In addition to the active choices you make, your character's personality affects the "choices" made during the week interludes. (You'll notice stuff like "You kiss him in public" versus "You resist the urge to kiss him" depending on the MC's stats.)
You should make more "shy" choices at the beginning of the game, particularly when meeting new people, and that'll help you better handle these points.
Other that that, coming out to him early (either randomly meeting him outside Q&A or messaging him at the right time) will also help.