Here's how i see it.Let's put this into another perspective alright ?
Case Bella: You get fucked because you took her car to take home a fellow teacher ( Cathy
) and you had undeniably sex with her... ( even if it was just a blowjob so the panty in the glove box is not understandable for me... but whatever
) Sooo... you violate several points in judgement that is ( understandably ) important to her...
Case Jill: You blow her off ( THE WAY YOU DO IT !!! ) in her effort to get you a birthday surprise date ??? Really ??? And you tell me you WANT TO BE on her path ?!?
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Because you just need to help Sage when she desperately need you, just that simple action to just ruin your path with Jill even if your not romantically involve with Sage.
May i remind you that the MC is a kind of a good mate, that want to help those in needs as he's doing troughout the game and not helping Sage in time of need, in my advice, would've went again the basic caracter of the MC, which is one of a helping hand when ever he can.