You know speaking of Bella and her relationship with Jill. I had started to wonder if what Bella said to the MC was purely to get him on a date with herself, a scare tactic, or if she actually believes what she said? Perhaps a combination of all three?

Just want to see other peoples thoughts on this. Bella tells the MC that to get along with/closer to Jill he HAS to get along with her (making it seem that her word in some ways would even be absolute to an extent), yet things I've seen in this game kind of contradict that. While I'm sure Jill looks to Bella for advice and respects her opinion; I'm just not as convinced it's was to the degree Bella made it out to be.
For one Bella hates Tybalt and has verbally told this to Jill on many occasions I'm sure. Pretty sure she's even explained in detail as to why this is the case to Jill at some point off screen as well. But none of this has stopped Jill from trusting Tybalt, befriending him, or hanging around him.

In the same respect (forgive me if Im wrong here) but I think I remember that if you don't get Bella's approval but still have enough points with Jill you can ask her out regardless and she'll accept the date. I could be wrong its hard to remember everything when you've done multiple playthroughs on various routes. lol That's not saying Jill is supposed to be a robot. Of course she's going to make her own decision like any normal young adult would, regardless of what Bella says if Jill's interested enough in an individual.