I never had much luck dating, tried shooting my shot with a handful of female friends I thought I was getting vibes from, never even got a first date, but stayed friends with them.
The only 2 times I successfully ended up dating someone, the girl took the initiative and kissed me first.
First one was someone I’d just recently met, didn’t really pick up on any vibes, maybe she was putting out a ton of them and I was too much of a dumbass to pick up on them, I just thought she seemed cool and wanted to hang out with her, didn’t really have any romantic intentions in mind. Then she kissed me, I kind of had to quickly rewire my brain and I decided “ok, let’s see where this goes.” Didn’t work out long term, but we had some fun for a while. I did not stay friends with her, she got kind of weird towards the end, and I found out years later that she was very likely cheating on me towards the end, I wasn’t my best self at the time either but I wasn’t a cheater just a stupid teenager, I tried to leave the door open to remain friends but she wasn’t having any of it.
The second time I’d been friends with her for a good long while, again, no romantic intentions on my part, she was cool, we hung out mostly with other friends, sometimes not. She kissed me as we were both leaving a party at the same time getting into our own cars. Really short circuited my brain a little and could not make sense of it. Kind of had to take a day to process it and talk to her to confirm that we were gonna try it out and see where it went. She’d apparently been laying on the flirting extra heavy and I picked up on absolutely none of it. I ended up marrying her, coming up on 6 years married and close to a decade together.
For a 3rd data point, there was a girl I really liked in high school. I’m pretty sure she was flirting with me pretty hard, and several other people even told me in pretty straightforward terms that she liked me. Never quite got out of my own head enough to make a move beyond some clumsy, mostly-joking-but-not-really flirting. I think I was kind of waiting for her to make it clear to me what she wanted in an unambiguous way, and she never quite did it in a way my brain interpreted as an “all systems go” signal.
For some context, the first time I was about 18 or 19 years old, and I started dating my wife in my mid 20s, my failed attempts were all scattered around my early 20s. I’m probably a little neurodivergent in some way, some very mild degree of autism if I had to guess, and depending on who you ask I’m either a shy extrovert or an unusually outgoing introvert (the bit in Clerks about Randall hating people but loving gatherings resonates with me.)
I think the takeaway here is to go for it and don’t beat around the bush. Keep an open mind that he may not be into you that way, but that means he doesn’t want to lose your friendship either. If it’s going to happen, one of you needs to make a move, and there’s a chance that he’s just as stupid as I am and hasn’t even really considered you romantically but if you force his hand he may go “oh shit, yeah, that sounds like a great idea, why didn’t I think of that”
And even if stuff does implode, it doesn’t work out, and you don’t manage to stay friends, it’s probably better than spending the rest of your life wondering about what could have been. I love my wife, wouldn’t trade her for the world, and I’m confident that there’s no one in the world who would be a better match for me, but I do wonder sometimes what sort of fun I could have had with my high school crush, even if it wouldn’t have gone anywhere long-term. A couple weeks, months, or years of fun times would have been worth it. With the other girl I dated, even though things didn’t work out, and I think we mutually dislike each other now, I still think fondly of the times we had together regardless of the unpleasantness that came after, if I got stuck in a time loop and ended up back then, I’d still date her even knowing it wasn’t going anywhere.
Unfortunately I have no particular tips for improving conversation. Somehow I seem to do alright, but I couldn’t, for the life of me, explain how I do it.