People Share The Craziest Cheating Stories

From Redditor u/Mnbvcxzlkjhgg:

My sister works in a lingerie boutique. A man came in for Valentine's Day and bought two beautiful outfits. He asked for them packed separately with two Valentine cards: one for his wife and one for his mistress.

At first, my sister thought he joked. The outfits were not the same size.

From Redditor u/haibane_rakka:

Someone I know is getting a divorce. Her husband is having an affair with his much-younger cousin. The age difference is not a big deal legally in their area, but the whole situation is messed up.

From Redditor u/rabidjade:

A former coworker found out his wife filmed adult entertainment and earned almost nothing after years of marriage. He found one of her DVDs hidden in the house. He thought it was a birthday gift and watched it when she was gone.

When he confronted her, she just replied she did it for him. He broke down and needed therapy for a few months after the divorce was final.

From Redditor u/is_not_chicago:

My girlfriend of five-and-a-half years cheated on me while I slept in the next room in our bed. I found out the next day.

I remember her coming in to kiss me sometime that night. I never asked if it was before or after.

From Redditor u/DinosaurFriend:

A friend of a girl with four boyfriends told me this story. On her birthday, she asked all four boyfriends to buy her the same purse. They agreed. She sold three purses for cash and kept one.

All four boyfriends were very happy seeing her wear the "purse he got her."

From Redditor u/iam4real:

My fiancee had an affair.

I took her back. I found a way to forgive.

Then, she broke up with me.

"You didn't get mad enough," she explained.

From Redditor u/Anglicanweasel:

My boss, an enthusiastic outdoorsman and gentle man, arrived at work one day with a black eye and puffy face. I asked what happened. He explained a fistfight happened at his Hunt's AGM.

A member recently split from his wife. They had just married and had their first child. The child turned out to be Asian. The husband and wife were both Caucasian. He did not find out until the child was born. Then, his wife confessed to an act of desperate passion on the floor of an Asian chip shop with a staff member during her bachelorette party.

My boss got hurt in the fight after a member of the Hunt decided four months was long enough. He could make a joke about it during his speech to the Hunt members.

He later claimed George lacked a sense of humor.

From Redditor u/OliveTree11:

A woman on public transport started talking to me. She turned to me with a serious look and said, "My husband had an affair." I apologized; I did not know how else to answer. She shared that in their twelve years of marriage, he had been seeing someone else for seven. They have three children: 17, 13, and six.

The woman he saw was his best friend. She was a huge part of their lives. She hosted Sunday lunch with them almost every week; she was the oldest son's Godmother.

From Redditor u/CPTNBob46:

When my dad was twenty, his mother (mum-mum) had a feeling that my grandpop was cheating on her. She is the kindest woman; she did not feel it was right to spy on him to find out. Luckily, my mom's mother (Nanny) allowed spying. Nanny tracked him sometimes and found he met a woman in the park every few days and got into her car.

Nanny took my Mum-Mum to the park to show her. They watched my grandpop get out of his car, into the strangers, and then it happened. They walked to the car and found him eating cake. He got angry they followed him; they had a big fight. He also slept with this lady, but she cooked meals for him. That is why they met in the park; she brought him food, he ate, then went home.

They divorced. Years later, after I was born, my mom found my dad sleeping with her brother's wife (my aunt by marriage). This happened only a few months after my uncle died. His excuse was she cooked for him, and my mom never wanted to. Now, that former aunt is my step-mom, my cousins are my siblings, and explaining it is hard.

From Redditor u/Xenophorge:

I knew a girl who took the prize home. She married my buddy right after high school graduation. He joined the military and went for training. She started messing around with another guy. Then, she broke up with that guy to start messing around with his older brother.

My buddy is still training here and making money while she spends it fast. She stopped messing around with the older brother and went to their father! Now she is with the father. He convinced her to become a dancer at the bar he worked at, and she got on stage for everyone to see. Some nights, he brought her and other girls home for good times, all while married to my buddy, who left her...

