@DigiTrash Characters here always talking quite philosophically and vague so the real meaning are always left to readers interpretation most of the time.
My guess about Hayama-Hachiman talk (w/o reading the LN):
Hayama noticed that Iroha doesn't really like him and like some else (Feels like Hayama implying it's Hachiman and Hachiman should knows it).
Iroha-Hachiman:
I'm guessing her banters with Hachiman is her way to keep the status quo with him and also kinds of rejecting her own feeling or she herself didn't notice her feelings to Hachiman but everything she does suggest otherwise.
I hope I'm not reading too much but I like Iroha more than Yui/Yukino so maybe my understanding was bias.
@Sunoftheeast If you watch the anime, the gap are all covered in season 2, chapter 60 continues where it left off.
But it still worth reading the manga because I notice some details are left out but some scene are really good in anime though.