Of course.

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His mom texted last night to lmk he dropped by for a surprise visit, gave me some brief updates. He called me this morning and we made plans to meet up in a couple hours - so, I'll get ready and drive to town and Hopefully we meet up as planned, catch up/hangout, probably go grab food, maybe go do some Christmas shopping somewhere. Time will tell.

Met up, out doing most of my Christmas shopping together now.

Spent over a day together, shopping, food, movie, errands etc. Good conversations about a bunch of stuff. Hopefully hear from him more frequently moving forward.

We spent another day together a couple days later. Mostly good positive stuff, no real conflict just real chats about things like communication & expectations do’s and don’ts for both of us on different topics - I’d label those convos as productive constructive criticism vs disagreements or anything like that, so good imo.

I was a bit concerned I may have pissed him off with something, but nah, got a phone call from him later that night and all is well really. He’s good at communicating fairly directly vs being quiet or shutting down or being passive aggressive etc which I appreciate so I can learn his style and be better myself.

Christmas dinner is at my twin brothers and his wife’s new condo this year, but this one wants me to come to his parents place. I said I’d come early (especially since we/I bought gifts for his parents) then go to dinner at my brothers. He said a couple times he wanted me to stay for dinner. At first I was like maybe for a light plate, then I’ll go join my fam dinner.. but then later he said he wanted me to stay for dinner because everyone else there (6 other ppl) all have someone to spend Christmas with and he didn’t wanna feel solo at the dinner table. Then said it wasn’t that big of deal if I couldn’t stay since we’re a new thing anyways. Knowing that, I told him since it’s important to him I’ll stay as long as I can and might even skip my family’s dinner and just head to my brothers after dinner. I’ll only leave earlier if my friend Greg is gonna make his way to my brothers for Christmas dinner like he came to my other brothers for Christmas dinner last year. (He has zero family here.)

He liked that I acknowledged that this is important to him and how he feels around his family. I get that on multiple fronts.. he’s the older sibling, his grandparents are visiting from Ontario, he’s trans And the black sheep of the family when it comes to.. lifestyle, so, I Get that it’s a feel good thing for him to be able to introduce me as his partner and feel a sense of normalcy, pride, belonging and so forth vs an outsider at the Christmas dinner table. And I certainly don’t want him to feel like I don’t want to be there or seen with him or anything like that! When I do dip out in the evening, I’ll be sure that ppl know I’m only leaving because this is very likely my own father’s last Christmas with us before his infinite journey through the ether to join all other ancestors on the other side.

^If anyone bothered to read this post, Note: It’s important to listen to your partner and learn and accept Why they want a certain thing or outcome and then to follow through and accommodate that Even/Especially If they say it’s “no big deal,” if you don’t -> that’s a clear sign that it’s a really big deal to them.

Well, that's sort of the end of that.

He called me this afternoon to talk and tell me that after some soul searching he doesn't want to further a relationship with me, or any cis-guy. He's learned he needs to be romantically involved with a cis-girl or similarly constructed trans-guy.

We both do genuinely care about each other and know that we will remain good friends, but we just won't be together.

I suppose you could say he was experimenting a little as he does like me and knows I care about him and treat him very well, so he wanted for it to be able to work out but knows he doesn't feel that way about me. Knowing this, his lack of contact was both being high af on drugs And not wanting to discuss this. I guess it took time for him to sort out his feelings and have the courage to have that conversation.

We discussed some intimate things respectfully & maturely. I don't think either of us have regrets of giving that a go. Sucks he didn't speak up earlier. Although I knew he was more into girls etc and knew I was more into him and he was into me - but it was Him that suggested fwb and then being exclusive with each other sooo it's a bit frustrating/disappointing.

My initial thought was nah I'm not gonna come to your fam's Christmas, it'll be awkward. But I called and left a message for him to call me back as he said I could still come, and maybe he wants me to - we are close friends. Just the initial sting of the convo I felt it would be awkward, but, I can be mature about our friendship and let him introduce me as a friend that's been instrumental in helping him sort his s**t out and hopefully get back to sobriety sooner rather than later.

If it's not meant to be, it's not meant to be - and I wouldn't want him to fake it or pretend like he wanted to be with me if he doesn't. That's not cool. I did tell him that the times we did hookup were as good as they were to me because I really care about him and it was meaningful sex vs. just hookups.

