Good day manly men of the interwebs, I come seeking your wisdoms. Bit of a long one, so do strap in (and thank you in advance for your patience, kindness and understanding).

There’s this girl (let's call her M) I went out with once right at the start of grad school in Oct 2021, and though it seemed like we had a good time, she ghosted me. What I was not aware of then, and would learn many months later, was that she was quite fresh out of a very long term relationship and was “new” to dating again and hence, freaked out. I did eventually get an apology for the ghosting, which I appreciated.

About a month later I get hired to be a staff writer on one of the school’s journals and Lo and behold, who should be the editor. I figured, what the hell, we can be professional, and admittedly, we worked quite well together, and eventually became friends, as we ended up seeing more of each other at social things through mutual friends. No problemo.

Come March 2022, she starts dating one of my very closest guy friends (call him R), and they get quite serious quite quickly. Having now reflected on this time, I suspect I still harboured some infatuation (sidebar: not a fan of the word, always makes a situation sound juvenile in my opinion, but that’s a discussion for another day) for M at this point, lingering some place in the back of my mind, but I shut it down in recognition of the relationship. I also did not want to be that friend to R, who was only friends with him, and not with his partner, and not comfortable spending time with both of them together or either alone so I made an effort to get to know this girl even more, and I came to find out that we were even more similar and aligned than I’d previously known. Even came to be a joke at one point that R was only dating M because she was a female version of me.

Summer rolled around, I went travelling, and the two of them went home to their families and travelled around a bunch over the summer, met each other's families, the whole schebang. R was planning for a move abroad as part of his dual degree program (he's not moved yet, he will soon), and M and I had some deep conversations about long distance, and maintaining connections, which led into other conversations about life in general, and we got to know each other even better on a much deeper level. Come September, M and R moved in together in City X while interning there (our school is weird, we have one semester at the start of second year that’s for internships and thesis writing and such), and I continued on in City Y (where we go to school), writing my thesis. Went out to visit them in November, and I came away thinking that it was like visiting my parents, like visiting a couple that had been together for 20 years, and not one that had been together for 9 months. What I’d suspected (correctly, as it turns out), was that the relationship had stagnated, and had ceased to develop any further - two people co-existing in the same space but not living together.

Fast forward to January, start of the new semester. R's on a gap year before he moves abroad, so he’s not back to school, but M is back in City Y, and she and I being friends, and having classes together, we did spend time together, I had her at my birthday party, etc. Great. Couple of days after my birthday, I get a text from R asking if I was free to chat. I was at a bar when his text came through, so I didn’t see it until I was on my way home – which is when M texted me asking if I’d heard from R, and quite cryptically mentioned that if I didn’t want to speak to her again, she’d understand. My mind jumped to worst case scenarios like someone cheated, or fell for someone else, things of that nature. Got R on the horn about a half hour later and he told me that M had broken up with him, because she felt the relationship had stagnated, wasn’t going anywhere, and that she’d fallen out of love with him. As any good friend would, I stayed up chatting with R, and left M a couple of messages too, saying if she wanted to talk, I’d be there. Having been in a position where mutual friends picked sides without knowing all the facts and hearing all the stories after I initiated a breakup, I knew that I didn’t want to inflict that kind of pain on either of them. Did not, and do not ever want to be that friend. R came out to see M one last time that following weekend, and in truth, was quite harsh on her (and this comes from mutual friends too, so not my own biases here), but I chose to keep my mouth shut because he was hurting, and my job as his friend right then and there was to support him, and get down in the mud with him. I took him out, we we ate, we drank, we made merry, and we talked. A couple of days after R left, I spent an afternoon with M. We talked about the breakup, I got her side of the story about the stagnation (and I shan't get into details here – ironic, I know), and we spent the next few hours just walking and talking about many things. That was about two months ago.

