Oh shit. He said what his plan was to her in no uncertain terms...and then she immediately decided to get them back to their lives. We already knew it, but MC doesn't have to do well in anything to properly ask her out, he just needs to actually ask her. Of course, he doesn't realize that was the whole reason since he is denser than a neutron star.
Her rewinding to the first day, though, is there something important that happened that she wants to correct? I can't remember since it has been awhile since I read the prior chapters and I don't feel like going back lol.