Amusing interaction, but this seemed a bit out of character, especially for Ruby. On the omake page, they look like they’re regretting some of their life choices.
Well, the artists made Ruby more of a agressive character in his view. I have read his doujins that are linked on his pixiv site https://www.pixiv.net/en/artworks/81209598 (most recent upload containing all parts of the You x Ruby series. Warning R18) and i have to say, she is far the opposite from being shy in the stories