A couple of weeks ago (and this is where the problems start), M invited me to a party at her apartment complex along with another friend. We all had a few drinks, had a good time, good talk at M's place after we got bored of the party, all that good stuff. Twenty minute walk back to my place, and I could not stop thinking about her the entire way home. Figured it was just the booze, and that I'd have a clear head in the morning after a good night's sleep. But no. Still in my head, and stuck there since – and I've since realised that I've got real feelings for M. (Yeah, fuck me, I know)

If you've made it this far, thank you again for your patience and this is the real meat and potatoes of the dilemma here. Been a few days of thinking and guilt since. I know for a fact R is still hurting, and though he's being petty about a great many things (which I do need to chat with him about, because the pettiness will absolutely hinder his own healing), I do not want to be the cause of further hurt and pain by making a move on M. I do feel guilty about having these feelings at all, it almost feels like a base betrayal of R and his trust, more so since the breakup is still fresh.

I'm fully aware of the rule that one does not date one's buddy's ex, but I also do know, knowing M and the kind of person she is (with respect to her values, how she talks about her family, friends, passions, and life in general), that we could be happy (if at all we were to be together), even if only for a short while. However, coupled with the fact that M and I will both be leaving City Y permanently within the next few months to pursue our respective careers in very far apart places, I know full well that anything at all, if started, has a definite expiry date.

I'm not a big believer in fate, destiny, or whatever you want to call it, but I do believe in the law of attraction, and something, somehow, somewhere, some force, seems to keep pushing M and me closer together, not letting us just exist in each other's orbits but indeed making, and enabling us to be increasingly active parts of each other's lives. I don't know what the ideal end state between her and me is, it could be that we're being driven to be together, or simply just be very good friends, or be each other's "one who got away" type – and I say all this being well aware of her flaws, so, consciously not putting her on a pedestal and turning a simple crush into more than it actually is. I don't know. I simply don't know.

This of course is contingent on M feeling anything for me at all and that I'm still working on ascertaining. The chemistry is there, and I get the impression that she knows I'm (still) interested in her, and is being very nice about it by not saying anything about it – though we do continue to spend quite a bit of time together, both alone and with our friends and she's showing no signs of backing away, though I have also been careful to not over-reach, act too eager, come off as overly aggressive, drive her away and ruin our friendship. Another friend did catch me staring in M's direction for a bit at a party a few days ago but M wasn't really facing in my direction so she didn't see anything, which I guess doesn't create any problems, but I do have to be careful.

It feels instinctually wrong to even consider the prospect of making a move on M, or even telling her how I feel, all things considered, but I do recognise that I can't just shove my own feelings into a box, suppress them, and hope they go away (been there, done that, not fun). I'm also aware of the obligation I have, to myself and my own happiness, but somehow I find myself unable to square that with my obligation and desire to be there for R. He wants to hear nothing of M, nothing from her (even got pissy when she kept him in the loop about a medical condition that had an effect on their relationship) – and I think, justifiably so. He's hurt, he wants to heal, and out of sight and out of mind might well be the way to that healing. It's my job, one that I'm honoured to have and one that I hope to do well, to get down in the shit with him, stand shoulder to shoulder with him, and help him heal. I can call him out on his shit in the context of his healing and the fact that I do not tolerate disrespect towards any of my friends (which he well knows because he and I have talked about that many times) – but I have no idea how to have the conversation with him about the feelings I have for M. The cost however, of any of this, is that R (and a mutual friend of mine and R who is extremely protective of him – she has beef with M, and she and I have drifted apart lately, so less concerned about her) will more than likely never speak to me again, and that will be the end of our friendship.

I generally trust my instincts and my gut has yet to lead me astray, but in this case, my gut is telling me to do two things that I'm not sure I know how to square – nor my feelings for two people I care very deeply about. Would it be worth it to be quite sad and hurt myself after a brief stint of happiness, were anything at all to materialise? Is any of this risk, either way, worth it at all? If I could, I'd rather just be rid of these feelings, but I'm a practical man, I'm aware it's not that cut and dry.

Would appreciate any of your advice, and once again, thank you for your time, patience, attention, and kindness. Much love to you all, gentlemen.