Just read this today, and why are you so insistent on translating Outa as Sakurata
The furigana clearly showed that it is pronounced Outa
Tsubaki never once said Sakurata
also page 9, remove the "you," from "I've always like you, Outa-kun"
And Tubaki's name is also wrong, what the heck
It's Aga Tsubaki and Tsurugi Outa
Atleast this is a new Experience.
A Mc Being a Wingman is definitely Different in 99.99% Manga's out there. Damn bro It makes me Shiver of how painful bro is going on through.
What if he does nothing and lets the flow go on, like letting the girl confess to the boy on her own way, not by forcing/pushing it. Maybe that's why it's always in the loop, or maybe he needs to be true to his feelings, like confessing to the girl even tho he will be rejected. I feel like the loop plot is to deny the MC to move on, and it's kinda brutal...