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.

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.

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.

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.

Would you say what you’re seeking is “more intimacy,” up to, potentially, the most possible intimacy?

I would suggest looking at his different interests and getting curious. If you’re interested in the guy, it should be pretty easy to find reasons why this film or that game are endearingly-this-or-that in a way that makes you like and respect him even more.

Then, you bond over it; by trusting his taste (intimacy) enough to check out that show or whatever interest, you now have an opportunity to get deep (intimacy) into what you each individually felt (intimacy) about it, and maybe you felt something in common. That’s some foundation for intimacy.

This is a good one. Maybe there isn’t a way? Maybe it’s not the right time?

My wife and I are two people with different interests who just happen like each other and have a family together-we often comment on how if we had met any earlier in our lives we would definitely not like each other.

For the most part of our marriage I worked alot. But we were always together when we could be.

Currently this is the most we have been together (last 6yrs of 25) because we now work together in our own place, and the kids have grown and moved out…and we still like each other!

Love is not a question if you like each other, and you can be two people who are together. You don’t have to have deep meaningful conversations to make a good relationship, my partner is a empathetic, thoughtful and philosophical person and I tend to go for the fart jokes.

But we get each other. Do you guys get each other then you are together?

Hopefully this rambling statement makes sense, from a different perspective. I’m tired and am having my first cup of coffee.

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?

I already responded somewhere else, but I have more response that doesn’t make sense in that context.

First, about deepening conversation. I don’t know about this guy, so I’ll talk about myself. I have things I’m interested in, let’s call them “interests”, and I like to talk about them. And the only thing that stops me from talking about them constantly to everyone is the social understanding that they don’t want to hear about my interests.

So all it takes to have me talk about stuff is enough questions to demonstrate you really want to know.

“What do you like about blah blah blah?” will probably get a short answer because he’s used to people not really wanting to know more, so he’s giving the smallest answer that answers the question. But then, you ask a question about his answer. “Huh, how is that different than blah blah?”

Now maybe longer answer, you listen and ask based on that, and if you can manage it you could also circle back to a previous answer to connect some dots. That’s now a discussion! Now, of course, you do have to listen. Unsure if that’s a skill of yours or not.

As for the asking out, I think you should do it. But if you don’t trust yourself to deliver the speech live, you could write it down / print it out. Just make sure it contains escape hatches for him that assure him it’s okay if he doesn’t share your feelings, and that he can just tell you if that’s the case, and probably ends by saying he doesn’t need to necessarily give you an answer now and you’re just happy you could get it off your chest. I think going for something casual is better than something heartfelt and romantic, but I don’t know the two of you. The most important thing is that he knows, and the second most important thing is that you don’t want it to wreck things if feelings aren’t mutual.

And if you don’t want to awkwardly read it, you could just hand it to him and let him read it at his own pace. This lets you watch his face while reading, if he makes facial expressions and if you can read them.

I would recommend against an email or a text, though. It feels like, from the bits of your personality I’ve picked up here, the time between when you send it to whenever he responds is going to be absolute torture for you. Whereas he might just be busy and not have even seen it yet, you’ll already be inventing bad scenarios and deciding which new city you should move to since you obviously can’t stay here, etc, etc 😉

So probably best to deliver it in person, maybe at the end of a hangout, so you can be sure he received it and read it. And I know you may be scared, but don’t tell him to read it after you’re gone, because that’s now email territory where you can’t ever know if he’s read it yet! Just have him read it, assure him it’s okay if he doesn’t agree, and let him respond. And even if he doesn’t have an answer now, you know it’s done.

Good luck!

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 show him this post. Communication often comes down to just being straight forward with your message and allowing people to respond rather than imagining it.

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