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People Share The Craziest Cheating Stories They've Ever Heard

Updated October 9, 2020 822.4k views30 items

No one is entirely sure why serial cheaters do what they do . Some are physically incapable of monogamy, other cheaters are just so much better at sharing their time and affection than everyone else. Still others just love love too much. However, it's also possible that cheaters flit about just for the wild stories.

Given all of the Reddit stories about outrageous cheaters, it's highly likely those who practice infidelity do so to make a splash. Why else would you buy Valentine's lingerie for your spouse and your person on the side from the same store?

For more crazy stories about cheating, backstabbing, and general betrayal, be sure to also check out The Worst Betrayals People Have Ever Experienced.

  • She Got All Four Of Her Boyfriends To Buy Her A Bag

    From Redditor u/DinosaurFriend:

    I heard this story from a friend who's friends with a girl who has four boyfriends. On her birthday, she requested that all four boyfriends buy her the same purse (neither knew of each other). The boyfriends complied, and she sold three of the purses for money and kept one of them.

    All four boyfriends are extremely pleased when they see her wearing the "purse he got her."

  • She Cheated And Then Dumped Her Husband

    From Redditor u/iam4real:

    My fiancee had an affair.

    I took her back. Found a way to forgive.

    THEN, she broke up with me.

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

  • She Cheated In An Asian Restaurant Right Before Her Wedding

    From Redditor u/Anglicanweasel:

    My boss, an enthusiastic outdoorsman and very gentle fellow, comes to work one day with a black eye and puffy face. I ask him what happened, he explains that there was a fist fight at the AGM of his Hunt.

    Apparently there was a member who had recently split from his wife. They had just married and had had their first child. Unfortunately for their marriage, the child was born Asian. Both husband and wife in this instance were Caucasian. This chap didn't discover this until the child was born, whereupon his wife confessed to committing an act of desperate passion on the floor of an Asian chip shop with one of the staff during her hen night (bachelorette).

    My boss was injured in the fracas that erupted after one of the members of the Hunt decided that four months after the fact was long enough and he could crack a joke about it during his speech to the assembled members of the Hunt.

    He claimed afterwards that George had no sense of humor.

  • He Cheated With His Kid's Godmother

    From Redditor u/OliveTree11:

    I got talking to a woman on public transport randomly, just normal polite chit chat before she turned to me with a grave look and said "my husband had an affair." I apologized because I didn't really know how else to respond. She told me, of the 12 years they had been married he'd been seeing someone else for seven. They had three kids 17, 13, and six.

    The woman he'd been seeing was his best friend, she was a huge part of their lives. Their oldest son's Godmother, she had Sunday lunch with them all almost every week.