This bit?
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It's about as close as the game gets to acknowledging the reasons M&J will reject the MC. If the MC didn't sleep with Josy in Episode 2, or if he has DIK affinity, Josy will give that line above about not being sure if she has regrets. If, on the other hand, the MC did sleep with her and has Neutral or CHICK affinity, Josy has no regrets:
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In other words, Josy is signalling if she would stand up for the MC if he tries for something more. But this is only from Josy's POV; if the MC is a non-DIK and helped Maya in Episode 3 he could still be accepted. Maya has no equivalent dialog AFAIK. And of course Episode 5 will confuse the matter by having Josy blame the rejection on Maya or the MC even if she does have these regrets. Sigh.
Anyway, the moral of the story is apparently that nice girls never regret sleeping with nice boys. Go figure.