Board games are supposed to be fun. At least, that's what the box says before you open it and someone ends up crying over a plastic hotel in Monopoly. But there is a specific, weirdly common phenomenon that happens in living rooms across the country: mom and son cheating. It’s not usually about malice. Most of the time, it’s about a bizarre mix of competitive fire and "house rules" that have spiraled out of control.
You’ve probably seen it. Maybe you were the one doing it.
The kid slides an extra $50 from the bank when Mom isn't looking. Or, more often, Mom sees him do it and just... lets it happen. Why? Because sometimes keeping the peace is more important than the official rules written on the inside of the box lid. But when both parties start bending the reality of the game, the "cheating" becomes a strange sort of dance. It’s a subculture of tabletop gaming that sociologists and family therapists actually find pretty fascinating.
The psychology behind mom and son cheating in games
We have to look at the power dynamic. In most parts of life, the parent has all the control. They decide what’s for dinner, when lights go out, and whether that C-minus in math warrants a weekend grounding. The game board is the one place where a son can feel like an equal—or even a superior.
Dr. Richard Weissbourd, a psychologist at Harvard, has spent a lot of time looking at how parents navigate their children's moral development. He’s noted that parents often feel a pull between teaching "fair play" and wanting their child to feel successful. When it comes to mom and son cheating, the mother might "cheat" in favor of the son to boost his confidence. It’s a protective instinct. She sees him struggling, sees the frustration building, and suddenly a card is "accidentally" drawn from the bottom of the deck to help him out.
But then there's the other side. The competitive son.
Boys, especially in middle childhood and adolescence, often view games as high-stakes arenas for status. If he feels he can't win honestly, the temptation to palm a die or skip a space becomes overwhelming. It’s not just about winning the game; it’s about winning against her. It’s a way of asserting independence. Honestly, it’s kinda hilarious how serious a game of Uno can get when there’s a teenager involved who refuses to lose.
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How "House Rules" blur the line
Is it really cheating if everyone agrees to it? This is where things get murky.
Most families don't play by the literal rules. Take Monopoly. Almost nobody plays the "Auction" rule where if you don't buy a property you land on, it goes up for bid. And the "Free Parking" jackpot? Total myth. It’s not in the rulebook. By the strict definition, almost every family is "cheating."
When we talk about mom and son cheating, we're often talking about the incremental creep of these unofficial rules. Maybe Mom lets him "re-roll" because the die hit a glass. Then she lets him re-roll because he didn't like the number. Suddenly, the integrity of the game is gone, replaced by a shared agreement that the rules are merely suggestions. This creates a "gray zone." In this zone, the son learns that rules are flexible based on who you're with. That's a slippery slope, but in the context of a Tuesday night in the kitchen, it feels harmless.
When the "Cheating" becomes a conflict
It isn't always cute.
Sometimes, the bending of rules leads to genuine resentment. If a son feels like his mom is letting him win, it can actually hurt his self-esteem. It sends a message: "I don't think you're good enough to beat me fairly." On the flip side, if the son is constantly cutting corners and the mom feels she has to police him like a drill sergeant, the "fun" family night becomes another chore.
I remember a case study mentioned in a parenting seminar where a mother was genuinely distressed because her twelve-year-old son couldn't finish a game of Catan without "finding" extra resources. She felt like she had failed as a parent. But the reality was simpler: the kid was just anxious about failing. The cheating was a coping mechanism for the pressure he felt to be "the smart one" in the family.
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The role of digital "cheating" in the modern home
Everything is digital now. Mom and son aren't just playing Scrabble; they're playing Roblox or Fortnite.
Cheating here looks different. It’s "meta-gaming." The son might know a glitch or a shortcut that Mom doesn't. He uses his superior tech literacy to dominate. Is it cheating if one player simply knows the system better? Probably not. But when a son uses his mom's account to buy "skins" or upgrades without asking, or uses a lag switch to win a match, we've moved past "house rules" into actual behavioral issues.
In these digital spaces, the mom is often at a disadvantage. She might not even realize he's "cheating" until she looks at the credit card bill or sees him gloating over a win that didn't seem physically possible. It changes the dynamic from a shared activity to a lopsided exploitation of knowledge.
Why we should—and shouldn't—care
Look, in the grand scheme of things, a little bit of mom and son cheating at Sorry! isn't going to collapse society.
In fact, some child development experts suggest that testing boundaries in a safe environment—like a game—is a natural part of growing up. It’s a low-stakes way to explore the consequences of breaking social contracts. If he gets caught, he loses the game or gets teased. It’s a "safe" failure.
However, if the behavior isn't addressed, it can bleed into other areas. If Mom always covers for him or allows the deception to continue, she might be inadvertently teaching him that the rules don't apply to him as long as he has an "enabler." That’s where it gets messy.
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Breaking the cycle of "Dishonest Play"
If you've noticed that your game nights have become a den of thieves, it’s probably time to reset. It doesn't have to be a big, dramatic "family meeting." Just change the way you approach the table.
- Call it out early. If you see a hand moving toward the bank, say something funny but firm. "Nice try, Houdini, put the twenties back."
- Stick to the RAW (Rules As Written). For one night, try playing exactly by the book. No "Free Parking" money. No "mercy" re-rolls. It might be frustrating at first, but it levels the playing field.
- Choose "Co-op" games. This is the ultimate fix for mom and son cheating. If you're playing Pandemic or Forbidden Island, you're on the same team. You win together or lose together. If he cheats here, he’s only cheating himself, and it usually stops the competitive friction cold.
- Discuss the "Why." If the cheating is constant, ask him why he feels he needs to do it. Is he bored? Is the game too hard? Is he just trying to get a reaction out of you?
Practical steps for a fair game night
If you want to move past the era of mom and son cheating and actually enjoy your time together, you need a strategy. This isn't about being the "fun police." It’s about making the victory actually mean something.
First, let go of the need to protect his feelings. If he loses, he loses. Learning to lose gracefully is a much more valuable skill than winning a plastic trophy through deception. Most kids are more resilient than we give them credit for. They'd rather lose a fair game than win one they know was rigged.
Second, vary the types of games you play. If he's cheating at strategy games, try a game based on luck or physical dexterity like Jenga. It's a lot harder to "cheat" at gravity.
Finally, lead by example. If you, as the mom, are cutting corners to "keep the game moving," you're giving him a green light to do the same. Play with total integrity. Show him that the fun is in the process, the laughs, and the near-misses, not just the tally at the end.
The next time you sit down to play, leave the "house rules" in the drawer. See what happens when you both play it straight. You might find that the game is actually more exciting when the outcome isn't guaranteed by a little bit of under-the-table maneuvering.