I was actually replaying parts of Kurugaya’s route the past two days (Mio and Rin’s routes aren’t holding my attention very well) and towards the end of the route when Riki starts realizing it is a dream and tries to stay up until June 21st to force the loop forward, he eats one of two instant noodle packages before falling asleep right after midnight. When he wakes up, the other pack of noodles is still gone, and he states the world is “imperfect.” You also see this when even though it is technically June 20th, what Riki says to Masato, Kyouske, etc. will either give him the “canned” response (if he mentions he’s going to see Kurugaya and they are surprised) or if he tells them to leave him alone, which they do without questioning it. It is a dream world of many constants and slight variations, all centered around what Riki does or doesn’t do or say.
The reason I went back was because I wasn’t quite clear on when the “loop” begins; Kurugaya/Riki imply it started after Riki realizes he loved her. However, when Riki is sick and she visits him, she pauses when Riki tells her it is partially her fault, and she appears momentarily confused but rolls past it without him noticing, which can possibly mean the loop has already started (and Riki remembers this later after discovering the notebook). It’s important to note that at this point, he only admits that he might like her/thinks she is cool, everyone else says they think he’s fallen for her. So he hasn’t realized his feelings himself, so I think it would be a stretch to say he loves her yet, yet it appears the “loop” (or more specifically the memory loss, and therefore the dream world, but maybe not the time loop) is already in effect. The only thing that contradicts slightly is that she requests that he never goes out in the rain again once they confess to each other. My only guess is that the memory loss at this point is much more subtle, and him mentioning it the first time catches her off guard, triggers her memory, and then she fully forgets at a later date.
Quick Timeline (feel free to let me know if I got something wrong):
Sunday, June 17th - Riki asks her on a date to the cafe, she suggest they go the next day
Monday, June 18th - They go on the date, run back to school in the rain, Riki gets sick
Tuesday, June 19th - Riki stays in the dorm, visited by Kurugaya during math, she doesn’t (appear) to remember their date
Time Loop officially begins, days are no longer explicitly mentioned as they were before
First June 20th - Riki gives her a gift from one of the three guys
Second June 20th - Fireworks scene. All other Busters still have their memories at this point.
Third June 20th - First confession scene/rejection
Fourth June 20th - Riki persists, asks her for an answer in broadcast room again, she later approaches him by the vending machine/tea table area and agrees to go out
Fifth June 20th and beyond - Everyone else forgets he and Kurugaya are a couple by this point, dream world is fully realized
This would imply neither of them really fall in love until at least the first June 20th, therefore the time part of the loop shouldn’t have started (although it appears memory loss has already happened). I suppose that implies that she did have feelings beforehand, but maybe didn’t notice/think about it until then (believeable in her case), or what I think is more likely, which is that neither of them really understand the “rules” of the dream world. It also hard to tell because the words “like” and “love” are used somewhat interchangeably (don’t know how else to describe it, maybe something lost in translation from Japanese to English).
The bigger mindfuck for me (which I’m sure I’ll mention whenever I get around to making a full post) is that she writes down that she and Riki are going out and believes it every time (despite her reservations/rejection to going out in the first place, her own view of herself as a person/friend/romantic partner, etc.). The fact that her feelings remain constant throughout might be the most interesting bit for me.