God, these three lovable idiots are me. They're me personified, and I love this bittersweetness of youthful love. I bet Oji-san will become one of the watchers, but will use his monthly meetups to further the romance eventually. It does seem like the logic is 100% manga logic though! If he only does it a few times a month- he was in the second chapter, now the fourth. And author-san is good about bringing back characters you think are just background characters and making them relevant later.
I just want them to at least exchange numbers before summer break!!