16 Grotesque Cheating Stories That Are So Baffling, It'll Make You Retire From The Dating Game Forever

16 Grotesque Cheating Stories That Are So Baffling, It'll Make You Retire From The Dating Game Forever

Reddit user h3llofaRide asked people of the community, "What’s the worst cheating story you’ve ever heard?"

Oprah Winfrey meme: "That person's cheating, that person's cheating!"

Welp, folks were transparent as heck, and unfortunately shared some truly baffling stories. Like, the AUDACITY of people cheating on their partners like this...it's unbelievable.

Sarah Jessica Parker and John Corbett in "Sex and the City 2"

So, here are some of the absolute worst cheating stories that juuuuust might make you give up dating altogether:

1."My bio mom's best friend was diagnosed with Stage 4 lung cancer. We moved her, her husband, and her daughter in. My mom slept with her husband and got pregnant, so they put my bio mom's friend in a nursing home to die all alone. They did this just so they wouldn't have to deal with the consequences. She was hours away as well, so her daughter who was 10 at the time was unable to visit her. She died alone because she went to her 'best friend' for help."

"I don't speak to bio mom anymore. After her friend's death, she showed off her brand new car with the life insurance money (she ended up marrying her friend's husband).

At the time, her dead best friend also had a 19-year-old daughter who was without a home with a toddler. I felt so fucking sick sitting in the car listening to her brag about how she finally got the car she deserved...

Some people are disgusting."


2."My friend had a massive heart attack and having sex was hard for him for a while. He worked and his wife didn’t. He feel asleep in the chair one morning while getting ready for work. He awoke to a man unlocking his door. For about a year while he was at work his wife had different men with keys to the house coming over to have sex with her."


A woman holds a man from behind and gestures for silence by placing her finger on her lips in an intimate setting
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3."A couple was together for eight years. Both worked at sea on the same ship for eight to 11-week trips. They bought a house and were heading towards marriage and having kids. At the start of an 11-week trip, the guy noticed something wasn't right. His girlfriend had fucked a crew member on the trip and wanted to be with them instead. The guy had to watch the start of their new relationship while on a floating prison, and due to his qualifications, he couldn't leave the ship. The source? Me — I'm that guy."


4."There was a former colleague of mine in his mid-thirties. He was living with his long-term girlfriend, and they had been shopping for engagement rings. He comes to work one day and, in the early afternoon, receives a text from her telling him she’s seeing someone else, has packed up the house, and moved out to live with the other guy. No apology, no further explanation. She immediately blocked him and left him to deal with the rent and other bills on his own. He was a nice guy, so it was horrendous to see that happen to him. He’s happily married now to someone else."


A person wearing a white long-sleeve shirt is seen removing a gold ring from their left ring finger
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5."I was an IT contractor for the Department of Defense. We got a keyword alert on an email conversation, so we went and checked out the email and the email thread. It turns out it was a Senior Chief who was talking to nearly half a dozen women under his chain of command who he was having affairs with (multiple of which were pregnant with his children). He, of course, was married and had four kids with his wife. What started out with a, 'Hey, you're not supposed to discuss that on regular email' investigation turned into a massive scandal, wrecking multiple marriages. It turned into a whole lot of meetings with his VERY angry CO. Don't do stupid shit on company email (and REALLY don't do stupid shit on DOD servers)."


6."My best friend was madly in love with a woman and wanted to marry her. They lived together and were very happy. As a birthday gift, she bought him a plane ticket so he could fly out to see me. While he was with me, he would talk to her every so often, and every time he got off the phone with her, he would tell me something just wasn't right. His spidey senses were tingling. He came home and found evidence that she had someone over at their place. She initially denied it, but eventually, she admitted to having a male coworker in the house. Her buying the ticket was just a way for her to have the place to herself for a three-day sex romp. My buddy was devastated and heartbroken. It took him years to recover."


A shirtless man and a woman sit apart on a bed in a dimly lit room, both appearing deep in thought
Delmaine Donson / Getty Images

7."One of my wife’s cousins died of cancer after a 30-year marriage. When her husband was clearing out her home office, he found a box with diaries, receipts, letters, and hotel keys detailing the hundreds of times she cheated on him with random guys throughout their whole marriage. It went as far as going to take their daughters to meetups and gaslighting them about what was happening."


8."When I was a police officer, a coworker found his wife in bed with another police officer from the same district. The wife would tell the lover about her husband's week schedule, and her lover would change his in order to have sex with the wife while the husband was working. The problem was one day, the husband got dismissed three hours early and went back home without texting his wife first (he had some suspicions, but could never imagine it was another police officer). No shots were fired that day."


