Random Craziest Cheating Stories People Have Ever Heard (30 items)

• (#20) His Wife Was Dealing With Cancer, And He Cheated With Her BFF

  From Redditor u/Saracantstop:

  A friend recently got married and told me about how her wedding brought her family together, but it had been a rocky road. Her mother was diagnosed with cancer at the age of 34. She lived another 10 years and [passed] at the age of 44. During this time, my friend is on the family computer and notices her father's instant message window from his last session is still open. He's talking to her mom's best friend. They're saying things to each other 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 confront her father, who is remorseful, but does not stop seeing her mom's best friend. Her mother [passed] never knowing what was going on between them. She and her brother cut off contact with their father for the last seven years since it happened. He's still dating her mom's best friend and they "always say they still feel incredibly guilty about what they've done." It's the reason they won't get married.

  It's taken my friend years to forgive them and let them back into her life. Very sad story about a family ruined by infidelity.
• (#22) She Cheated On The Kitchen Counter With Her Boyfriend's Little Brother

  From Redditor u/sadeqsr:

  My ex and I were dating for two-and-a-half years. I came back from a business trip without telling her when I was coming home so I could surprise her, I walked into my apartment saw her [banging] my younger brother on the kitchen counter.... I was devastated, my...brother didn't apologize or anything. I just grabbed my stuff and walked right out.

  Still hurts thinking about the situation as I'm writing this.
• (#26) He Cheated With His Student Right After His Wife Gave Birth

  From Redditor u/heyrubyway:

  A high school friend of mine was that kind of really hot tall blonde girl that made all guys [go wild]. She loved getting attention and I think she especially loved flirting with guys that were out of bounds, like she seduced several guys who had girlfriends. I guess she just didn't really care about other people’s feelings.

  But the worst was that she started an affair with her high school math teacher in our last year of school (she was 19, he was about mid-30s). He had just married his wife who was pregnant at the time. Girl and teacher wrote emails back-and-forth for months. The first time they met up.... with each other was the night that his wife gave birth to their son. So he stayed with his wife and son in the hospital until the evening, then left to go home [to] one of his students... Still makes me stick to my stomach how someone could ever do that to their partner.

  The wife found out eventually, but after a little break they’re still together now, seven years later.
• (#23) He Didn't Know His Girlfriend Was Setting Him Up

  From Redditor u/lewismacp2013: 

  My brother's friend had been talking to another girl in a dating website for months. Finally his girlfriend asked him if he was talking to another girl. He said no. She confessed that she was girl from the website.
• (#13) He Took His Lover On The Honeymoon He Bought For His Wife

  From Redditor u/bloodthirstyllama: 

  My old housemate was engaged to a guy and had just taken out a mortgage on a house together. On Christmas Day, after eight years of being together, he told her that he didn't love her, hadn't for six months, and was sleeping with his secretary. She breaks down, he gets [mad] at her and tells her to sleep on the coach and then tells her to move out the day after.

  Two months later he is officially with this other girl and takes her to New York, the planned destination for my housemate's honeymoon.
• (#27) She Cheated, Got Pregnant, And Told Her Boyfriend The Baby Was His

  From Redditor u/slyn69: 

  A girl I know went to visit her family in Chile without her BF. While she was there she cheated on him and got pregnant. She flew back home to her BF, manipulated him into [banging] her unprotected (so she could trick him into thinking he got her pregnant) then she got the abortion. And her BF thinks it's his fault and gives her all this emotional support. They are now happily married.

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

New Random Displays    Display All By Ranking