I suppose not seeing each other for several weeks at a time makes this easier on both of us, as we were drifting apart communication wise vs. growing closer together. I did have thoughts that this may be the case, but then spending a few days together and having relationship conversations I didn't really expect this.. but, it's still not shocking. Disappointing and heartbreaking, but I'm certainly not mad at him.

I suppose one lesson I've learned through all of this is that I can actually be open to the possibility of being in a relationship with the right person if it feels right & mutual for both of us vs. avoiding one entirely forever feeling like I shouldn't be in one. There's value to that for me. And there's value to him having learned he'd rather be single forever than date a cis-guy -> he is only 23 years old and going through a Lot with life, stress, hormones/trans issues etc so I can't expect him to have himself 100% figured out and not to "experiment," seeing if he'd be a dating match with a cis-guy.. and I told him I'm grateful to have been that guy to him.

He knows I still care about him and will help him out when and how I can in terms of life/sobriety/guidance etc, but that I might not make myself as available to him as if we were dating. He does owe me a bit of money, but knows I don't expect it repaid instantly and he can take whatever time he needs to repay it - it's not friends off, we're just not going to be a couple. We are still exchanging Christmas presents, and if he calls me back tonight or tmw I'll see how he wants to approach Christmas day/dinner, if he wants me there I'll attend and still take the bottle & chocolates for his parents.

I also told him I don't want him to be changing his mind about things every few weeks or whatever, as some things he's been a bit flakey/flip flopping on and this is a big one. If this is how he really truly feels and needs to be true to himself and not date me, then that decision has to be pretty damned final so we can both carry on with our lives as well as our friendship. He agreed, which is very mature of him, IMO.


So, yeah. Just had to put that out there to WP and get this stuff "off my mind and onto paper," so I can focus on completing my homework assignments before their midnight deadline. Thanks all whoever's reading this saga. I might still update this thread with critical things like if he achieves sobriety, stability, proper housing, skills training/employment etc - as he and I both know we want to be a part of each others lives, it's just not going to be in the partners capacity.

edit: He called me back just now. I'll still go to his fam's for Christmas earlier on before I go to my brothers. I figured it'd be mature of me to do so, to not avoid him, so that we can move forward as better friends vs. avoid each other or hold any sort of bad feelings etc. Just meet up, accept what is, deal with it, move forward and stay in each other's lives.

Thanks for keeping us updated.
Sorry things didn’t work out between the two of you.
Your good soul shines through.

Yeah, it sucks. This was the first time it was ~almost mutual and I thought Maybe it’ll work out so I’ll be open to it and agree to not sleeping with other ppl and taking things slow etc.

At 40 years old it’s growing increasingly difficult to believe I’ll ever really truly “click,” with someone and be in a committed relationship that we’re both mutually into. Granted, until this recent start to a relationship, I’ve mostly been closer to the idea save for a few intense prior crushes I’ve had.

I know, I’m 40, not dead. Most major life, career, business and financial successes happen after 40 anyways - so it’s possible that love could, too.

We’ll be friends for life that’s for sure, and I believe we’ll be better more trusting friends for having been intimate. He’ll know that my help, advice, guidance and so forth pertaining to his lifestyle improvements all come from a place of love. If that’s how we’re meant to be in each other’s lives, then so be it. Obvi I love him and want him to be happy - and if that’s by being romantically involved with a cis girl, so be it, live your truth and be happy little man.


I have other things to do in the meantime. Work/business, currently taking a course to get into different more lucrative work, need to re-commit to healthy diet and exercise. Want to get back to kiteboarding tonight the summer, motorcycling. Still might be taking on a 15yo type 1 diabetic Godson as a roommate if that situation that’s been ongoing for a year evolves into him exiting that home and being under my care. I have overdue taxes and invoicing and administrative life things to do sometime etc. Not exactly like I have nothing else to do in my life w/o having him as a partner - it just would have been the cherry on top if he was as into it as I was.