A person stands in a doorway watching a couple, partially covered by a blanket, engaging intimately on a bed in a softly lit room
Motortion / Getty Images/iStockphoto

9."I know someone who regularly cheated on their out-of-town girlfriend. I guess he was going to cut all that out when she finished her advanced degree program out of state. She moved to his state, and they got an apartment together. While in the shower, his phone is buzzing with messages. She finds the girl’s username sending all these messages and decides to send her a direct message from her own account. The other girl was completely honest with her, and said, 'I know who you are. I hook up with your BF all the time, including last weekend at your new apartment in your bed.'"


10."My ex-boss fucked his wife's niece in the bushes on a hike. Her husband caught them, and they all got divorced. He ended up marrying his ex-wife's niece a few years later. His ex-wife and his current wife are all best friends again — it's weird."


11."My ex-partner let me raise her kid for four years while cheating on me with her kid's father the whole time. I proposed and she said yes. Then, one night after I paid up his month of private nursery fees and put him to bed, she told me to leave or she’d call the police. She'd tell them I had broken into the house and never to contact them again. They’ve bought a house together now and are seemingly doing well, while I still haven’t fully recovered and don’t know my own self-worth."


Man holds a child close to him as they both look away from the camera, standing near a body of water
Rawpixel / Getty Images

12."In my early twenties, there was one guy in my extended friend group — I didn't know him that well. But, he was a friend of a friend of a friend, and we would occasionally find ourselves in the same social gatherings. He had just started dating this girl (she was maybe a few years younger than us — probably about 18 or 19). They were at the very start of their relationship, so I don't know if they were exclusive to each other, but people knew they were dating. A bunch of them went out one night. I didn't go out, but I heard about what happened later on. This friend of mine got extremely drunk, and the girl he was seeing helped him back to his house. His dad was still up and heard them trying to get into the door (mind you, this was the first time the girl had met his dad). The dad helped my friend to his room and then invited the girl in for a chat and to get to know her a bit. The girl ended up fucking the dad that night."


13."I supported my ex for almost our entire relationship (17 years in total, married almost 10) so she could go to college and get her masters. Throughout the time, I had always suspected that she would be gone longer than usual sometimes, or I just didn’t know where she went. I was working a lot to cover everything. She gets her masters and her first job in years and starts immediately having an affair with a guy at work. He drained our accounts and left me with the kids, stating he showed her what 'a real life' could be. This guy was also married and his wife worked with them. It did not end well for them."


Silhouettes of a man and woman standing back to back, looking downward, suggesting conflict or sadness
Kieferpix / Getty Images/iStockphoto

14."I had a married coworker who started having an affair with a customer who was also married. They'd sneak out to make out in the parking lot on his breaks. He texted her nonstop while he was supposed to be working. The whole store knew about it. He would tell us gross details about their sex life, including showing us the deep-ass scratches on his back (or the time he had to take her to the ER because they failed to do 'butt stuff' and ripped her). We all knew they were both married. Finally, they both decided that they were going to break it off with their spouses. He broke up with his wife, but she decided to work things out with her husband. So he went from two ladies to no ladies. This was years ago, and I do not think he's been in another serious relationship since. And on behalf of all women, I am glad."


15."My boyfriend of seven years cheated on me while I was home saying goodbye to my dying dog and visiting my mom in the hospital. I was also in the thick of an accelerated nursing school program, and it was finals week. My car had ALSO just broken down in the drive-through of a Whataburger that same weekend. The girl he cheated with? A very close friend who was getting married in a month. She begged me not to tell her future fiancé (but I told him)."


16.And finally, "My friend’s husband hired a sex worker for $40 when my friend was a few weeks postpartum with their newborn baby. He invited the sex worker over to their house while taking care of their baby and had sex in their bed. My friend found out later because he was missing from the school where they both worked, and she found out he had been arrested or detained or something. He had gone to the police to report that he was being blackmailed."

"The sex worker started blackmailing him, and he went to a loan shark to get $1,000 dollars to 'pay her off.' When she demanded more money, I guess he decided he couldn’t keep paying and tried to report her to the cops and lie about his involvement.

The cops were suspicious and found out he had hired her. He was fired from his job at the school, and it crushed my friend. To add insult to injury, her mother-in-law blamed her, saying that she hadn’t slept with her husband during some of the pregnancy (it was causing her a lot of pain at the end of her pregnancy, and she physically couldn’t).

She’s still with him. I hate his guts so much, and it makes me so furious that she’s still with that gaping asshole."


A man and a woman clink champagne glasses
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Note: Some submissions have been edited for length and/or clarity.