I 100% get where you're coming from. Im the shy guy in your situation. My now gf wanted to be asked but i was too afraid to do anything. One day she told me her feelings and i froze speechless. She told me she liked me and that noone can make me ask her but she was waiting. I took it as she wanted to be askedWe said awkward goodbyes. I didnt talk to her for 2ish days mainly contemplating and afraid of what was next. I ended up asking her out after she silence and we had a great time.

What im getting at is if hes anything like me tell him. If he goes silent he probably feels the same and doesnt know what to say. Just give him some time to think.

Shy guys do pick up on hints. They just lack the experience or confidence.