So -
Sugiyuki's pretty much likely the one who's making the Loop happen. Maybe not through exact intentional means, but whatever's causing it, is honoring her wishes specifically to never let "tomorrow" arrive.
To whatever end....well, that leads me to:
Asaki needs to actually ask her what her deal is. I'm actually amazed he's gone over 40 days now without trying to get more info out of her as to why she's so set on reliving the same day over and over.
He's so gung-ho on Yayoi-san and his crush on her that he's blinded to everything else. He's...I guess doing right by not forcing a kiss on Sugiyuki in order to get Tomorrow(Wednesday) to arrive, but ultimately he's gonna have to ask uncomfortable questions and force a conversation with her, at least.
If only to move the plot along, if nothing else.
Also - I'm betting next chapter (or within the next two chapters), he'll somehow get Wednesday to arrive, and Yayoi will push off their hang-out sesh again. It'll be much later on when he'll be able to get her to agree to a date, and only then will it come out that she's just not interested in him--and it'll likely be after he gets closer to Sugiuki, only to screw up and alienate/hurt her in some way and make the Looping go haywire.
That's my guess, anyhow, as far as plot developments. But in the meantime, Asaki needs to get his act together.
It's interesting, though, I'll give the author that. I very much look forward to learning more about Sugiuki's whole deal.
Thanks for the TL