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“What’s The Wildest Cheating Story You’ve Witnessed Or Happened To You?” (30 Answers)

“What’s The Wildest Cheating Story You’ve Witnessed Or Happened To You?” (30 Answers)

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Infidelity can be a pretty open-ended term. But whether we're talking about a one-night stand, sexting, flirting, or a secret lunch with a colleague, it basically boils down to sexual or emotional activity outside the agreed-upon boundaries of a relationship.
To better understand the lengths people go to in order to satisfy their desires, Reddit user WCh3L3 made a post on the platform, asking, "What's the wildest cheating story you've witnessed or experienced?" An interesting question, considering that many of us might not recognize the signs of an affair even if we suspect our partner.
Below, you’ll find some of the most memorable comments from the thousands shared in the discussion. Also, don't miss the conversations we had with Dr. Janneke Schokkenbroek and Dr. Talal H. Alsaleem — you'll find them in between the submissions.

#1 The Wildest Cheating Plot

The Wildest Cheating Plot
I knew a guy years ago that was a private investigator. Many times he was approached by a spouse who suspected their partner was cheating.

He had a slam-dunk strategy. He would suggest his client sign up for a course, whether a hobby thing, or educational. The key was that the class would happen for a period of weeks, all on the same day of the week, and all at the same time of day.

Then, while his client was in class, he would follow the spouse.

Caught them every time.
121points

#2 You Won't Believe They Actually Happened

You Won't Believe They Actually Happened
My ex-wife pretended to be admitted to a mental health ward for long term treatment while actually staying with her new man and cheating on me.
80points

To learn more about infidelity, we contacted dr Janneke M. Schokkenbroek, a postdoctoral researcher at Delft University of Technology and Inholland University of Applied Sciences, the Netherlands.

"When it comes to cheating, there are a lot of misconceptions," Schokkenbroek told Bored Panda. The first one is cheating is always about sex. Not true!

"Emotional cheating is just as real and, for many, even more painful. This happens when someone forms a deep emotional connection with someone else, sharing personal thoughts, dreams, and vulnerabilities. It's not always physical, but it can still feel like a betrayal because it undermines the emotional intimacy that’s supposed to be exclusive to the relationship," explained. Schokkenbroek

"What makes emotional cheating so tricky is how easy it is to dismiss. It often starts as and looks like 'just a friendship,' but over time, boundaries blur. If secrecy creeps in, or if your partner starts prioritizing someone else over you emotionally, it might be time for a tough conversation."

#3 When Thanksgiving Gets Awkward

When Thanksgiving Gets Awkward
I know a guy who’s wife was cheating with his cousin (also married), he finds out, and decides to have everyone over for a supper. Half way threw supper he looks his wife dead in the eyes and says, “I know you two are f*****g”, right in front of affair partner and his wife too. S**t blew up and everyone got divorced, affair partners never got together either.
78points

#4 Pizza Delivery And Unexpected Twists

Pizza Delivery And Unexpected Twists
I used to go to a comic shop. And the comic shop owner knew all of the gossip in the area. Nice dude. Remembers all of his regulars and asks about you if he hasn’t seen you in awhile to check in on people. Lot of people in the area grew up with his shop. So he’s got stories.

Anyways he told us about this story from some years back about this regular. Who disappeared for a few months. Comes back one day. And the shop owner asks him, “hey, man. Haven’t seen you in awhile?”
Kind of like where have you been. The regular was like oh I’ve been getting divorced. I had to move it was a whole thing.

So naturally the shop owner asks. “Why are you divorcing your wife?” The regular caught his wife cheating.

He had picked up a 2nd part time job as pizza delivery man because he was trying to fund to take his wife on her dream vacation. All of the money he earned from that job was supposed to go into that vacation. He had been working this job for like 6 months. It was a whole secret. She didn’t know he was doing that for her. Because he was trying to surprise her.

He was the pizza delivery man at the motel. She was cheating at him with. The dude she was cheating on him with answered the door with her right next to him.

He apparently didn’t even go back to the pizza place. He quit on the spot. Went home. Packed his s**t and left town.
77points

Another popular myth, according to Schokkenbroek, is that cheating means you're unhappy in your relationship.

"Sure, being dissatisfied in your relationship can lead to infidelity, but it's not always that simple. Sometimes, people in happy relationships cheat too — maybe because they crave novelty, excitement, or validation," she explained.

"The idea that 'if someone cheats, they don't love their partner' isn't always true. You can genuinely love your partner and still be drawn to someone else, often for entirely different reasons, like a spark of excitement or sexual attraction."

"Of course, this doesn't make it okay," Schokkenbroek added. "Cheating is still a betrayal of trust. It crosses (spoken or unspoken) couples' boundaries and can deeply harm the relationship. Whether it's due to unhappiness or not, infidelity is a wake-up call that something — in the relationship and/or within the person cheating — needs attention."

#5 Libido Was Too High

Libido Was Too High
A guy cheated on me because "my libido was too high."

Yes, you read that right.

