Dating in the world of Okamisan hasn't exactly been out there, though you know that Ryoshi really wants to get closer to Ryoko. He gets his chance when a double date is organized after a different request comes in. That request is amusing as second year student Jizou has found that someone has been coming into his place, cleaning it and making him meals and generally helping him out. He wanted to know who it was so he had the club figure it out by installing cameras through which he learned it was being done by another second year student named Ami. She's a very cute if shy girl and when Jizou gets it all figured out, he insists in his very deadpan and reserved manner that he'd like to pay her back by taking her out. And that gets Ryoko and Ryoshi caught up in it by double dating with Ringo providing help to Ryoko through an earbud. The pair are quite cute together since Ryoko wants so little to do with this. But even when it goes awkwardly on their part, it inspires Jizou to be more forthright.
Unfortunately, the show takes a turn for the worse just before the second half where Ryoko gets a blow to the head from a shallow pond incident and loses her memory, causing her to not know who Ryoshi is. She goes back to a previous part in her life when she was a thirteen year old middle school student, and that gets a very awkward yet surprisingly endearing moment where she referes to Ryoshi as an older brother of sorts since she thinks of him as several years old. Ryoko in this form is very shy but happy in a way where she has what could be categorized as the epitome of moe-ness. She comes across as very fragile and weak, even if she is smiling all the time and full of happiness.
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