Should i make a move?

I saw a really talented local guitarist several months ago. I was so impressed by him, so I followed him on instagram. I then saw he was playing a solo set in my neighborhood, so I went to see him play and was really moved by his music. I reached out to him on instagram to see if he’d be interested in playing a show with me (I am also a musician) at a music venue in our city… so we had some contact online. A couple weeks ago, I saw him at a music venue and approached him to introduce myself in person. We had a really interesting conversation and I told him I loved his music. I just went to see him play again tonight and he initiated conversation with me, and smiled/ seemed happy to see me there. I also noticed him looking at me a few times once I took my seat. He seems really shy and a little nervous. I want to get to know him more, but I don’t know how to proceed without being too intrusive/ pushy. I want it to be organic and I want to see if he’s interested in me too. He might be someone who needs a little bit of a signal from me, but I also don’t want to be annoying if he doesn’t actually like me.