Wow, this was a banger of a chapter.
Takaya was kickass subbing in for an injured guitarist (the dude learned guitar AND got good enough at it just to impress Kana, respect), and him copying the other dude's line was funny. They actually managed to successfully wingman their friends together! Too bad that wasn't what was keeping both looping.
Also too bad they also don't have time to do that every loop, so this is only one time where Kita and Risa get together successfully. Unless memories for other people who interact with them somehow start bleeding through loops, I think we can assume Kita will fail every loop after this and he will not get together with Risa. Shame, I love side ships.