*"You wanted sex so much that I needed a break by having more sex to get away from all the sex we were having."*
75points

#6 Cheating Confession That Left Everyone Speechless

Cheating Confession That Left Everyone Speechless
I’ve shared this in the past, but it’s worth repeating

We were deployed overseas and my buddy got the dreaded “dear John” letter from his fiancé. She included a photo of another man’s d**k in her mouth to twist the knife a bit. He proceeded to have said photo made into Christmas cards for her whole family. About six weeks go by and the letters and phone calls to the command com in. He goes before the command, and explains the situation and shares the letter and picture with the higher ups. They were pissed, but there was no punishment for him.
71points

One more stereotype that Schokkenbroek would like to disappear is the notion that 'the other woman' is the villain and the homewrecker.

"Not only does this phrase unfairly paint the secondary partner as the villain, but it also shifts focus away from the cheater's responsibility," she said. "Plus, calling them 'the other woman' is outdated and gendered — secondary partners can be men, non-binary people, anyone."

"In reality, these situations are rarely black and white. Sometimes the secondary partner doesn't even know they're someone's secondary, or they genuinely fall for the cheater and find themselves in a very painful and complex situation, which often comes with a lot of heartbreak for them too. Instead of vilifying them, let’s use neutral terms like 'secondary partner' that better reflect the nuances involved."

#7 Ambulance Called For The Ultimate Betrayal Fail

Ambulance Called For The Ultimate Betrayal Fail
A friend of a friend found out that her husband was cheating when she got to the hospital to see her husband who had just moments before been brought in by ambulance after a serious car accident only to be denied entry to his room because “his wife was already in the room with him”.

He had two simultaneous lives with two women, neither of which was aware of the other.
59points

#8 Grandpa Ended Up In The Hospital

Grandpa Ended Up In The Hospital
My friend's mom was in a relationship with a guy for years and they ended up getting engaged and due to marry.

The guy was a senior director of a company for which he travelled every week abroad for business.

Eventually, the guy had a heart attack and when my friends mom turned up at the hospital, his wife and 2 kids were there also.

Turned out he was already married with children and living a double life the whole time. When he went 'abroad' for business, he was simply going back to his actual family
55points

#9 The Bouquet That Broke The Deal

The Bouquet That Broke The Deal
I was a florist. A guy came in and ordered flowers for 2 different women, his girlfriend and his wife. He puts both orders on the same credit card, one he shares with his wife. Everyone in the shop volunteered to deliver them to see what these women looked like. Later that day the wife calls to ask who the second order was sent to. Since her name is on the card we feel no obligation to secrecy so we told her. Florists in general are pretty good at keeping secrets but in this case she paid for the flowers. I've also disclosed anonymous sources if a woman has received flowers from an anonymous source. I don't want to be involved in a stalking scenario.
53points

A 2022 survey found that one-third (33%) of Americans admit to cheating cheated — either physically, emotionally, or both.

However, only 57% of cheaters were caught, meaning 43% have managed to keep their infidelity a secret.

In most cases (71%), Americans who cheated did not want their partners to find out about it.

#10 Story Is So Crazy Even She Can’t Believe It

Story Is So Crazy Even She Can’t Believe It
In a small town the husband kept telling people he had an open marriage; finally someone asked his wife about it, she was unaware of this new arrangement.
50points

#11 Caught Running From Cheating Scandals?

Caught Running From Cheating Scandals?
Had a coworker who cheated on her live-in boyfriend. She would tell him she was going for a run, put on her shorts without underwear and would f**k her side piece in the apartment parking lot. So then she would come back inside sweaty 30 mins later and needed to shower and it all made sense to her boyfriend, he never questioned it. She was an awful human.
50points

#12 When You Catch Your Partner Cheating

When You Catch Your Partner Cheating
I dont cheat.

BUT my mom is a serial married man dater

She has slept with

1. First boss, the mayor of the town she grew up in
2. My father, who was married to his first cousin and had a daughter by. she got knocked up with my older full sister and the eloped and he then became a bigamist and had to divorce his first wife. My older half sister hated me till she died in 2020.
3. Her divorce lawyer when she divorced my father 10 yrs later
4. Our family therapist who we went to to deal with the divorce. Suddenly we stopped seeing him and I never knew why. I saw him once at my Uncles restaurant and said Hi, and he turned white and ran out. Leaving me thinking I was somehow the cause of not seeing him anymore
5. My moms CEO Boss when she got a job after the divorce, she used to dye his eyebrows and hair at the office and give him foot massages and yet thought we were all dumb. I went no contact with her in 2003 because she hung up on me to be with him when I was having a personal crises
6. The mailman, when she was on a break from CEO Bossman. His wife came to our house to confront my mom. I then started ordering As Seen On Tv s**t C.O.D. and he didnt wanna knock on the door so hed just pay for everything himself.

The reason I said all this is cause I hate when women say, "He didnt make those vows to me..." as if being a skank is okay just because he didnt make the vows to you.

It is not OKAY. It does a lot of damage.

