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Should I ask him?

I think I already know the right answer. Which would be to tell the guy I have romantic feeling for him, but a little backstory.

There is this guy who used to be my boss and later I became a manager, so we were colleagues. I have had the biggest crush on him for a long time, but besides working together he had a girlfriend at the time. I did not want to be a "home- wrecker" for his relationship and I wanted to keep a good professional working environment. I don't believe in dating people you work with. It causes too many problems imo.

We have both moved on from that job and his girlfriend broke up with him a while ago now. We still keep in touch and hang out occasionally. From working with him on a lot of late night shifts we became close friends. I've heard from some people who worked there that he was interested in me. Although I thought it was them wanting to stir up the drama-gossip mills at work. He hasn't made any moves to ask me out and neither have I. I don't know if it's because he's uninterested now or if we're both too shy for our own good.

The only thing besides being shy, that has kept me from asking him out is that I have a serious fear of relationships. Especially committed ones. I have dated a bit, but I struggle to allow myself to be vulnerable. I like to be able to drop a relationship with little attachment on my end. Which is counterintuitive to a good partnership. There are very few healthy relationships I have witnessed in my family. I do not want to follow in their footsteps of a life full of problems from bad screenings for a life partner. I understand that all relationships are about compromise, but what shouldn't I compromise on?

This guy has been one of the few people I've connected with and been vulnerable with. Probably because I thought I'd grow out of my "crush" phase. We've known each other for 5 years now and that hasn't faded. I just don't know if I'm in love with the idea of being in a relationship with him because it's been a slow burn at this point. I want to ask him to give myself closure, but I also don't want to loose him as a friend. I do not want to be a jealous bystander for the rest of eternity. I was already that once and I hated myself for it. I already think I know the right answer as stated at the beginning. But I thought this would be a good space to get advice or give me courage to speak up.

Sorry for the long post.

Thank you for taking the time to read this through. ^_^ ♡


New Member
I think you should talk with him and explain your feelings. It always helps me. But you must be ready that it destroys your labor relations if this is not mutually.