May 31, 2026 at 8:20 pm

Woman Considers Dating Her Best Friend’s Ex-Manager, but Her Friend Threatens to End Their 15-Year Friendship Over It

by Heide Lazaro

Man and woman casually dating

Pexels

True friends should support your budding relationship…unless they have a very good reason not to.

In this story, a woman considered dating her best friend’s former manager, despite knowing her friend had a difficult history with him.

The friend got upset when she learned about this and told her to stop engaging with him.

When asked, the friend refused to explain the full situation.

As tensions escalated, she was forced to choose between potential romance and a long-standing friendship.

Uh oh! That sounds like a difficult decision to make. Let’s take a closer look!

AITAH for considering dating my best friend’s ex manager whom she hates?

Both my best friend and I used to work for the same company. We were in different teams.

Last year, the company was going through a rough financial period.

Her manager had to lay people off. She was one of them.

Fast forward to this year, neither of them works at the company anymore.

This woman started engaging with her best friend’s former manager.

Since then, her former manager has been texting me regularly.

I have been engaging in the conversation.

When she found out we were texting, she completely lost it. She told me I could date anyone on earth except him.

Whenever I asked her why, she refused to tell me.

Her friend wouldn’t give her a good reason on why she should stop the relationship.

From what I have gathered, there were situations where he lacked empathy toward her.

He made her believe that others had said bad things about her. That was not even true.

She will not go into more detail. She says I should not be the one deciding what is hurtful enough or not.

I kept telling her that if she does not explain, it is hard for me to understand.

They got into a huge fight.

I asked why I should not date him.

She says it does not matter and it is about loyalty.

This turned into a huge fight. She had a breakdown for three full days. This is not an exaggeration.

She told me that if I ever go on a date with him, she will immediately end our 15-year friendship. This applies even if it is just a fling.

Now, she’s thinking about still seeing him in secret.

For context, my best friend and I are like sisters. We have been friends for 15 years.

I am invited to all their family gatherings.

They consider me like family.

So, AITA for still considering seeing him in secret?

Honestly, the fact that she reacted this strongly makes it sound like there’s something more to the story that she wasn’t sharing.

Don’t you think? Is a 15-year friendship really worth throwing out just because of an ex-manager?

If you enjoyed this story, check out this post about a woman who was stunned when her friends finally admitted the reason for their falling out.

Hmmm… something doesn’t quite add up. Let’s see how others reacted instead.

Date who you want, says this person.

Screenshot 2026 05 15 at 3.13.25 PM Woman Considers Dating Her Best Friend’s Ex Manager, but Her Friend Threatens to End Their 15 Year Friendship Over It

This person gives their honest opinion.

Screenshot 2026 05 15 at 3.13.50 PM Woman Considers Dating Her Best Friend’s Ex Manager, but Her Friend Threatens to End Their 15 Year Friendship Over It

Short and simple.

Screenshot 2026 05 15 at 3.14.10 PM Woman Considers Dating Her Best Friend’s Ex Manager, but Her Friend Threatens to End Their 15 Year Friendship Over It

This person makes a valid point.

Screenshot 2026 05 15 at 3.14.27 PM Woman Considers Dating Her Best Friend’s Ex Manager, but Her Friend Threatens to End Their 15 Year Friendship Over It

Finally, another person chimes in.

Screenshot 2026 05 15 at 3.15.16 PM Woman Considers Dating Her Best Friend’s Ex Manager, but Her Friend Threatens to End Their 15 Year Friendship Over It

Sometimes, the biggest red flag is a friend who makes unreasonable judgments about your relationship. Without any real context about why her friend doesn’t want her to date him, it’s hard to justify ending a relationship she doesn’t want to end.

Heide Lazaro is a veteran human-interest writer and digital culture expert with over a decade of experience in editorial strategy. Specializing in lifestyle, social dynamics, and the internet's most compelling stories, Heide has authored and published more than 10 books online. Beyond her daily reporting, she is a dedicated motivational speaker who helps audiences connect through the power of storytelling. When she isn't sifting through the web's wildest real-life drama, Heide is an avid runner, painter, and novel-enthusiast fueled by a truly excellent cup of coffee.