keeping their extramarital hookups a secret, inevitably making for some juuuuicy stories.

So after years on the job, which incidents stand out the most to someone who's seen it all (or as close to all as possible)? Whitney Joy Smith, president of the Canadian-based Smith Investigation Agency, shares the seven most memorable affairs her team uncovered:

1. "This woman's husband said that he had suddenly found new friends. They’d all go to the gym, they all liked to be buff–that was his reasoning, even though his physique hadn't changed at all. So she called and we set up surveillance, but he was next-to-impossible to follow. He was so suspicious and drove weird routes, made abrupt turns, and so on.

We did notice one thing, however: The neighbor always left at the same time as the subject. When we asked the client if they had ever seemed flirtatious, she said yes. So we decided to follow the woman instead of the man. She was also suspicious and evasive when driving, but we came prepared with three investigators. After briefly losing her, we found her vehicle in an industrial location behind a gated area in a building that was closed for the evening.

Photo credit: Giphy
Photo credit: Giphy

Moments later, the subject's vehicle pulled into the same parking lot. I picked up the client in my car and we drove down to the location. We never bring clients with us–this was the first and last time [because] she would have likely shown up either way once she got the update. So at least her being in my vehicle made it safer for everyone.

As we were pulling in, she literally jumped out of my truck and hightailed it to the vehicle. She opened the back door and found him with his pants down and the woman undressed. She was hopping up and down, screaming, and she was trying to get at the neighbor, but the guy was standing in between them. He blocked the way so the woman could get to her car and we moved out of the way so she could leave safely.

[The couple] stayed together–I guess they tried to work it out and he stopped seeing the neighbor. She called some months later and wanted us to tap his phone to see if him and the woman were still speaking, but we don’t do that service.”

2. "One guy wanted us to follow his wife as she said she was going on a ladies' trip to a tropical island. She gave this grand story about all the things they were planning–it was some sort of bachelorette party with seven to ten women. The client knew the husband of one of the women, and had said, ‘Oh, must be fun, they’re going out of town,’ and the husband had no idea what he was talking about.

We followed her to the island, and the woman was partially telling the truth in that one female friend was there for three out of 14 days. As our investigator was in the lobby waiting for the friend to depart in a taxi, we saw the subject say goodbye to her friend. She then walked into the lobby, and the cabana boy walked up to her, picked her up, and they started kissing.

Photo credit: Giphy
Photo credit: Giphy

They certainly seemed comfortable with each other, it was all hugs and kisses–it wasn’t a first-time kind of thing. They spent the next week at a nearby hotel enjoying life, tanning, kissing and more by the pool. All the times the subject was sending pictures to her husband of her and her friend in different swimsuits to keep him in the dark, I was sending him the real images of her with the cabana boy.

From what we gathered after giving everything to the client, he looked through photos from previous times that she had been there and figured she had met him during one of those trips. [The client] was upset at first, but by that time, he had had a little time to let it sink in and settle. I think he knew it–it was just a matter of him being correct."

3. "This man and his wife had just had a baby only weeks before. The baby was crying a lot, so this guy’s excuse was he needed to clear his head. At first, she didn’t think much of it, but then she was like, 'What are you doing? You need to be helping me.' And he said he just had to go for a drive. So that’s when she hired us.

Normally, it takes a few days for us to find out what’s going on, but the first day we followed him, we tailed him to a popular university in Toronto. The subject picked up a young woman who was attending the university–he would’ve been somewhere in his mid-thirties and she would be anywhere from 18 to 22. They went to a nice restaurant where they held hands and kissed the entire time. Then after dinner, they went to the vehicle and, without tint on the car windows, began to fool around.

I don’t know if he and his wife stayed together–she was distraught when I told her what was going on, crying a lot on the phone, asking what she should do. Ultimately, we’re not there to give marital advice–we provided her with the evidence and I never heard back from her."

4. "A woman had gotten some sort of STI from her partner, and that was her cue that something was off. We followed the subject after he flew out of the province for business and tailed him to a hotel he was staying in.

Photo credit: Giphy
Photo credit: Giphy

We knew from the client that the subject was a heavy drinker and would most likely be in the bar area of the hotel. The investigator that happened to be on this file was a woman, and the subject, after hitting on several different women in the hotel, proceeded to hit on our investigator. After her multiple attempts to get him to move on, he left her a room key, just in case she changed her mind."

5. "This guy was in a long-distance relationship with a woman and thinking he wanted to get married. He had some money and didn’t want to go into a relationship where he could be taken advantage of.

We tailed her, and she would go shopping with a couple of girlfriends, or sometimes just one, and just hang out. But on one of the stakeouts, the subject and a man were at a local mall, where we were documenting them holding hands and kissing. While we went over the video to finalize the file for the client, we noticed that, while in the store, she was also stealing things from the cosmetics aisle and placing them in her backpack."

6. "We followed this woman looking to see what her activities were while her husband would travel for work–something just seemed off for him. She did a lot of shopping and spent time with girlfriends, but on two different occasions, we had seen this woman drive to multiple motels and hotels looking for a room. At first, the investigator wasn’t sure why she was bouncing around all these different places.

Photo credit: giphy
Photo credit: giphy

We later asked the hotels about what her inquiry was–and found out she felt the hourly rate for a room was too high. So, after going to approximately five different hotels, this woman stopped in a parking lot and jumped in the backseat with her lover–to them, I guess it just wasn’t worth the price for such a short amount of time."

7. "We were hired by a woman to find out if her husband was cheating. She had noticed some inconsistencies in his behavior in general–he said he was going to a sports bar to watch a hockey or football game, or he was working late or his car broke down. Even when she wanted to go away together for a long weekend, there was always some reason why he couldn’t.

After a few weeks of surveillance, we caught him spending time with another woman and had everything we needed to have more than enough proof of the affair. They ended up breaking up, but then, about six months later, we got a call from someone wanting surveillance. Sure enough, it was the same guy, and the woman he had the affair with now wanted to know if he was cheating on her. We didn’t end up taking the case, but she had given us the full rundown of the situation and from everything she explained, we knew it was the same man."

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