I never cheated on any one of my BFs...
49points

Schokkenbroek believes that no single action screams, "Oh no, my partner's cheating!" but there are some things that can stand out:

  1. They've gotten secretive. "Maybe they’re guarding their phone more, changing their passwords, or overall appearing more protective of their privacy."
  2. There's emotional distance. "If they seem more disconnected, irritable, or overly critical, they might be emotionally investing elsewhere."
  3. Unexplained time away. "Late nights, vague excuses, or 'busy' weekends could be a sign.
  4. A new focus on appearance. "If they’re more often hitting the gym or dressing up without a clear reason, it might raise an eyebrow."
  5. "Changes in sexual behavior. "Whether their interest spikes or drops, it’s worth paying attention."
  6. And, of course, 'souvenirs,' like unexplained bills, or unfamiliar items and smells...

"That said, please note that a list of 'red flags' suggests that these things are instantly noticeable, but such relationship dynamics often shift slowly and naturally over time," Schokkenbroek highlighted. "Changes in behavior often warrant a conversation rather than immediate suspicion. Open communication is always the first step before jumping to conclusions."

#13 Caught In The Act!

Caught In The Act!
Bunch of men in a small town lied to their wives about hunting trips and were f*****g each other in a motel
Report
47points

#14 Couples Caught Red-Handed

Couples Caught Red-Handed
Just got home from deployment, on an anniversary trip with my (now ex) wife to Vegas. We go to a couple cirque shows, do some paigow, get a very fancy dinner, the whole anniversary spared no expense experience.

She was passed out drunk and her phone was blowing the f**k up with like 20 messages from an unsaved number. So I looked. They were very romantic and sexual messages and pictures. She had been texting him the whole night. Even while we were at dinner she told him she wished he was there instead of me. She had been messaging him for months, my whole deployment basically.

Well I dug deeper, started reading other message chains. I found like 9 other affairs with both men and women, she was even a third in a throuple and caused the husband and wife to get divorced because she kept breaking the rules and f*****g the husband without the wife there/behind her back.
47points

#15 Couple Caught In A Cheating Tango

Couple Caught In A Cheating Tango
My dad cheated on my mom with a coworker. She suspected him of an affair but didn’t know for sure until he didn’t come home one night. I remember walking in the kitchen the next morning and asking my mom where he was, I was only 10-11 years old btw, and she goes “he didn’t come home last night.”

So she called him at work and he said he slept at a friends bc he had too much to drink. My mom called the friends wife, she confirmed my dad was not there at all, and that’s all my mom needed to know. It destroyed our family, my mom packed his s**t and left it by the door. She got addicted to prescription pills afterwards and tried to k*ll herself. She only lived bc I found her and called 911. After that she just left, took off, dumped me and my sister with my dad who will ill-equipped to raise two almost teenagers. So he met this super b***h who was recently widowed, they got engaged, and before I knew it I was living with her and I had six stepbrothers and sisters. Things only got worse from there. I enlisted to get away from it all. Whole thing f****d me and my sister up pretty bad
43points

#16 Wedding Kiss Turned Into The Wildest Cheating Story

Wedding Kiss Turned Into The Wildest Cheating Story
My Ex wife missed our last dance at our wedding reception because she was f*****g her cousins in the bridesmaids change room.
42points

#17 Caught In The Act

Caught In The Act
High school sweetheart and I went off to college, different schools, while I was visiting I was walking around the house to the front door. Window was open and I overhear her talking to another high school guy friend of mine that is in college with her about how she doesn’t know how to tell me she cheated. He caught her with a friend of his and was forcing her to fess up before he did. So that broke us up needless to say.

She begged me to forgive her. About 3 months later I relented and had her visit me at my college. We went out that night. Food, drinks, and finally a house party. Before we were about to leave I went up to a friends room to grab a bag of weed from him. 15 minutes later I come down, go out to the porch, look to the left, and there she is making out with some random guy we hadn’t even met before. She literally met him 2 minutes after I went upstairs.

She cried all night. I was crying laughing that she had so little self control. I ended up having her sleep on the couch and she went home before I woke up. Haven’t spoken since. That was about 20 years ago.
40points

#18 The Most Bizarre Cheating

The Most Bizarre Cheating
A family friend's husband was having an affair for 20+ years and that woman knew the entire time about his family. He was at her ranch one time and was bucked off a horse and broke his back. The affair partner called his wife to tell her and acted like everything about this situation was normal and the wife had no reason to act all upset at the affair. Some people really just have no shame.

Guy lived and made a complete recovery, left his mistress and they stayed together since they were working on their relationship. He died a few years ago and the wife finds out he never actually left his mistress just lied.
38points

#19 She Caught Him Cheating

She Caught Him Cheating
My best friends dad invited his coworker/mistress to his home and let his unknowing wife cook for her and all. Wife eventually finds out and he throws her out, divorced her, and marries the mistress. He was a pastor.
37points

#20 When Mom Knows About Your Cheating Drama

When Mom Knows About Your Cheating Drama
When I worked a college, this guy cheated on his girlfriend.... with her mother! He dated both of them, knowing they were related, but they didn't know they were dating the same guy.

He got both of them pregnant too, and vanished shortly after they found out he dating both of them. We used to semi-jokingly wonder if he ran away or was stuffed into a barrel at the bottom of the lake.
34points
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