Crazy plotwist:
Daisuke become the protagonist of those mangas where he(or his consciousness) time travel back to his highschool years,and re-live all his experiences.
Several loops,too.
One for every girl.
https://mangadex.org/title/23e06c66-23d0-4343-a634-799d3e324222/shounen-chotto-sabotteko
This one is tricky.
The author also has a hentai,where it reuses de same characters,but the ages are reversed.
This:
https://mangadex.org/title/d1fa8ce7-ad9d-475d-9311-2a850b1f3336/sekai-wa-owattemo-ikirutte-tanoshii
BTW,you may wanna put your description on a spoiler.