November 11, 2025 at 5:15 pm

Man Fell In Love With His Friend And Ex-Co-Worker At A Time When He Least Expected It, But Their Relationship Is Causing Serious Drama In His Work Life

by Kyra Piperides

A couple at sunset

Pexels/Reddit

Falling in love is many great things, but no one ever said it was convenient.

And to many extents, we can’t choose who we fall in love with – because it’s about more than just aesthetics or sense of humour, it’s a genuine deep compatibility that often strikes you completely unaware.

While the absence of this feeling in a relationship where you might hope you’d conveniently find it, is stark.

So when the guy in this story broke up with his girlfriend, realizing something wasn’t right between them, he had no expectations – and he certainly didn’t realise he’d fall in love so soon, much less who he’d fall in love with.

Read on to find out how this affected things not only in his love life, but in his workplace too.

AITA For dating my ex-coworker after she rejected another coworker?

I am a 32-year-old man, and I started dating one of my coworkers (female, 31) shortly before she left this job for greener pastures (a better commute and better pay).

We started dating in a weird time in both our lives, but we were drawn to each other in a way we’d both never really experienced before.

We made it work and so far and are super happy together.

Read on to find out how their circumstances brought them together.

I’ll start with my weirdness. Earlier this year I ended a four year relationship.

It wasn’t an easy decision and I wish her only the best, it was just a series of events over the last year took the veil off my eyes to all the things about our relationship I didn’t like, and I decided that we weren’t a good match anymore.

It didn’t end poorly per se, but it didn’t end well either.

My now girlfriend and I were work friends for a while before all this happened.

Neither of us ever flirted or did anything outside of normal coworker interaction until a couple months after it ended. She was in the know for what I was going through since I confided in several people I worked with.

And there was some romantic instability in her life, too.

Now for her weirdness, which involves her and another and still coworker of mine.

There’s this guy I work with (a 28-year-old man) who had a huge crush on her, and at the beginning of the year he asked her on a date.

They were never officially dating and only went on three dates total over a three month period. She confided in me at one point that she thinks he’s sweet but that she’s just not interested in a relationship with him.

I told her that she shouldn’t force something she’s not into, among other advice I could think of at the time.

She thought about it for a while but ultimately told him that she wanted to stay friends but didn’t want to date him.

But that didn’t go down as she’d hoped.

Now, in an ideal world, that would be the end of it.

You try going out with a woman, she says thank you but no and you move on with your life.

This did not happen.

This guy would keep hanging on to her, flirt with her, and insist that she was hiding her true feelings.

And then, things changed for the both of them.

After my breakup happened, she and I started growing closer since the relationship barrier was down for me. We discovered more of our shared interests, our views and energy match, and our sense of humor is the same.

We talked more and more over text and on the phone. Eventually this led to us hanging out outside work, and I asked her to go out with me and we started dating.

We did keep this fact hidden from everyone at our work but specifically the guy who asked her out since based on his behavior he wouldn’t take it well.

She was planning to go to a new job soon so we decided to wait till he was gone to break the news, since at that point he was still her friend – though I suspected at the time he was only still there from some idea that he still had a chance to date her in the future.

Read on to find out what happened when they eventually told their co-workers about their relationship.

We had no obligation to tell anyone of course, but it was more of a courtesy since I would like to be able to openly discuss my personal life at work, and it would have come out eventually.

Well, to no one’s surprise he took it very badly. He called her a manipulative jerk who led him on, and a flirt who strings men along for attention (she’s not like that at all).

He then confronted me at work where he said things like “She ripped my heart out and you stomped on it.” He also said I was a terrible person for doing this to him.

I responded saying he was overreacting by a lot, that she had rejected him, and that they had never even dated for any length of time so it wasn’t like I stole her away. It was just two adults deciding to go out.

But this has left them in a place of turmoil.

The only thing I think we could have maybe done better is being more open about us earlier?

But I don’t think we did anything wrong.

AITA?

It sounds like this couple is meant to be together, and the adversity that they’ve faced is going to make them stronger in the long-run.

Their colleague, on the other hand, is a huge problem here. No means no, and she’s told him no plenty of times.

His behavior is immature, unprofessional, and hugely jealous.

Let’s see what folks on Reddit had to say about this.

This person thought they’d done their best.

Screenshot 2025 10 22 at 09.23.10 Man Fell In Love With His Friend And Ex Co Worker At A Time When He Least Expected It, But Their Relationship Is Causing Serious Drama In His Work Life

While others pointed out how weird and possessive the co-worker’s behavior was.

Screenshot 2025 10 22 at 09.24.40 Man Fell In Love With His Friend And Ex Co Worker At A Time When He Least Expected It, But Their Relationship Is Causing Serious Drama In His Work Life

Meanwhile, this Redditor suggested that if the situation persisted, he should get HR involved.

Screenshot 2025 10 22 at 09.25.10 Man Fell In Love With His Friend And Ex Co Worker At A Time When He Least Expected It, But Their Relationship Is Causing Serious Drama In His Work Life

His pettiness is clear.

If you liked that post, check out this story about a guy who was forced to sleep on the couch at his wife’s family’s house, so he went to a hotel instead.