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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.

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thank you, this and the video walkthrough by Chloe really helped.. Jake is so adorable.. all of the stories were very well written... wold have kind of been nice if you had a friends only track with Nikhil (like he knows you have a crush on him and you try things but it doesnt work out) or a romance with Nate but I know that would have been a lot and the game itself is very well done so not criticizing in the least... cant wait for the Zags sequel... keep up the great work!!