April 12, 2025 at 12:15 pm

She Was In A Wonderful Relationship With A Great Guy, But Then His Old Friend Showed Up With An Ultimatum That Wrecked Everything

by Ben Auxier

Shutterstock/Reddit

Some old flames just never die. In fact, sometimes they burn everything around them.

Like in this story where a “friend” gave her new man an ultimatum: it’s either her or me.

What a dilemma!

Let’s find out what happened…

AITA for breaking up with my boyfriend after he chose me in an ultimatum?

Me (27F) and my boyfriend (27M) have been dating for four months.

We have so much in common, he’s super sweet and always goes the extra mile for me with grand romantic gestures, even asking me out by buying me my favorite comic book and leaving a sticky note between the pages confessing his feelings.

I’ve never gotten anything but amazing vibes from him this whole time until now.

All was fine and dandy, though Syd lurked in the shadows.

However, BF has a childhood friend (27F) I’ll call Syd.

My boyfriend was very upfront when we started dating that he and Syd had romantic feelings for each other in the past but decided it would be best they only stayed friends since they didn’t want to risk their friendship.

I never actually met Syd before and have only heard about her from BF and vice versa.

Then, seemingly out of nowhere, Syd struck.

About two weeks ago, my BF texted me, super distraught, telling me that Syd called him, saying that she was too jealous of my and BF’s relationship and that she couldn’t stand being BF’s friend while he was in a happy relationship with me.

She basically gave BF an ultimatum of him having to break up with me or she would cut him out of her life.

I was baffled by this, thinking that this 27 year old woman, who had mutually agreed with BF that they would never date, was so childish to give him a ridiculous ultimatum and I voiced that to him.

He got mad at me, saying “It’s not that simple” and seemed to be seriously considering breaking up with me just to stay friends with Syd.

This seems like a pretty obvious choice to most of us.

I was in disbelief that he couldn’t see how manipulative and abusive this was, and that the obvious conclusion would be to cut her off since she was clearly toxic and controlling, but he was still on the fence and we ended up taking a break and not talking while he “thought it over.”

The next week and a half, he barely talked to me, telling me he’s in a very hard place while I became increasingly frustrated that this would even be a hard choice.

Like, we’re in a happy relationship, and he’s debating breaking up because his crazy friend can’t handle her jealousy? I was fuming.

And then, after entirely too much deliberation…

He then finally came to me after that time of not talking saying he decided to “choose me” and leave his friendship with Syd behind, but by that time I was so mad that it was even a choice that took two whole weeks to decide to begin with that I ended up breaking up with him anyway.

She’s dealing with the aftermath now.

Now his friends are telling me I’m an ******* for not breaking up with him sooner because now Syd is still cutting him out for picking me over her AND I’m still leaving him, whereas if I had broken up with him during the weeks he was “thinking it over”, he would have at least been able to stay friends with Syd.

But honestly, I didn’t even realize how mad I was until he picked me and made it seem like he was some kind of martyr for doing so. AITA?

What do the comments make of all this?

2025 03 26 18 54 56 She Was In A Wonderful Relationship With A Great Guy, But Then His Old Friend Showed Up With An Ultimatum That Wrecked Everything

There was zero chance she was just going to go away.

2025 03 26 18 55 07 She Was In A Wonderful Relationship With A Great Guy, But Then His Old Friend Showed Up With An Ultimatum That Wrecked Everything

I could understand if this caused him distress, but the decision itself should have been obvious.

2025 03 26 18 55 13 She Was In A Wonderful Relationship With A Great Guy, But Then His Old Friend Showed Up With An Ultimatum That Wrecked Everything

Some growing up needs to happen.

2025 03 26 18 55 24 She Was In A Wonderful Relationship With A Great Guy, But Then His Old Friend Showed Up With An Ultimatum That Wrecked Everything

What was really going on here?

2025 03 26 18 55 51 She Was In A Wonderful Relationship With A Great Guy, But Then His Old Friend Showed Up With An Ultimatum That Wrecked Everything

He’s shown you both he doesn’t know what he’s doing.

2025 03 26 18 55 44 She Was In A Wonderful Relationship With A Great Guy, But Then His Old Friend Showed Up With An Ultimatum That Wrecked Everything

Seems like you made the right call.

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