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Guy Ends Engagement After Learning Fiancée Cheated On Her High School Boyfriend Nine Years Ago

Couple arguing on couch
Nick Dolding / Getty Images

Our past is as much about mistakes as it is about achievement.

For every celebration, there is some error in judgment that we learned and hopefully grown from.

So how long should we be held to the standard of our mistakes?

That was the issue facing Redditor and Original Poster (OP) broken_inside_me when she came to the “Am I the A**hole” (AITA) subReddit for judgment.

She asked: 

“AITA for kicking out my brother, who our parents have previously disowned, because he told my (now ex) fiancé that I cheated 9 years ago?”

OP began with an introduction.

“For reference, my brother Connor is 19, I am 26, and my (now ex) fiancé Hunter is 28.”

“Also for reference, already mentioned in the title, but my brother was kicked out when he was 16 because our parents snooped through his phone and found out he was in gay.”

OP explained the situation at hand,

“Connor had a birthday last weekend, so he invited his friends over, and they were all (18-22-year-olds) drinking and playing games.”

“Hunter and I were about to head out to let them have the place to themselves when Connor asked if we wanted to join them.”

“I initially refused (bit too old to be playing drinking games), but he insisted, and Hunter thought it’d be fun to act like college students again.”

“We all got pretty drunk, and Connor had the idea of playing Never Have I Ever.”

Everything was fine, until…

“A few rounds in, the statement ‘Never Have I Ever cheated before’ came up.”

“Now’s a good time to mention that Hunter is staunchly against cheating.”

“His ex-fiancé cheated on him, and it emotionally wrecked him.”

“And unfortunately, as a lot of dumb, immature 17-year-olds do, I cheated on my ‘boyfriend’ of 5 months.”

“It was a stupid mistake, he found out, and (understandably) ended things.”

“This was almost a decade ago, I obviously learned my lesson, and look back at that time with shame (and obviously never cheated since).”

“Well my brother knows about this so when I didn’t drink, he went ‘hey sis, what the hell? You know you cheated on (insert ex’s name). You have to drink to that!'”

“My boyfriend paused, looked at me, looked at him, and just walked out of the room.”

“I followed him and tried to talk to tell him that it was a stupid teenage mistake, but he wasn’t haven’t any of it and ended things on the spot.”

“I’m numb.”

“I’m heartbroken.”

“He was my everything and more, and I still don’t know how I’m going to move on.”

“Connor tried to apologize, but I feel nothing but sadness and emptiness.”

“This morning I served him an eviction notice.”

“He begged me to stay and said he didn’t mean to ruin my relationship and he just didn’t think when he said those words.”

“I just can’t look at him right now. He ruined my life. After I raised him and cared for him like he was my own.”

OP was left to wonder,

“I feel so hurt. Am I being unreasonable? AITA?”

Redditors weighed in by declaring:

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

Redditors decided: ESH

Responses were conflicted. 

“INFO – Did your brother know that your (ex) fiancé would have such a dramatic reaction?”

“I am not going to go all the way to saying you’re an A – but I don’t think you should kick him out over this, especially if he didn’t know how virulently opposed to you ever having cheated your fiancé would be.”

“Your fiancé, though – that is a big reaction. I’m not sure 100% willing to call him an A either, but … he needs to figure himself out.” ~ RLRicki

Some pointed out that OP was being hypocritical.

“I just want to be sure we talk about this on the same level.”

“You made a mistake as a teenager and should be forgiven because (1) you were a teenager and teenagers are stupid and (2) you learned your lesson.”

“But your teenage brother should be held to a high punishment for his actions…?”


“He was a stupid teenager when he pulled this.”

“You were a stupid teenager when you cheated.”

“You tried to lie to keep from any punishment but want to punish him for his mistake.” ~ SelfANew

“This is exactly why OP is the a**hole.”

“Kicking out a teenage boy because he said something during a drinking game that he had no idea would explode in everyone’s faces?”

