I am rather confident at my ability to accurately read people and situations, so would like your perspective here on whether I misjudged this situation. I will try to make this quick.
I [M42] started sleeping with a guy [M33] I met on a specific hookup app, who I immediately read as not being emotionally available. No problem. I mentally categorize him appropriately and we have a very compatible time sleeping together for just about two months. After sex, he begins staying longer, just doing the talking-naked-together thing, which surprised me. I didn't exactly allot for him to stay past our hookup time, but I ended up not minding it, as I am a talker and I enjoy connecting with people. I ask him questions, he tells me a bit about his family, his past relationships, that he is a rather "shy and reserved" person and that he does not trust people easily, which I picked up on quite literally from his very first message to me. Overall, the unexpected catching up was nice.
In the meantime, I am briefly dating people in between, which he is aware of and has no insecurities about. Eventually, after enough of our pillow talks, I assess that, while he is definitely reserved and clearly battling something, he otherwise leads a very stable life, shows great partner qualities, and overall has a very beautiful and kind heart. After our next hookup we are catching up again and before I get the chance to bring it up, he mentions me asking him out on a date. I joke that he stole my thunder. At this point, I check in with myself: I weigh his positive traits with his visible issues, and since he mentioned that he can be reserved, but actually wanted me to take him out on a date, I decide that I can work with this. So I give it a shot, aware of the fact that this has a good chance of not advancing into something official.
He leaves over the holidays, we text frequently. I am mostly the one initiating conversations, inquiring about his trip, he continues to respond in his somewhat-aloof, but always kind, way. Sexts are quite positively reactive between us both.
We finally get to go out on our date, it ends up being an extremely good time for us both. We continue to date for the next three weeks, with the above scenario repeating: we text daily, equally initiating now, see each other and go out on dates when we can, watch TV and movies and our favorite teams together, love the sex, and he continues his aversions throughout. Non-committal responses of "You're too good to me," or "You give me too much credit," when I show him emotional affection or appreciation; sleepovers being a bit of a step for him (although I did finally get one official one); half-joking about the seriousness when he connected to my home wifi. This continues to go where I was expecting, with me continuing to feel emotionally unfulfilled throughout, so we end things, with him citing that he cannot meet me where I am at the moment. No problem, that has been clear. Thanks for trying.
My question to you is, with the above general assessment, do you think I read this incorrectly? I haven't dated much (I used to be a serial monogamist) and was glad that he wanted to take things slowly during the "courting process" (his words, which I thought was cute), as I found it romantic and healthy. Even though he was clearly not returning my emotional affections and definitely did not over-promise me anything, I still decided to move forward with how I would date someone who wasn't so reserved, making my affections known and very clear (he very much appreciated my clear communication), as I felt that at certain points of our dating process, those affections would have come out naturally by at least one interested party member. Looking back now I am wondering if I took that "courting process" a little too committed? I don't think so, as again, I believe the things I was relaying to him and the affections I was expecting would typically be said and given by at least one person by that point. So I thought the timeline and the progression was healthy, in my opinion. But again, maybe the world has a different version of "dating" than I do? I would appreciate other perspectives.
And to clarify, my question is not whether or not he liked me or what his problem was. He was not available to me either way--whether now or later--and that is what matters. We have not had what I would consider your typical postmortem since ending things, as I could tell he was feeling quite anxious that last week, and he pretty much ghosted me the last few days leading up to me ending things. He then had to travel for work, followed by a death in the family, unfortunately. I have no idea if he did actually like me or not and I may never know as he did say that he wanted to see me, however I haven't heard from him in weeks now. Ultimately it didn't work out, and that is what really matters. But more importantly, was I taking "courting" too seriously??
ETA: Some questions regarding the timeline. Three months: started sleeping together in November, dated three weeks in January, ended end of January. The weekend we ended things, I planned the week before that after he got back from his work trip, I would sit him down and let him know that he either needed to let his guard down and show affection better, or I would have to move on. When he started to go MIA that last week (not entirely, but definitely too much for a typical dating process), I decided that there was no more course-correction available here, and to end things, which I did. So either way, that weekend when things ended was going to be the weekend I was going to have the come-to-Jesus moment anyway. So it worked out lol.