I (27NB) met a guy (~30M) on an app about 7 months ago, we chatted for a short while and then met up for coffee, to feel if there was chemistry.

There both was and wasn't for me. On one hand, he was very sweet, physically my type, a good communicator, and considerate and in the know-how about me being trans. On the other hand, I got the feeling that he had never really flown the nest so to speak; he had never lived anywhere but his parents' house, never had a job, and said he didn't really have any friends. Maybe the last two are more open to interpretation - when he said job maybe he meant a "proper job" but has had other employment, or that he has been unable to work due to illness, and my experience is that some people say they have no friends when they actually do (for some reason). But it can also be just that: never had a job, don't have any friends.

I thought about it and decided, despite his many fine qualities, that what I view as an overall inexperience in life was too much of a turn off for me. I messaged him saying I wasn't interested in him in that way. He took it really well and we haven't been in touch since.

Lately I've found myself wondering if I made the right choice with him. A part of me wants to reach out and ask if he's interested in meeting up again. Maybe just to hang out, maybe with the explicit purpose of hooking up. I felt pretty shallow for rejecting him back then, and I'm curious to see if I could look past the life inexperience and see a more fully fledged person than I imagined him to be.

But I also really don't want to meet up only to change my mind again. That seeing him again will remind me of my original reasons not to pursue him, and he would be rejected again.

Full disclosure, I haven't had that much luck finding other people in my area, at least people who are interested in having a conversation with me and not JUST fucking (not even kissing, it's too gay for some of these guys apparently). I'm totally fine with having a FWB, in fact I would prefer it over something romantic right now, but I don't want to completely skip the "friends" part of friends with benefits either, and one night stands feel pretty unfullfilling to me. Also finding what I'm looking for as a gender non conforming person is pretty hard in my area, a person basically has to be bi in order to find all of me attractive. Maybe my bad luck is making me reconsider, but is that inherently a bad thing?

I guess what I want to do here is in part to get it off my chest, in part to ask what you think is a good course of action here? Am I being really dumb for considering to reach out to him? Or do you think there could be something there? If anyone can relate to his situation I would find that extra useful.

TL;DR: Met a guy a while back but wasn't interested at the time because I viewed him as inexperienced in life, now I'm wondering if I was too quick to reject him. I want to get in touch, but I also don't want to hurt his feelings by potentially rejecting him again.