“How can you even react like that when you are the one that raised that boy from 16 onwards? Does she really feel so little for her brother?” ~ hermionecannotdraw

“Your brother is barely older than you were when you made an immature teenage mistake by cheating on your boyfriend, and you certainly deserve to be forgiven for that.”

“It was a dumb move, but he didn’t mean any harm and seems genuinely remorseful.”

“We’ve all done dumb things without thinking as teenagers.”

“Don’t trash your relationship with your brother because of your fiancé’s issues. This is clearly not just about one instance of cheating as a teenager.” ~ kittykalista

Others suspected the toxicity actually belonged to the boyfriend.

“Reading OPs other comments I suspect it’s more to do with her relationship with her ex than that she doesn’t care about her brother.”

“He seems … controlling/manipulative, and I feel like her reaction to kick out her brother is likely the only way she can think of to show how much she wants to ‘keep’ her ex and apologize/grovel enough for his liking.”

“The whole thing sounds toxic tbh” ~ annshine

“One thing we know is the OP loves the ex way more than the ex loves her.”

“This massive power discrepancy in the relationship would have been a recipe for abuse anyway.” ~ MonkeyRexo

“I’m actually wondering about this equation here:”

“Fiance way overreacting”

“You don’t see anything weird about this”

“You are willing to throw away your relationship with your little brother you consider ‘like your own’ as a consequence.”

“I don’t think you’re okay OP.”

“To me, this is smoke that says there is a fire somewhere.”

“I think your fiance may have been gaslighting you on his bad behavior for a while to get you to this point.”

“You are walking on eggshells to please him and throw blame for his issues on anyone but him.”

“I know that these words get thrown around a lot on Reddit, but definitely don’t do anything rash until you sort it out, and seeking therapy is a great first step.”

“I have been thinking this one over and (without reading any comments replying) decided that gaslighting was an armchair psychology step too far.”

“What I really meant was that OP has become used to placating her fiance instead of compromising when they fight.”

“As a person who hates yelling and anger and avoids conflict, I can see how easy it is to always be the one making peace.”

“I feel like she’s become so used to it that she’s now accepting all responsibility for conflicts and not laying enough at his feet.”

“This is like gaslighting adjacent but maybe not intentional on the fiance’s part.”

“OP is getting professional therapy already, so it’s not really a harmful suggestion to throw out for the sake of discussion, but I also feel like it’s an extreme that the information given doesn’t warrant.” ~ AzureShell

Responses were very thorough.

“I’m going to have to say ESH.”

“Why your brother is TA”

“Bringing up your regretful teenaged mistakes is a huge no-no.”

“I don’t know why he would think exclaiming to everyone ‘hey everyone, my sister is a cheater’ was a great move, but I get that it was because he was drunk.”

“Alcohol does make you do stupid things.”

“I can easily see how the lack of judgment caused by inebriation could lead to him thinking that was an acceptable thing to do.”

“Why your fiancé is TA”

“Probably the most controversial of them but I think your ex-fiancé sucks the most.”

“I get being hurt in the past because of cheating (I know that pain all too well), but he’s holding a mistake you made when you were a teenager against you.”

“Assuming you’re being honest, you never cheated on him, you’ve never given any indication that you did, and the relationship was otherwise fulfilling.”

“Breaking off an engagement over something you did a decade ago is overkill.”

“Why you’re TA”

“You’re misdirecting your anger.”

“I get being upset because your fiancé left you, but I think that’s more of a fiancé problem than a brother problem.”

“From your story, he wasn’t being malicious, and he’s obviously remorseful.”

“No great relationship should end that suddenly and without warning, especially considering it happened a decade ago.”

“I wouldn’t let this blimp ruin an otherwise good relationship with your brother. Forgive him.” ~ [deleted]

Large or small, our errors will always find us.

There is nothing we can do to fix an error that we made, whether that mistake was a day or a decade ago. But that doesn’t mean we can’t try to hold ourselves to higher standards.

Written by Frank Geier

Frank Geier (pronouns he/him) is a nerd and father of three who recently moved to Alabama. He is an avid roleplayer and storyteller occasionally masquerading as a rational human.