When will we[me 30M] [her 30F] be able to be friends again? Is that even a possibility?

I will preface that not only do we work together but her dad is long time friends with our boss, who is usually pretty cool but, it’s still a weird situation from the outside. We also both got out of romantic relationships last year, if it matters.

We had known each other for most of last year and one day she asked me out to drink, we didn’t put a label on it just went out, had a great time together, got to know each other, got a bit tipsy and a bit handsy with each other, at her apartment and her bedroom, feeding each other, sharing wine glasses, just getting very comfortable, but the night ended once she had to throw up. She had asked me to stay the night if I wanted to but understood that I needed to go home

Since then she’s been weird on some days at work, completely ignoring me at times, but on others being all over me, leaving with me, waiting for me, but never wanting to actually do anything together besides getting high at her apartment a few times a month

I’m very reserved, especially in a professional setting, so I mostly talked to her when she came to me during and after work, and she kept coming, seemingly getting very comfortable touching me especially if we were alone in my car or on the bus, getting cute and doing voices around me, showing me her real side, always stopping me at lunch to eat together or simply hang out that time.

Twice even told me to stay at her apartment if I needed to get away from my roommates’ noise, and kept remarking how I’m not like other (creepy) men, one day even thanking me for always being there for her and taking care of her. She always showed an interest in my outdoor activities, which was nice, and said I’m the type of guy she would like to be on the outdoors with

I decided to stop wondering about all the dot connecting and just asked her out one day, and she said yes! She seemed happy, even helped me plan the date. Day of date, though, she asked me if we could do it tomorrow. Then the next day she again had to move it, asked me to please not hate her, and chose the next weekend. Hey she rescheduled twice but at least she kept the date on, I thought.

Next weekend she fell ill, I saw she was a bit during the week, and cancelled again, didn’t say another day this time nor did I push it cause third time you know, and she thanked me for understanding. She kept texting me about work on her way to the doctor and at some point I stopped texting her. Maybe I was bored, maybe hurt and she continued talking, not sure. That night I asked her how it went and she never answered

The next week was my last week before two week vacation, and since she flipped back to avoiding me at work on most days, I texted her asking if she wanted to do the date when I came back, but never answered that either. My last day I said goodbye and it was a very awkward goodbye and it has just been weird between each other since that week. Neither of us is talking much if at all to each other, though admittedly I rarely talked to her unless she came to me or we ended up having lunch together at the same spot at work

I feel like the first day I came back I went by her table to say hi to her and others and she didn’t say anything, and the next day she asked me something in the kitchen and I might have, not in a rude way at all, being short with her and told her to ask someone else that would probably know instead of taking it as an opportunity to talk to her- I was a bit busy.

Since then we only share glances when we go past each other and/or say bye at the end of the day but again only if we go past each other. Just raising her eyes on her part and a small smile on my end. If we’re standing close to each other I’ve noticed her at times just looking down or away

And it sucks since we used to be so close before all this and now we seem to not even know nor want to be around each other. I definitely don’t want her to feel I don’t want to be around her or that I’m upset or anything. And it’s hard to convey that if I’m just giving her space, and I’m taking cues from her that that is what she wants, space. Or maybe she is taking cues from me and I haven’t noticed I’ve changed the way I’m acting, or is waiting for me to talk to her, initiate a conversation. Then again I thought the same thing about asking her out so what the hell do I know

I feel we might have reached a peak that night we went out but never talked about it. Never seen her so happy in the time I’ve known her, she called it the best night ever, and truthfully hadn’t felt as happy myself in a long time until then. And now I have to always be around someone with whom I feel I had obvious mutual attraction but never know what could have happened, and have them become an estranged friend. It really feels like we’re not even friends anymore.

She’s told me she’s on medication which I’ve used to explain her odd behaviors before asking her out, and she knows well about my own mental problems, but I doubt that’s what’s going on and we always share with each other when we’re doing through difficult times

I knew the risk and I took it but it does suck to live it. Yet I don’t know if she doesn’t like me, if she does and is hurt, if she never did and said yes for some weird reason, if she kept rescheduling to delay, if she did want to but feels I wronged her, if she just changed her mind, if the situation with her dad and boss is in her head- I have no idea what to do nor feel right now, but overall I miss her, and I really don’t like how things are between us. Thanks for reading, any advice or just words are very much welcome

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**tl;dr**: Friend from work and I got very comfortable with each other, decided to ask her out, she said yes, moved date three times, ended up nowhere, now it’s weird when we’re around each other barely even speaking. Want to be friends again or whatever but it seems unreachable right now