Here is a place for the things I didn't and or don't say out loud. These are my own thoughts and feelings. Thoughts of the past, thoughts of the present, and possibly what I'd like to do in the future. Thoughts of those simply passing by, those in my class, my family, of my friends, and at times myself.
I’d say be straight forward. See what he likes, and invite him to a date to something relevant with that. You can even be straight forward about acknowledging his nervousness. Let his feelings be recognized. That’s generally a compassionate and kind way to connect with people. And maybe after confirming his feelings of liking you, let him know that it’s mutual. Hope that helps :]
She deserves better, you say. I say: You’re a goddamn coward. What she deserves is an actual person she can connect with. She deserves you, or me or the entire world; she deserves someone achingly real and honest. She deserves a human being equally raw to pursue her and love her and, perhaps, destroy her emotionally, but she deserves all that as well. She doesn’t deserve anyone’s sugary fairytale. She deserves to float freely, with you, or me, or the world, into the very depths of her own psychosynthesis. She deserves to explore the meaning of the word "intimacy", with someone beside her that will care regardless. She fucking deserves all of it. So, pluck up the courage and be with her or leave her in peace but don’t you dare "sell" her your own "inadequacy" as a lie so that, again, you manage to comfort your conscience and eventually come to feel that you love her exactly because you’re letting her go. Because, darling, that’s bullshit. That’s only your own little self-created lie laying behind a much bigger lie; it’s not even properly concealed within itself, you fucking idiot.
What matters most is figuring out each other’s boundaries, desires, and needs. You don’t have to be aggressive, but you can be assertive about how you want to be treated. Let him know straight up what you want—such as you preferring that he sets up dates more often, but don’t put too much expectations over the details of how your needs can get met. Also, why not address to him that you’re concerned if you’re coming on too strong to him and hear out his opinion? Were it me, I’d think you were being thoughtful of me and honest about yourself .
Also recognize that shy guys typically have a slower pace over disclosing themselves and over the rate/degree of affection they express. You can show that you respect his pace of intimacy by verbally letting him know that you’re patient.
Hope my response helps. If it hasn’t, c’est la vie. :]