Making aspie/aspie conversation

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I'm seeing a fellow with Asperger's and it's so wonderful because we are so often on the same page with things and I don't have to explain my ways to him like I do NTs and I feel very very comfortable with him. I'm aware of it and he's mentioned it, that we don't actually know each other all that well, for what it's worth.

The only way I really know how to make conversation with anyone is by asking questions. Usually that works with people because I can ask a question and then the other person starts talking and enjoys talking about themselves enough to keep going and shifting from topic to topic by their own doing. I "make conversation" by prompting chatty-Kathy's, basically. But of course he's not like that, he has pretty direct, simple answers to my questions. I could keep asking him questions on and on, but I get nervous to seem like an interrogator. He doesn't usually toss questions back my way, like I sometimes expect he would, but I don't believe it's because he's disinterested, I just don't think it occurs to him that he could do it. I honestly think I know a good bit more about him then he does me. I have no problem with the idea of opening up to him, but I'm not going to just throw my life story at him if he doesn't want to hear it. Usually we end up sitting in silence, or don't have terribly substantial conversations, which is okay, but I would like to start really talking with him.

What should I do? Do I just talk about myself even if he doesn't really prompt it? I think I tend to be pretty direct with my responses too, I mean why go on and on about yourself? I guess I just always think it's a bit self interested when people can just endlessly talk about themselves. That's not like what I want from him, just a step towards deeper conversation. And he says he wants to know me better, but how do I establish that when he never asks me things?

My inability to interact socially is very frustrating right now.

do talk about yourself for a bit but find out what he likes and then ask leading questions.

I've tried asking leading questions, but it's like he doesn't notice the leading nature of them. Unless I'm asking the wrong things. Any examples?

if he just happens to mention one of his interests to you, as him questions about that, a tried and true method of getting somebody to talk about something at least.

If the silence between you is comfortable don't worry about conversation. It'll either happen naturally, or you'll remain comfortable.

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Could you talk about things that aren't direct questions about each other (or talking about yourself), but discovering what you each think or feel about things? Like, talk about a particular topic of interest without the purpose being getting to know each other. The purpose is instead to share ideas, debate, etc. but by doing this you will learn about each other anyway...and often some pretty interesting stuff.

These are the sorts of conversations I have more often with like-minded people, and they can carry on for ages if the topic is interesting/controversial/open-ended enough.

everybody has an opinion about something under the sun, find out what his opinions are.

I'd recommend talking about your special interests to each other. You might both worry that the other has no interest in your particular field of interest, but understanding the passion and appeal you both feel is a very good way of getting to know one another. Talking about yourself is never going to be easy, but talking about what you know is a good workaround, and even if you have no interest in the subject the connection and interaction between you both feels so nice that it doesn't matter.

This is exactly why I am doubting whether I can fall in love with the aspie boy I am dating right now.
Our conversations are sometimes so unfulfilling to me.

The other day I walked into his room while we hadn't seen eachother for a week and he went to hungary, and he was just watching tv. He didn't immediately shift his focus towards me. Just weird, and cold. I wanna talk about experiences, about me, about you.

Good to see I'm not the only one...

There's this girl who seems very much like an Aspie. I'm not sure if she is actually an Aspie or just very shy, and we're not dating (yet?), but trying to talk to her has been very frustrating for the reasons you describe.

In the hope that I can help here: First, talk about yourself even if he isn't asking. Just make sure he doesn't get bored. Second, look for a common interest, and when awkward silence occurs, discuss that. In my case, I've only ever had a fluent conversation with her when I had prepared a factual topic.