why

I said: It's spring break. Do you have more free time? I'd like to see you again. Tuesday? Movie and dinner?

I meant: I'm beginning to like you more than I have before, and think I'd like to be better friends. Also I'd like to start kissing you.

And I trusted in standard social expectations to translate what I said into what I meant. This is what is generally advised. Because saying too much, too fast, is bad. Because elegant communication is subtle. But here's the thing: it never really works. He didn't translate. We watched a movie. And I drove him home.

I said: You seem weirded out. I'm sorry.

He said: I'm just tired.

I said: I like you. I enjoy your company. If you're ever not weirded out and tired, I'd like to see you again.

I meant: I'm beginning to like you more than I have before, and think I'd like to be better friends. Also I'd like to start kissing you.

It didn't work before. Why should I think it's working now? How can he communicate to me whether he's

a) not interested in anything different than what we've been up until now
b) interested in being better friends but not attracted
c) interested in being better friends, and not sure about anything more

if he doesn't know what I want? And even if he does know, how can I know what he's saying about it if I don't know that he knows? Do you see? My actions are going to depend on which of those things is true. If I guess wrong, it's bad for both of us.

How can he answer a question I don't ask? How can I understand his answer to a question I didn't ask? If I let him guess what I mean, and then I guess what he means in response to what I think he thinks I meant, how is this ever going to resolve itself? And why is this a good idea?

I want to tell him. In direct language. In writing, so he can take time between what I say and what he wants to say, without any pressure, or eye contact, or awkwardness. And I don't understand why I'm not supposed to do this. Why everyone tells me not to. I would want to know. Why wouldn't you?