There it is — he can absolutely be "bold and proactive", he just needs to carry that energy forward and internalize it.
Being in your own head about things is fine, to a point, but it's clear he's always been so preoccupied worrying about what she might feel or think about him, that he never trusted her to tell him, or to simply ask and 'check in'.
He's started voicing things aloud though, so hopefully that's an indication he's finding his confidence and will start making that change in a more foundational way.
Plus he scored a movie date, so that should make for an interesting chapter.