AITA for laughing after my brother lost a game of chess?

In a living room thick with bravado, a man’s brother boasted he’d “teach a pretty girl” chess, unaware his opponent was a chess master. Nine moves later, his confidence lay in ruins, checkmated by the man’s girlfriend in seconds. The man’s laughter at his brother’s stunned defeat, followed by accusations of cheating, got them booted from the house.

The brother’s wife scolded the girlfriend for not being “gentle” and the man for his chuckles. This Reddit tale, buzzing with ego and comeuppance, echoes your own run-ins with family arrogance, like your brother’s overconfidence or your in-laws’ demands. Is he wrong to laugh, or did his brother’s hubris beg for it?

 

‘AITA for laughing after my brother lost a game of chess?’

My girlfriend is a chess master; which basically means she’s really f**king good at chess. My brother recently got into it, and seems to believe that he is the smartest f**king person alive for understanding how the game works as only “smart people can truly understand the art of chess” (his exact words)

My girlfriend and I went to my brother’s house to pick up some things. I’m under the impression that my brother believes my girlfriend to be a causal chess player. When he learned that my girlfriend played chess, he challenged her, remarking “it would be nice to teach a pretty girl about the art of chess,” and “she could learn a few things from him,”

My girlfriend was more amused than offended and took his offer.. The game was over in literal seconds. I don’t really understand how chess works, but I do know that he was checkmated in 9 moves. I found this all kinda funny; the change in his demeanour from overconfident to defeated so I laughed.

It was even funnier when he accused my girlfriend of cheating (how do you cheat in chess?) and said that she must have been lying etc. So, a few more laughs left my mouth. My girlfriend gave me a look so I stopped laughing, but he kicked us out anyway. My SIL is mad at me for laughing and at my girlfriend for not being more gentle in her win, claiming that she was purposefully showing off her skill.

Arrogance can set the stage for a hard fall, and this Reddit user’s brother learned that lesson in nine chess moves. His patronizing challenge to a chess master girlfriend, laced with sexism, backfired spectacularly, and the user’s laughter—though perhaps tactless—was a human response to the irony. The SIL’s demand for a “gentle” win reeks of gendered expectations, much like your own family’s push for you to accommodate unreasonable behavior.

Psychologist Dr. Susan Krauss Whitbourne notes, “Overconfidence often stems from fragile egos, and public defeat can trigger defensive outbursts”. Studies show 60% of people overestimate their skills in competitive tasks like chess. The brother’s accusations of cheating reflect a bruised ego, while the SIL’s reaction reinforces outdated norms.

The user could smooth things over with a light apology for laughing, as you’ve navigated family spats, while encouraging his brother to reflect on his assumptions. His girlfriend’s decisive win needs no softening—she played fair.

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Here’s the comments of Reddit users:

Reddit roared with glee, cheering the girlfriend’s swift victory and the user’s laughter, while torching the brother’s sexism and the SIL’s bias, with a sprinkle of humor to keep it lively. Here’s what they said:

Accomplished_Sun_258 - NTA. ... and your brother sucks.. My SIL is mad (.....) at my girlfriend for not being more gentle in her win... Oh for the love of Pete! Thank you, Internalized Misogyny, for dictating that as a Vagina-Holder I need to be *gentle* when I win!

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Rhidds - As a 16yr old girl (22 yrs ago) I landed the perfect job for a girl who grew up with computer games, I worked in a game shop. As was often the case, we had a ps1 running demos or trailers on the tv in the shop. If people asked, we would pop a game in and let them play.

Usually kids would drop by and ask whatever new fighting game came out to play it. My boss was chill, would usually give them the chance. After closing, my boss and I would usually game together, quite often fighters. I have a competitive streak, so was determined to become good at these games. One day two kids came in, couple of years younger than me.

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They were loudly complaining that this place was no place for a girl. I’ve had to deal with nonsense like that my entire life and my boss knew this. He saw the look in my eye and asked the kids if they wanted to try the latest whatever fighter was popular. He did say they could play until closing if they could beat ‘the girl’. They eagerly accepted.

It didn’t end well. Even after applying as many disadvantages on myself, they still lost. After about 45-60 mins of this, they conceded and meekly apologised for doubting a girl can play just as well.. A week later they came back with friends to show me off.. NTA and your gf deserves a high five for what she did.

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nun_the_wiser - Hahahaahhahhaha NTA! He was being a jerk to your girlfriend, and couldn’t handle a quarter of that going his way

myra2106 - NTA, neither is your Girlfriend. If he is so arrogant he needed to be taught a lesson. And he shouldn’t play with fire if he doesn’t want to get burnt.

DrOxy_82 - NTA SIL is probably mad because she has to hear him b**ch about it. He shouldn't have underestimated someone's ability. He sounds like an arrogant p**ck that needed an ego bruising. IMHO

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Dagordae - NTA. Note that a 9 move mate means he SERIOUSLY screwed up from the first move on.

EloquentBacon - NTA, NTA at all, your brother dug his own hole and jumped in it when he said he wanted to teach a pretty girl about the art of chess. I love that your girlfriend beat him so badly. I also love that you laughed out loud repeatedly. Your brother got what he deserved. 

I wouldn’t feel bad about it at all. Your brother set himself up for all this. The only person your SIL should be mad at is her husband with his sexist comments. I’m disgusted that she was okay with her husband throwing his brother out of his home over his own misogynistic b**lshit. They sound gross.

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x_Kandinsky_x - NTA. Your brother set out to try and humiliate your gf and got served. Had he managed it the rules of sibling rivalry demand that he trot out the story at every family gathering for decades. Instead you now claim that right, well on behalf of your gf should she agree that is, it is after all her victory.. ​

Also chess isn't a 'kind' game, your brother should know that, in chess you exploit every weakness and try to win as quickly as possible. Chess has been described as war on a board, the only game board game I know of that has a similar vicious side is Risk.. ​. ​ edit below - and this is why i don't play chess because it took me a few hours to think of this.

it could be that your gf recognised the potential for 'the long game' and that this early gambit play sends a very clear message to your brother, in the years to come do not underestimate me, this OP is my partner and i won't put up with any crap.. you, dear OP, may have found a unicorn of a partner, treasure her.

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[Reddit User] - NTA. If you’re going to talk a big game but not play a big game you deserve to be laughed at. It’s your fault that his fragile ego couldn’t handle a loss.

No-Jellyfish-1208 - NTA. He had it coming.

Reddit’s loving the checkmate, but are they missing the family fallout or just reveling in the burn?

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This Reddit user’s chuckles at his brother’s chess thrashing by his girlfriend lit a family fuse, with accusations of cheating and demands for “gentle” wins flying. The story, like your own tangles with family ego, asks where humor ends and sensitivity begins. Was he wrong to laugh, or did his brother’s arrogance earn it? How would you handle a family member’s humiliating defeat? Share your thoughts or stories of ego clashes and comeuppance!

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