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!