Dear Autumn,
By all means follow your instinct, especially if you feel, as you mentioned before that the "man should be doing the chasing"
You are right, some years ago, he surely remembers how you feel about him, and if he is shy, knowing this should give him confidence shouldn't it?
All the best.
Dominiquethe Hermit is a man of wisdom and patience. However, do you see how your last spread is going up towards le Jugement which is when things are revealed...
How long will it take? that is another question... but you do not seem to be in a hurry.
Since you have that strong connection and precious friendship, have you tried to ask him how he sees his future, what he wants in his life?... you know, general talking as friends do... just so you could get some hints and see if you are in the picture... without being too pushy.
Since you expressed your feelings