To me, it becomes creepy when you consciously make an effort just to see (or catch a glimpse of) the other person.
btw,
pg 6: "Guess he overslept today"
pg 14: you made him way more creepier by making him say "maybe we should head there for shelter",
it should be just "shall I accompany you" or "escort you" or something like that,
"please don't hesitate to leave" --> "please don't hesitate to ask" or "please don't hold yourself back"