I was quite skeptical at first because this whole conversation is hard to follow; just plenty "basically confirmed" over and over without much proof or content, slapping adverbs as if it'd bring creditability; and I can't tell whether Selly was confirming Molly losing V-card that night, or the meaning of checkmarks, or both (not to mention the lack of clarification on the definition of rape). But assuming both to be confirmed can actually solve the checkmark thing pretty seamlessly.
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If you fuck Ami, numbers of checkmarks are 4 and 7 at 2nd and 4th reset, respectively. So it'd be:
At 2nd reset: Maya, Ami, Ayane, Makoto
At 4th reset: Maya, Ami, Ayane, Makoto, Chika, Kirin, Molly
At some point plenty of us here were trying to figure out what those checkmarks were; someone pointed out that Maya could be a possibility but the math still wouldn't work when it came to the 4th reset because I think no one factored Molly in (also FYI, there are only two versions of source images of these checkmarks; which version is used is only amifingered-dependent, meaning these checkmarks have nothing to do with your decisions with MILFs). But now putting Molly into the equation makes it work again.
I guess the short synopsis is that (1) Molly really got dicked, and (2) a checkmark means a V-card. And if Maya does count, that means it doesn't have to happen within the loops. The owner of the V-card may or may not need to be a minor.