Normally, I have like 20 saves for this game each of them are different(4 for solo LI's, Total DIK routes, solo for some "others" girls like riona or nicole) But my main saves are the first ones I play when a new update is out. Sage, Josy and maya, Bella, jill. But a scene in this update made me rethink that decision I may drop jill the next update.
I believe jill unconsciously forces you to become someone else. To explain it better I need to give examples from the other LI's.
When you're alone with Sage in her path, your behavior doesn't change a lot compared to your behavior amongst other friends. You laugh at similar things, you make similar jokes. You're just much more hornier that is all.
In Josy and maya's case, not only you're still the same person you're friends are personally invested in that relationship even if they don't know about it. Derek is hyped as hell to have a brother-in-law. Sage has gotten a lot more closer with Josy and maya. So much closer that separate threesomes or even a foursome is on the table. Tommy may lose his shit at some point but I don't think it will become a huge issue in the end.
On Bella's route, she may complain about your immaturity from time to time but it's obvious that she loves it. It may even makes her feel younger again. You still are your natural self. You don't need to change yourself, your environment to be with her. I'm pretty sure if her being your teacher weren't something frowned upon, most of your friends would adore her. Part of them who got to know Bella already does. Sure just because your friends like her doesn't make her better option in life but I believe it represents how much you need to "adapt" to her.
On jill's route this changes. You're a completely different person when you're with her. You make more PG13 jokes, you're not funny you're goofy. Not only she think less of your friends, she condemns Derek openly. She obviously isn't comfortable with who you're friends are. Don't get me wrong, she's sweet, kind, caring, may be hot if you're into goblins. She really is a good person and I don't think she's manipulative at all but I don't think she's compatible with MC that's all.
I don't know. Maybe I'm making this attitude bigger than it is but that's my 2 cents on the issue.