The 10 Worst People To Cheat On Your Girlfriend With

Men are dumb. Men believe they can sleep with someone who is not their girlfriend and get away with it. Men also believe that they can sleep with someone who is not their girlfriend, but who their girlfriend knows, and think they can get away with it. Men also believe that they can sleep with someone who their girlfriend knows, get away with it, and expect to stay with her. This is proof that, of course, men are dumb.

But there are varying degrees of dumb. For some men, they may legitimately find a woman that they like while they are with someone, decide to date her, and in the process break up with their current girlfriend. Then there are men who sleep with any of the 10 women on this list. To cheat with these girls is lazier than the writers of Adam Sandler's last five movies.


10 Her Sister

How your girlfriend views her:

Her sister is one of her earliest confidants. She’s someone who knows all of her secrets. They share parents for crying out loud. The bond with this girl is unbreakable because this relationship is as old school as it gets.

Why she’s the worst to cheat with:

Remember how skeptical her dad was during the first meeting? How he was probably thinking, “This guy is having sex with my daughter? At least my other one is safe from him.” Now picture running into him at the grocery store, at the mall, or at a baseball game. The best case scenario on how that would end would be a Sister Wives spinoff.

Celebrity cautionary tale: Larry King

Larry King’s wife accused him of sleeping with her sister, Shannon Engemann, back in 2010. She threatened him with a divorce and it reached a boiling point when she went all Rhonda Rousey on him in Beverly Hills that same year. This is based on allegations that he bought Shannon luxury gifts, including a $160,000 car. This goes to show that even 200-year-old men may never recover from this.

9 Her Best Friend


How your girlfriend views her:

Please bear in mind that her sister and her best friend can be the same person. If they are different people, then surviving the impending nuclear attack is more likely.

Why she’s the worst to cheat with:

Think about having a Bengal tiger as a pet. With regular care and feeding, there’s a good chance that the tiger won’t go all scratchy-scratchy against its owner. By keeping its killer instinct at bay, the tiger knows it can keep eating and won’t end up as a sweet rug on the owner’s cabin floor.

Relationships among female friends are the same. Both women know things can get ugly real fast when men are involved. A girl can forgive her sister if she sleeps with her boyfriend. Her best friend? Well, just know that every conversation she has with anybody about her ex-boyfriend and ex-best friend will start with a personal insult and, if she’s really mad, end with a racial slur, just for good measure.

Celebrity cautionary tale: Shania Twain

Shania’s husband and best friend both burned her. It’s understandable Shania didn’t like being done dirty like that, so she took it to the next level. Shania wrote about this sordid affair in her tell-all book and she even married her former best friend’s ex-husband, too. Aren’t Canadians supposed to be nice? She’s practically a war criminal up there all because of her ex-beau.

8 Your Co-worker

How your girlfriend views her:

She doesn’t trust female co-workers. The reasons are simple. Imagine sending a girl into a place where men can stare at her all day, make up inane excuses to see her, compliment her, go out for drinks after work, stay late in the office, and spend countless hours talking. Now flip the script and imagine it’s a stupid, stupid man and there are women doing these same things. That’s why she doesn’t trust her.

Why she’s the worst:

Think about the worst night of sex ever. The humiliation. The embarrassment. The prayers that the video was destroyed. Now think about how everyone she knows, including your girlfriend, will eventually find out.

Celebrity cautionary tale: Brad Pitt and Angelina Jolie

This one was obvious. Ten years after leaving Jennifer Aniston for Jolie, Brad Pitt wakes up every morning and realizes that he is supporting six little ankle biters. Rumors suggest Brad has actually not stopped crying since 2005.

7 A Stripper


How your girlfriend views her:

She’s relatively harmless. Most women know that strippers are just a fantasy for men. Plus, a girlfriend knows that men with a neck the size of a Christmas ham will fold a patron in half if he tries to touch one of the girls. But the problem is that girlfriends know that the stripper’s whole purpose is to get her boyfriend to believe she wants to have sex. The threat is just always there.

Why she’s the worst:

It’s expensive. In 99.99% of the cases, strippers want money if they’re going to sleep with someone. Just think about it. If it costs at least $20 for a lap dance, imagine what actually sleeping with her will cost. For men with slush funds their girlfriend is unaware of, they can pull it off. For the majority, explaining why the bank account is negative $3,000 is difficult to explain.

Celebrity cautionary tale: Josh Duggar

Strippers aren’t exactly shy. Just ask Josh Duggar. Duggar paid Danica Dillon $1,500 for a night of sex one evening, but the worst part is that he stiffed her (no pun intended) $500 bucks afterward. The fallout was so bad that the only way Duggar gets out of this is if he goes all Nicolas Cage in Face/Off and just gets some other dude’s face right on his.

6 An Escort

How your girlfriend views her:

She probably thinks her boyfriend is too broke or too cheap to afford an escort. But women know the score. Just like there are guys who can afford a brand new BMW, there are just as many guys who will pay for an old Ford Escort (or an escort named Ford). As long as he’s willing to part with the money, some other woman will be there to take it.

Why she’s the worst:

It’s illegal. It’s, so, so, illegal. Sleeping with her sister, her best friend, or with a stripper won’t land someone in jail. Getting caught with a stripper not only means total humiliation in front of friends and family, but it’s also not even something cool to go to jail for. There are guys locked up that held up liquor stores, dealt drugs, or were gang leaders. They use guys who are in the slammer because they paid for hookers as a mop in the kitchen. It’s just not worth it.