Blah blah blah, plenty of things don’t work out because something else is supposed to later. Maybe that’s a mutual partner, maybe it’s my time, energy & money going into other pursuits that having a partner would complicate. Even the new line of work I’m preparing to enter in film set construction comes with minimum 50 hour work weeks. It becomes almost all life consuming, but makes quicker progress towards financial goals than other jobs or sporadic contracting.

Everything happens for a reason.. it’s just that sometimes we don’t know what that reason is yet.

No call back last night or tdy yet - supposed to meet up and swing by his parents place for Christmas for a while before I go to my brothers place this eve. Time will tell if he calls.


On another note, as much as I obviously am attracted him as a person and would have liked for things to work out, I'm also quite realistic about the fact that I'm likely dodging an entire hailstorm of bullets by not being life partners with him.. I mean, he Does have a metric s**t tonne of issues. Things I would have accepted/tolerated/dealt with, but in the grand scheme of my life, it'll be a whole lot less work and energy to not have to deal with those things in such a personal capacity and only have to deal with them as lifelong friends vs. partners.

Sometimes things aren't meant to be and for good reason, even if it's initially heartbreaking. These things I know & realize.

edit: Not gonna kid myself tho, while I knew we'll remain friends 100%, I'd Also oblige to any sort of fwb moments he's ever down for. It's smokin' hot and we both enjoy it. I also have the capacity to do that thing and not expect that we're going to date or be together. Will communicate that to him for his knowledge, too, but won't press the issue. I'll leave that ball in his court.

edit: A few other things I've thought I wanna communicate to him, too, some feedback/criticisms that I know he'll accept well about his use of language towards me and him being the one to escalate relationship status things so it then was a bit of a shock to hear he's not feeling it. But maybe he needed to say those things out loud, words like "partner," to realize it didn't feel right for him ? Will talk.

Annnd he also needs to know I did my Christmas shopping during the time he referred to me as his partner and that I won't always be nearly this generous with him, but I'm not about to not give him gifts and be petty about things. Just the timing was.. inconvenient that way.

Sorry about that.

I sense, like you stated, that you “dodged a bullet.”

Yeah. But seeing through the bad and into the beautiful good, if he was as mutually into me I’d have taken those bullets. I know it’s wild, but lovey feelings make people so crazy s**t.

people can be so disappointing at times.

He called me a couple hours+ late and I altered my Christmas Day plans to zip downtown and collect him and make a stop or two along the way to making sure he gets to see his family for Christmas.

He’s at least appreciative of my kindness.

you deserve more.

Maybe. But I’m an idiot & like this one.

We discussed a lot of things, his trust issues, his perceptions of things.. (drug/mental health induced) and got to the root of his concerns, wants/needs etc. Some very mature adult conversation and he/we decided that he could date me under certain open relationship conditions that we both agreed to for each other.

So, now we’re back to being the beginning of a thing together, and he’s got plans for his next attempt at sobriety & stability on his terms in a way that works for him. I’m all for any method or process just so long as he’s trying and trying again until something sticks. Eventually he’ll get back on track and healthier again and he accepts that some
of his perceptions are influenced by his health/substance use and that I’m very patient and caring in dealing with it.

Some may say I might be better off solo and better off as just friends with him. Logic/rational thought may say that, too. But I *like* this beautiful soul too much not to try to make it work if it’s meant to work out. It’s an unlikely and unconventional relationship dynamic that’s for sure, but I just can’t ignore the magnetic attraction I have nor how magical it feels to have meaningful intimacy with this one.

Hopefully his various issues are merely temporary and his health rebounds fully.

i'm guessing he is quite the dish. that is yankee slang for really attractive.

Yes - inside and out, which is why I can tolerate & navigate his issues.

If we’re talking purely superficially/aesthetically.. also yes. Very cute, smokin’ trim body, various highly attractive trans masculine/androgynous features. Very unique but extremely appealing.

Personality, sense of humour, values and ideals to match. Many pros. The cons are hopefully mostly temporary and dealt with on a journey back to sobriety, healthy diet/water/sleep/exercise - all goals of his he’s working on & towards vs giving up.

He’s a beautiful person and I see all the good in him vs stopping at the current lifestyle issues and writing him off - which he acknowledges and appreciates my non judgemental/accepting nature about those things. Ideally we see him get back to sobriety, health, wellness, work and stable life bit by bit.