User blog comment:Takashichea/Weekly Sket Dance: Ep. 77 - The Campus SKET (Then)/@comment-139.228.119.32-20130428140317/@comment-4800771-20130428164944

Bossun never shared his feelings with Himeko. He treats her as a friend, but he does demonstrate jealously. See his relationship with Himeko on Bossun's wiki page. I don't read it because I'm not far ahead in the manga.

(episode 77 talk since I believe the manga's outcome is different)

Regarding Saaya, Bossun did not reciprocate his feelings for Saaya who confessed to him. He apologizes and explains that he did not see her that way and welcomes her to visit the Sket Dan clubroom. When Saaya meets up with Himeko, Saaya hints to Himeko that Bossun is a little kid. This implied that Saaya has not given up on Bossun. Not sure about how Himeko feels about Saaya and Bossun.