Okay, fifty year old asshole here. I’ve danced the dance more than a few times.

Don’t waste time fucking around. You have the feeling, you be up front, honest, and let whatever happens happen.

A real friend? Trying to go romantic and failing won’t change a thing long term. A real friendship is too deep to destroy by just not working romantically. And if it isn’t that deep a friendship? Then something would have ended it eventually.

Now, if things don’t work, but only one of you thinks that, it can take time and work to move past, but it will if the friendship was real in the first place because you’ll value each other more than the failure can break.

You also have to be prepared to hear a no, and then learn to move past the no. If you can’t, then chances are it wasn’t that good a friendship to begin with.

There’s going to be nerves, but you just open up, let it go, and let the other person respond. Don’t do any big gestures, no movie crap. Just be the person you are and talk about it.

Me? Once I got past the whole fear of rejection thing, it was always easy to just say “hey, we’re pretty close, and I’m feeling some extra love here, beyond the friendship part of things. It seems that’s reciprocated, so how about we try this? Let’s do a formal date and see if that gives us a jumping off point.”

The conversation goes from there to whatever the next thing is. Sometimes it’s a no, and solutions it’s a yes and things don’t work. But sometimes it’s a yes, and things do work.

Right now, me and my wife (that started as friends, and didn’t even realize we were moving into romance until I told her I loved her and things moved kinda on their own) have occasional dinners with three of my exes that are still good friends. And I’m still in contact with others that aren’t close enough location wise to have many visits.

Tbh, the only exes that I’m either not still friends with, or wouldn’t be if we were in the same location, were ones that didn’t start as friends.

Seriously, the next time y’all are going to be together, when there’s a moment that the feeling it’s going somewhere, say something.

Shoot your shot, player.

Don’t go crazy or over the top, don’t overdo it, but just say it. If they’re a good friend they won’t be scared away. If they’re like you that way you’ll both be happier.

Don’t overthink it, ask them if they’d ever like to hang out or do something more like a date.

Ballsy, direct, badass. That can be you.

Dating is awkward but life gets a lot better once you get more comfortable with it. Everyone is a dating idiot until they’re not, there’s a good chance your friend is still in the idiot stage and maybe hell be over the moon that you helped push through it.

Touch his butt.

The nuerodivergent part suggests you’re going to just need to be direct.

“I really enjoy our friendship, it’s important to me. I want to make sure we keep that friendship regardless, but I’ve also realized I might be developing more romantic feelings for you that I’d like to explore together - maybe you’ve had thoughts/feelings like that about me before? If not, that’s cool, I just feel better having said it to you so it’s out of my head :) but yeah, I like you and I’d like us to get dinner on an actual date date sometime and see how we both feel. What do you think?”

Or there’s always Margaret Cho’s technique…

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.