Here is my analysis of the relationship between Jill and the MC so far. It started off with her feeling bad for him on account of the bullying incidents both at the beginning with all the jocks and than the fight with chad. At those instances i don't think she was helping him due to some romantic notions towards him nor due to pity but rather because she is just a caring person in general.
What changed her perception towards the MC in a more romantic way is the catalyst know as Bella. Seeing how Bella was impressed with the MC's character as a person it piqued Jill's interest and depending on our character affinity and the choices we make that interest will keep on growing so to say that she only sees him as this helpless puppy cannot be justified. She sees him as someone special as he doesn't care for her family title nor her wealth but rather her as a person and in her world that's a rarity.
As for the upcoming drama surrounding her i think the whole idea of the MC's mother being related to Jill's family is too far fetched even for a DPC game.Her drama will mainly stem from her family's acceptance of someone from a poor background , tybalt and his watermelons, Bella on account of her being in love with the same man as Jill and Josy and her growing friendship with Jill which will eventually lead to jealousy as both of them have eyes for one dude....that is gonna be