From Redditor u/craftyzombie:

A guy I knew in high school did this. He married a girl for several years. She needed a kidney transplant. He matched and gave her one of his kidneys instead of waiting in line. Three months after the surgery, she cheated on him and divorced him.

From Redditor u/flithymick:

An old friend's wife cheated on him many times. One day, she claimed she was leaving for another man. The truth emerged: she left because he only wanted her for good times and wanted nothing more. She returned to the friend. She made him apologize so she could reconcile. He did, and they remain together. I do not know if she still cheats; I no longer speak to them.

From Redditor u/bloodthirstyllama:

My old housemate was engaged to a guy and bought a house with him. On Christmas Day, after eight years together, he told her he did not love her, hadn't for six months, and slept with his secretary. She broke down. He got angry, told her to sleep on the couch, and then told her to move out the next day.

Two months later, he officially started with another girl. He took her to New York, the place planned for my housemate's honeymoon.

From Redditor u/ELTepes:

A friend and I worked together at a gas station one day. Neither of us was good at customer service, but we were in good moods. A woman came in, and my friend asked how her day was. That was a mistake.

She told us she got engaged that morning, and we both congratulated her. The story did not end there. She said her boss let her go home early to celebrate. She came home and found her fiancé making love with her mother.

I could only think, "So, the wedding is off?"

From Redditor u/married_a:

A friend of my wife dated this man. The friend became pregnant and had the baby. Complications arose during delivery, requiring a C-section. The man refused to gown up for the delivery room. He needed to move across the hall to his other girlfriend who was also in labor. The man had two girls pregnant and in labor at the same time. Later, he harmed my wife's friend.

From Redditor u/Mighty_moon_worm:

I will share my story. I saw this girl for four months, and she started boring me. I decided to flirt with a few guys and have fun, but I never acted on it. I talked to one guy for a day and a half; he asked me out. I said no, but maybe someday. I lied, saying I was not ready for a relationship.

He FaceTimed me while I was with my girlfriend and looked at her once before hanging up. She called him right after and started yelling at him. We were cheating on each other with the same guy.

From Redditor u/BlackCaaaaat:

What happened to my cousin: she let someone get with her boyfriend. That was bad enough. The other woman was her mother (my Aunt). After that, my cousin went off the deep end and became a... [user]. She is okay now, though, considering.

From Redditor u/DamWrights:

During a camping trip with my new fiancé and friends, I felt sick and went to bed early in our tent. I woke up to my guy and best friend of fifteen years hooking up right next to me. He broke my heart, so I broke his nose.

From Redditor u/Jesus_Faction:

A friend dated this guy for seven years before they married. They split after one month because she found he cheated with her maid of honor. The maid of honor tried to get him to pay alimony.

From Redditor u/Saracantstop:

A friend recently married, sharing how her wedding brought family together after a rocky time. Her mother got cancer at 34. She lived ten more years, passing at 44. While this happened, my friend checked the family computer and saw her father's last session message open. He talked to her mom's best friend. They said things like, "How much longer till she's gone and we can finally be together?" and "I can't wait till you can finally be mine."

She and her brother confronted their father, who felt bad but kept seeing her mom's best friend. Her mother passed away not knowing what happened between them. She and her brother cut off contact with their father for seven years after it happened. He still dates her mom's best friend, and they "always say they still feel incredibly guilty about what they've done." This guilt stops them from marrying.

It took my friend years to forgive them and let them back into her life. This is a sad story about a family ruined by cheating.

From Redditor u/fingeredbykreuger:

My ex-boyfriend said he had to work on our anniversary, which was the night before my birthday. I felt let down, but I accepted it. The next day, he told me his kidneys were acting up—he has a bad kidney problem that gets worse when he drinks—so he could not come to my birthday dinner.

He showed up drinking and hooking up with one of my best friends on our anniversary.

