I broke every dating “don’t” and may have paid the price

This is a part vent/part giving advice/part open to support but above all, a cautionary tale. I realize what's happened here and what I've done is controversial, especially on the dating subreddits. But I know there are people on here who fall into the categories of the situation that I was in. Interested in their coworkers. Interested in their friends. Interested in their roommates. I (32F) got into a thing with Jeremy (29M) who was all three.

September 2024 I started working at a new job. Gained a crush on Jeremy who was charming and friendly. I wasn't ever seriously considering pursuing it but I found out he had a girlfriend a few months in and shut those feelings down in myself. He broke up with his gf, crush came back a little bit as I allowed it.

Then I heard he was looking for a new place to live as he was separating from his ex. I offered for him to move in with me because I needed a roommate. We hung out early April 2025 to do some pre-roomie bonding and quality time and got into deep convos. It was emotionally intimate and made me feel The Feels^TM but, he was moving in. I shut it off completely in my mind. He moved in in May.

Often we work our shifts literally 2 meters away from each other. I learned after the fact that many people thought it would crash and burn because they didn't think it would work out, we were too different. But he was actually one of the best roommates I've had. We became very good friends. Had many more deep and lengthy convos. Many things where he said he'd "never told anyone this before". Sometime September 2025 he had a health issue and I realized that I really cared deeply for him like I do as family. Unconditional love. We'd literally say "I love you" to each other.

Halloween came and he told me it was time for him to move – needed a place where he could have his dog that his ex was keeping at their old place. After another deep conversation he tried to kiss me. I said no, there are lines we do not cross. Then he asked for cuddles. I agreed to platonic cuddles (which I've done with a few friends but only works if you're single or non-monog, because cuddling as adults is odd and might cross relationship boundaries). While cuddling he said some things: he wanted to have sex, but it was really confusing because I was such a good homie, but I was beautiful, and I knew how he felt about me – which I did at the time because he'd been very expressive about how he admired how I lived my life and aspired to be like me. I declined and nothing really happened besides his slightly wandering hands and handholding.

But then over the next couple weeks I kept thinking about it. He was only home at that point maybe 1 night/week because he was taking care of his dog at his old place. Mid November he came back one night and I brought up sex. We set some ground rules. His were "all I want to do is respect you and not ruin our friendship". So we were sleeping together every week-ten days or so. A couple times literally just sleeping together. We had many convos about our dynamic during that time where he said the same thing, he didn't want to wreck our friendship. I said I thought that of all the people that I've slept with, worked with, or been friends with, I didn't think I'd have been able to be in the same situation with any of them. It was by far the craziest dynamic I've ever had and the potential for fallout was collosal. But we communicated well and I had every reason to believe that no matter what, we'd be able to be friends above all.

He moved out ten days into January. We actually started talking at work a little more than we were when we were living together. But a week later he switched up, I kept asking how he was doing and he'd usually just give me "I'm tired/I'm focused" and so I'd leave him to it. Gave the benefit of the doubt that everything was fine. But it continued, and he just kept saying the same thing every time I saw him. Meanwhile he'd be talking to everybody else all around me.

I was confused, felt brushed off. Communicated exactly that to him. And things just kept getting worse and worse and the ignoring got really blatant.

I was so hurt and confused and sad. Ultimately couldn't really figure out what the problem was and what changed, because I'm not in his head, but a number of my thoughts came down to one fundamental thing. That I'd lost one of my best friends because I slept with him. After the first week of February I stopped trying to communicate and fix things.

All his friends/the boys who hung out at our place so many times were still friendly and talkative. And supportive of me when they got kind of clued into what was(n't) going on between us w/regards to us not talking.

So the point of all of this is to say.. sure, you can do it. You can pursue your roommate. Or your very good friend. Or your coworker. You can do all the right things and communicate to get on the same page. There really might not be any fallout if things go sideways if you are clear with expectations. But there's still potential for consequences that you may have no possible way of knowing. You can never know, none of us can predict the future or emotions that come up. So tread very carefully.

As of now, things may be turning around a bit. The "may" is doing some pretty heavy lifting there. Two weeks ago I was encouraged by one of the boys to try again. I asked Jeremy if it was time to chat to sort things out and he actually said "yeah" although no solid plan. He pulled the very shitty move of trying to booty call me the next night. Told him wtf, I didn't want to have sex with him after he's been a prick towards me for almost two months. But also before he brought up sex he said some things like he missed me, he was ready to talk, he'd spill his heart out, he was afraid of his feelings before. Then the next day apologized for it all. Still no follow-through on having a chat though.

I called him out a few days ago through text. We had a heated and long exchange through messaging. Some things are more clear now. But my guards have gone up despite me trying really hard, through trying to fix things with him at first, to not have that happen. And so now I'm just waiting to see if he's going to put his money where his mouth is and actually try to fix things, so that he "doesn't lose me as a friend over his idiotic behavior". I hope things do work out. I have some optimism. But also not willing to put much more work into this to push things forwards and I'm skeptical. And still feel like I have to accept I really may have lost one of my best friends because of all of this. I hope we can go back to what we had before sleeping together. But have to accept that we might not. Which is devastating.

Even when you really think you know, you can't really know. I wish I could take all of it back, but I can't so I just have to live with it.