How do you start/have a long conversation through text?

Anonymous
I won't be seeing my crush anytime soon and I want to talk to him once in a while. The problem is that I'm horrible at texting and starting a conversation. Even when I do start one, it'll end really quickly because I do not know how to continue a conversation or make it interesting.

It'll go something like:
Me: Heyy, have you heard this before? (sends a youtube link)
Crush: Oh. This is from that movie? Is this a fan made song? (yeah, he recommended a movie to me)
Me: Yeah. But it really looks like the characters are singing it.
Crush: Yes. How did they edit it?
Me: I'm not sure actually. But there are tons of edits like this.

Here's where the conversation ended. He never replied, but he saw the message. I really do not know how I can make the conversation more interesting and last longer.
How do you start/have a long conversation through text?
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