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.

Ask him open ended questions about what he likes or finds interesting. Ask him about times when he was afraid for his life or the most memorable vacation he’s been on. Ask him about his goals or aspirations, embarrassing or funny stories, where he’d most like to travel, etc. Conversation flows more naturally when people are talking about something they’re excited about and you might learn more about him when he describes his past or feelings or wishes. You can use the info you learn to ask follow-up questions. Just make sure to actively listen and let him talk. Don’t just be thinking of what you want to say next. Maybe he’s afraid to open up to you or look dumb. Show him that you can be vulnerable and share a funny embarrassing thing that happened to you.

Most people have encouraged you to be direct, and they are right in that it will very quickly get you a yes no answer. And also that it’s more effective on men.

But it’s equally true that if someone isn’t expecting that at all, a confession can surprise and stress them, as they struggle to put their feelings towards you together and decide on a future right in that moment.

And that can sometimes lead to rejection when it might not have occurred had the way been paved a bit more gradually.

To get specific, that involves doing things with just the two of you. But it also usually involves doing a shared interest, which you’ve said you don’t have.

So if you’re serious, I would suggest you think about what you know of his interests, and seeing if there’s anything you’d potentially like to know more about/get involved in.

Then say something like “hey I’ve started getting into __ a little bit, and I know you’ve been into that for a while, do you know of any __ happening soon I could go to?”

If he has any interest in you at all and is not completely dense, he will usually mention something, and if he does he’ll possibly invite you. Even if it’s like “don’t know of anything now but that sounds fun”, that is also an invitation for you to look up and propose events.

Once you’re at __ together, as the “expert” in the topic he’ll naturally take on more of the “host” role, which will get him talking. If he stops, unfortunately it is usually the woman that has to “go fishing” for topics, since men are not very good at it. Luckily being at __, which you’re not familiar, with means your questions will be real and natural.

And then there is the simple fact that if a man said “I’m cold” and then leaned against a women, he would be thought as creepy, pushy, or presumptuous, but if a woman does it, it’s sweet and endearing even if the man doesn’t like them romantically, because it shows you feel safe with him.

But sometimes, a man doesn’t know how he feels until he’s forced to notice. That will get him to notice. And then he’ll decide, and since men are not very good about hiding their emotions, as they’ve never been forced to, you’ll almost certainly know his decision by how he behaves toward you after that.

And if you think the answers yes, it’s then when you’d be direct. Of course, if you’ve dropped enough hints, maybe you won’t have to.

Your and his age are gonna be major variables here. Conversations and relationships work very differently at different life stages.

You sound like you’re maybe a teenager? Try asking interesting questions that require some thought to answer, but still leave room for your friend to give an easy thoughtless answer if they want to. Where do you think we’ll be in X years? What’s something you thought you wanted but as you’ve gotten okay have realised you actually don’t? What do you think we do now thar future generations will think is crazy? Listen to his answers and ask followup questions.

Personally, I’ve always been most impressed by directness, honesty, intelligence and courage.

You could ask:

1. What’s your best quality?
2. What’s your worst quality?
3. What does “home” mean to you?
4. What’s your favorite childhood memory?
5. Who are your role models?
6. What is your relationship with your like?
7. What is your idea of happiness?
8. Where do you see yourself five years from now?
9. What goal are you working toward right now?
10. What’s the biggest challenge you’re facing right now?
11. What does retirement look like to you?
12. What’s a skill or quality you would like to develop in yourself?
13. Have you ever experienced a life-altering moment that changed your perspective?
14. What do you consider your biggest accomplishment so far?
15. What’s the most difficult thing you’ve ever been through?
16. How do you cope when you’re upset or stressed out?
17. What are you grateful for?
18. What’s the best piece of advice you’ve ever received?
19. What’s your worst habit?
20. If you could change one thing about yourself, what would it be?

Also is kinda tricky; on one hand you could try to find out what hobbies he likes and do them together somehow. But if you do too forceful it might be too much…

So what have you done so far?

To echo what a lot of people are saying, just go for it with confidence (which is easier said than done, I know.) “Hey, I think we would be a good couple and I was wondering if you wanted to go out sometimes.” And if they no with same confidence (or fake it) “I’m so sorry, i must have misread the situation. Don’t worry, you don’t have have to be awkward around me.”. And that’ll take the pressure off of both of you so it’s not weird

You could try asking some deep questions, see what comes out of that.

I’ll help with the deep conversation part. All conversations can go deep, if you keep questioning them.

It’s hot out today. -is it getting hotter every year? Seems like it. I think it’s global warming. -what do you think the solutions are?

I think Gary is cool. -what do you like about him? He’s got a sweet mustache -have you always liked mustaches? My uncle had a mustache, he used to takes us to cool places when we were kids. -would you say your uncle had a big impact on your life?

The point is, if you keep inquiring a step deeper, the conversation inevitably becomes deep. Good luck, and have fun.