Celebrity cautionary tale: Tiger Woods

This past May, reports surfaced that Tiger spent $40,000 paying for sex. This information not only made it through the gossip mill, it also led to the end of his relationship with Lindsey Vonn. It begs the question though: what does $40,000 actually get Tiger? Is it like at a hotel where he gets breakfast in the morning and a back rub? Can he use a coupon? Either way, Tiger’s game and life are circling the drain because of his inability to stay away from these girls.

5 A Random One Night Stand


What your girlfriend thinks of her:

She’s a nameless, faceless threat to the relationship. She’s the girl who just broke up with her own boyfriend, who hasn’t gotten laid in a long time, who’s too drunk, or some visitor from out of town looking for a good time. She’s also the girl that doesn’t care that her boyfriend has a hairy back or breathes through his mouth. She’s like the IED of relationship enders. Totally unexpected, but totally killer.

Why she’s the worst:

Because it’s not real. She’s not a friend. She’s not an ex. She’s probably not famous. She’s not a co-worker. She probably even gave out a fake name and number. She’s the equivalent of a spam email and cheating with her is like thinking, “Cambodian princess needs our checking account number? Sounds legit.” It’s just irresponsible.

Celebrity cautionary tale: Josh Duhamel

Fergie’s hubby should have just gone to a Waffle House when he was in Atlanta instead of hooking up with a one-night stand there. The headline, “Movie Star Eats At Local Restaurant” where there is a picture of him giving a thumbs up to a waiter is a far cry from, “Josh Duhamel Bangs Atlanta Local” where the media finds a photo that perfectly frames that To Catch a Predator frown on him. Bad move, Josh.

4 Her Mom

What your girlfriend thinks of her:

In the hit show Jane the Virgin, one of the underlying themes is the mother-daughter relationship between the main character and her mom. Part of the reason for the show’s early success is because it reveals the complex and critical relationship between a girl and her mama. They expect each other to share everything - except boyfriends

Why it’s a bad idea:

This isn’t 1850 Kentucky, that’s why.

Celebrity cautionary tale: Lamar Odom (maybe)

(At the time of this article, Lamar Odom is in critical condition in a Las Vegas hospital and we all hope for his speedy recovery)

Lamar brought Kentucky with him to California if rumors that he slept with 59-year-old Kris Jenner are true. Just think about the baby those two would have. It would probably look like that creature from Up where it’s 11-feet tall and drives everyone crazy. Real smooth Lamar. At least he didn’t get it on with Caitlin.


3 Your Ex-girlfriend


What your girlfriend thinks of her:

The ex-girlfriend is like an old Blackberry cell phone. It was difficult, unreliable, and lacked a touch screen interface that made it hard to access the wireless network... Maybe that last one doesn’t make sense, but the other two do. Regardless, like a Blackberry, it’s no good for the long term, but when her boyfriend’s iPhone breaks, he’s reaching for old faithful.

Why she’s the worst:

There’s this episode of Futurama where the main character, Fry, is addicted to a soft drink called Slurm, despite the fact that it is made from the green, sticky slime of a gigantic worm. An ex-girlfriend is the giant worm. Cheating with her is the Slurm. Even if all is forgiven, expect a TSA-level cavity search after every night out from then on.

Celebrity cautionary tale: Scott Disick

Back in July, Scott reportedly cozied up to his ex-girlfriend, Chloe Bartoli, in Monaco while Kourtney Kardashian was back home nursing a cold with their three kids. He was drunk and touchy-feely all over Chloe, having slipped back into some bad behavior. It’s so bad, Scott’s decision making caused the same face people would make if they saw a monkey driving a tractor. It’s kind of like, “Well, it’s not exactly un-believable.”

2 Your Childhood Friend

What she thinks of her:

A girlfriend looks at her boyfriend’s childhood friends like she does his gas grill. It’s relatively mild, but if she’s not careful, it’s going to blow the place sky high.

Why she’s the worst:

She’s already seen the naked pictures... from 20 years ago. She already knows mom’s favorite place to eat. She already knows everything. She’s like the New England Patriots of relationships. It’s like quicksand. Too easy to get in, impossible to get out.

Celebrity cautionary tale: Arnold Schwarzenegger

There are too many tales to count, but Ah-nold is the strongest warning. Apparently freaked out because Maria Shriver wears her skeleton on the outside, The Schwarz (that’s not his nickname) knocked up his housekeeper and friend of 20 years. Maria knew something was up when the newborn made a Facebook post about how it was legs day at Gold’s Gym.

1 With... Yourself


What she thinks of you:

That’s up to her. After considering all of her choices, the direction of her life, her own personality, and the likelihood of relationship success, chances are, it’s “meh.”

Why you’re the worst:

Because the Internet has not yet developed an “automatic erase” for the browser history. Also, just remember, she’s the only one who doesn’t care how much you slobber when you eat, how fat you’ve become lately, or that she could probably beat you up. She still chooses to be with you. By spanking your own monkey too often, it will leave her feeling neglected and she will move on to someone who sucks less.

Celebrity cautionary tale: Take Your Pick

Celebrities are people too so there is no telling how many stories exist where a girl caught her guy watching what she can assume is only legal in Germany.



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