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Woman Lays Into Brother After Learning He Plans To Ask Out His Married Boss

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There are several downsides to having a crush.

Wondering if said crush likes you back, worrying how you’ll behave around them, finding yourself distracted because they take up most of your thoughts.

Perhaps worst of all, however, is misconstruing their behavior and thinking that they are expressing interest in you, which may not be the case.

Much as we might try to deny it, just about everyone who’s ever suffered from a crush has found themselves in this unfortunate situation.

Such was the case of Redditor Evil_sister‘s brother, who planned to take the big step and ask their unrequited crush out on a date.

A plan the original poster (OP) wasted no time convincing her brother not to do, and making no effort to mince her words.

Worried that she may have been out of line, the OP took to the subReddit “Am I The A**hole” (AITA), where she asked fellow Redditors:

“AITA for telling my brother that his boss is out of his league so he should give up?”

The OP explained why she felt no guilt or shame in explicitly telling her brother that asking his crush out on a date was a colossally stupid idea.

“My (29 F[emale]) brother (33 M[ale]) started working at a new firm.”

“He is working there because I asked my husband’s cousin, (36 M) his boss to hire him as a ‘family favor’.”

“My husband’s cousin owns this firm so it wasn’t a problem for him to hire my brother.”

“Like two weeks later my brother started telling me that he was attracted to his boss and found him handsome.”

“My brother is bisexual and when he found out that Jeff, his boss, is gay, he went crazy about it, because he likes him.”

“Here is the thing, my brother knows Jeff if married to Liam, his husband, and has a four years-old son with Liam.”

“My brother thinks that as Jeff is nice and polite to him, Jeff is into him.”

“My brother came to my house yesterday and told me and my husband that he was planning on asking Jeff out.”

“I mean, I am pissed off because he is talking as if Jeff was single so I told my brother ‘ok, let’s ignore the fact that going after a married person is wrong and morally incorrect, do you think he’d leave his handsome husband who is an engineer and makes twice what you do and who he has a child with for you?'”

“‘A man he just met?'”

“‘C’mon buddy, he is completely out of your league, he has a great job, a handsome husband and happy family with a child, if he leaves his husband would be for the better and not the worse’.”

“My brother called me an AH for comparing him to Jeff’s husband.”

“My husband says I’m TA because I was too rude and made a big deal over a feeling, my mom called me rude on my brother’s feelings.”


Fellow Redditors weighed in on where they believed the OP fell in this particular situation by declaring:

  • NTA – Not The A**hole
  • YTA – You’re The A**hole
  • NAH – No A**holes Here
  • ESH – Everyone Sucks Here

The Reddit community overwhelmingly agreed that the OP was not the a**hole for scolding her brother and telling him his boss was out of his league.

Everyone agreed that harsh though the OP’s words may have been, the behavior of her brother was arrogant and narcissistic, and thus he needed a serious reality check which the OP provided him, with several surprised how he didn’t take into account how it could negatively affect his employment.


“Sounds like your brother is an idiot who needs things laid out for him as plainly as possible.”-Hitzsheila


“Your brother is a major AH for even considering breaking up a family, not to mention potentially tarnishing your reputation for getting him the job in the first place.”

“Your husband is an AH for trying to spare the feelings of someone who cares less about breaking up a family than their own sexual gratification and ego.”- Leafburn


“You should ask your brother if he is fine with being a home wrecker because that’s what he wants to be.”

“As his boss, Jeff should be polite to your brother and to his every other employee.”

“Being attracted is one thing, but acting on it will have consequences.”

“I wouldn’t be surprised if it hurt your brother’s career or even got him fired.”- RedSAuthor


“If anything you did him a favor.”

“Not only is Jeff married, but his inevitable refusal of your brother’s advances may also make things very awkward at his relatively new workplace.”

“No one wants that dynamic.”- CompelledToLacerate

“NTA I probably would have just told him that sexually harassing his boss is a bad career move, and in the words of Don Draper, don’t sh*t where you eat.”- Bloodrayna


“He got his feelings hurt because you told him a few truths but he is ok with braking a family?”

