Manga Shounen, Chotto Sabotteko?

Ninomiya Yuusuke is a serious student who’s always focused on his studies, even on his way to school. Along the way though, he always encounters this laid back office lady named Kirigiri Saori who is constantly encouraging him to skip school and hang out with her! Although reluctant at first, Yuusuke begins to open up to this woman who despite being the complete opposite of him, he gradually learns from her the importance of taking breaks.