Dude, you don't even make sense here. The "dates" were only dates to Tybalt. Jill thought of them as an obligation to keep Tybalt from suing or pressing charges (depending on if you punched him or not). There was zero chance at that point that Jill would have any relationship with Tybalt. She literally hated him at that point, but was so non-confrontational, and unwilling to put you at risk, EVEN IF YOU WERE JUST FRIENDS at that point. Jill is extremely nice, and extremely timid.
The point is not that, the point is that She simply Reject you based on an affinity that made by choices that absolutely nothing to do with her ( just like in the Josy Maya case ) ,
and essentially give you a feeling that you are basically tybalt, the guy who blackmailed her. Despite you being nothing but nice toward, her hell might even do a complete solo run help her to make her dream come ture, and yet you are rejected.
Not becasue you fuck stippers or whores, not because you punch tyblat, or even kicking out of his teeth, but simply because in that moment you have a wrong affinity.
Do you know what I do before I visit Jill and her friends in ep 8,
I work at a StripBar, and Fuck Lily , that is tottaly fine becasue I have a Neutral affinity so I'm a good Guy,, someone who is perfectly fine for her
but oh boy if I have Dik affinity and don't do any of that
But I'm gonna be honest with you , there is nothing you can say that change my mind.