From Redditor u/sadeqsr:

My ex and I dated for two and a half years. I came home from a business trip without telling her so I could surprise her. I walked into my apartment and saw her banging my younger brother on the kitchen counter. I was devastated; my brother did not apologize. I just took my things and left.

I still hurt thinking about that situation while I write this.

From Redditor u/lewismacp2013:

My brother's friend talked to another girl on a dating website for months. Finally, his girlfriend asked him if he was talking to another girl. He said no. She confessed she was the girl from the website.

From a former Redditor:

My old roommate's mom cheated on her husband. They shared forty years. She had sex with another man in her daughter's bed while the whole family was at a party downstairs. No one discovered it, but it was really bad of her. I was the man she cheated with.

From Redditor u/insipid-rainbow:

A guy cheats on his pregnant fiancée who has an older child with him.

He cheats with two women.

The two women are a mother and daughter.

His fiancée learned the truth at 38 weeks pregnant.

He then cheated on her again with his boss's pregnant, married daughter.

They split; she took the house.

From Redditor u/heyrubyway:

A high school friend of mine was a really hot, tall blonde girl who made guys go wild. She liked getting attention and I think she especially liked flirting with guys who had girlfriends. She seemed to not care about other people’s feelings.

The worst part was she started an affair with her high school math teacher during our last year of school. She was nineteen; he was around thirty-five. He had just married his wife who was pregnant then. The woman and the teacher exchanged emails for months. They met up the first time on the night his wife gave birth to their son. He stayed with his wife and son in the hospital until the evening, then left for one of his students. This makes me feel sick about how someone could do that to their partner.

The wife found out eventually. They are still together now, seven years later, after a short break.

From Redditor u/slyn69:

A girl I know visited her family in Chile without her boyfriend. While there, she cheated on him and got pregnant. She flew back home to her boyfriend, manipulated him into unprotected sex (so she could trick him into thinking he got her pregnant), then she got the abortion. Her boyfriend blames himself and gives her all this emotional support. They are now happily married.

To this day, she probably thinks she is a good person for not having the baby and making her husband raise a kid that wasn't his.

From Redditor u/B0TTiG:

I work at a call center for an online travel company. This morning, the first call came from a woman claiming a fraudulent charge on her account from our company. She gave me the credit card number, and I pulled up two round-trip tickets bought a week ago. They were going to a casino for the weekend, and this was the first her wife had heard of it.

She said he denied making the purchase and had no idea what it could be for. Once she saw what was happening, she blurted out a name that matched the name on the ticket. There was some history because she identified who he was taking on the trip without me saying anything.

He posted a trip review in our system, saying he hadn't gone yet but was ready to celebrate his new love's birthday at the casino. The woman on the phone became angry and tried to remain polite while the call ended.

Redditor u/HeroOfTime1987:

I worked in a local video store during high school. About once a month, an attractive blonde woman came in with a man on her arm. They rented adult videos and left quickly. Since this was the only store nearby, locals frequented us. I knew this man as the father of a kid from my class.

One day, a woman rented a video. She gave me her card; I scanned it and saw a late charge. She asked the movie title so she could decide if her son or daughter should pay the fee later. I looked up the title and turned the screen toward her to avoid saying it aloud. She turned red and asked if her children could have rented it. I checked the account info, saw the last name, and felt as red as her. I told her I knew her kids were underage, so we would not rent this video to them. She asked for a rental history printout, and I gave it to her even though it was against policy.

I felt bad seeing that kid depressed a week or so later.

Redditor u/kukukele:

A friend worked at a golf course. During an outing, a woman showed up wanting to surprise her husband and meet him on the course. My buddy found the hole he started on, hopped in a cart, and drove the woman out there.

Instead of taking the long cart path, he took a shortcut through an area maintenance staff uses. During the shortcut, they saw a cart in the woods with the husband getting a BJ from his secretary.