Understanding a shy guy?

In person he: tries to make me laugh, stares from afar but when close cannot make eye contact, red face when I sit near him
He is very shy, as am I. A loner type of guy.

After school ended, I got his number from a friend. I told him I had a crush on him and he didn't say anything, just that he thought my friend was joking about me liking him. We no longer see each other since we just graduated. I'm always the one initiating text. He replies quickly but most of his responses are one word. We never really get past small talk because I don't know how to keep a conversation with him going since he doesn't give me much to work with and doesn't ask me anything. The last message of our conversation two weeks ago ended with me asking him to send pictures from his trip. I never got pictures... I don't know if that's because he didn't actually go, doesn't want to send, or is waiting for me to ask him to send something.

I don't know what to do because I'm stuck between: he likes me and doesn't know how to express it/talk to me. Or just in general doesn't want anything to do with me. In person I really think the feeling is mutual.
I don't want to let go, since I really like him. But I don't know if it's my job to get him out of his shell. I'm barely even out of mine.
Also I'm 100% sure he is very introverted/socially anxious. that's why this whole situation is so hard for me to decipher.
Understanding a shy guy?
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