“Anyone that thinks you are wrong, is an AH too.”- woman0912873465

“I’m gonna go with NTA here.”

“Your brother is out of line and you just pointed out reality.”- Interesting-Month-56


“You need to tell Jeff what is going on.”

“Your brother has a deluded crush and the rest of your family, including your husband, are encouraging him in this.”

“He is going to do something that should get him fired and if Jeff doesn’t know why he might keep your brother on out of family loyalty.”

“When he does something bad enough your family will blame you and/or Jeff.”

“And what if he tries to sabotage Jeff’s marriage?”

“You could have been nicer about it, but he certainly doesn’t deserve it.”- Natural_Garbage7674


“You gave your brother a reality check that he desperately needed.”

“Now it’s up to him whether he wants to return to reality or continue on his delusional path.”- Willing-Rip-8761


“Siblings, especially younger siblings, for some reason, are experts at sniffing out BS and calling it what it is.”

“Your brother was contemplating a foolish, harmful act.”

“Good for you, doing your duty as a sibling!”- candlestick_maker76


“If the boss were single, I might say ESH because you were very harsh.”

“But the boss is married with kids and he doesn’t care?”


“Plus, sexual harassment, anyone?”

“Good job giving him a reality check.”- hypothetical-ginger


“Your brother sounds so selfish.”

“If I were you, I’d wonder what are your husband moral about cheating.”

“Sounds like an interesting convo.”- Prize_Fox_9163

“NTA and your brother is gonna get fired.”

“Asking out your married boss is an extraordinarily stupid thing to do.”- Eastern_Fox5735

“Absolutely NTA.”

“His boss is married and has a child.”

“Did we also mention he’s his boss?”

“That’s 3 reasons not to ask or pursue this man.”

“Your brother’s intentions have bad idea written all over it.”

“Plus he’s putting his own employment in jeopardy if he does this.”- WinEquivalent4069

“If I was OP.”

“I would go to the cousin and be like, ‘Hey, so my brother has this stupid idea that you’re into him and he’s going to attempt to ask you out’.”

“I already discouraged him(for obvious reasons) but I thought I’d give you a heads up.”

“And let your cousin take it from there.”- zombykiller87


“You can add on that asking people out in the work place is a recipe for sexual harassment issues and he needs to not unless he wants to lose the nice new job you just helped him get.”-NerdySwampWitch40


“In this situation, I feel like you are justified in using almost any legal means short of physical force to make your brother to keep his d*ck in his pants.”

“If your brother makes a pass at his freaking married boss who is your cousin-in-law it is not only going to be incredibly bad for him, it is going to be humiliating for you.”- IanDOsmond


“But you really should have warned him that by actually asking him out it could be seen as sexual harassment and he could get fired from the job you helped him get.”- Glenn_Coco69


“If your brother is trying to be a home wrecker, even if Jeff doesn’t think about your brother in any way other than employee and being polite is just how he is, then it’s a good thing that you gave him a reality check.”

“He doesn’t sound like the type to listen to you calmly telling him that it’s not right to try to break up a family and if he tries something then he’s going to get fired and embarrass the entire family and your husband’s family would be mad too and you’re not going to have your in laws be upset at you because of his crush.”- Kooky-Hotel-5632

The saying “don’t dump your pen in the company ink” exists for a reason.

Hard as it is for anyone to be told someone is out of their league, the OP was likely aware that hearing just that was likely the only way it could possibly dawn on her brother that his decision was a bad idea.

One can only hope he heeded her advice, and did not ask his married boss out on a date.

Otherwise, he might soon find himself in need of another job.

Written by John Curtis

A novelist, picture book writer and native New Yorker, John is a graduate of Syracuse University and the children's media graduate program at Centennial College. When not staring at his computer monitor, you'll most likely find John sipping tea watching British comedies, or in the kitchen, taking a stab at the technical challenge on the most recent episode of 'The Great British Baking Show'.