I'm kinda taking a guess as to what might help you (in case the last response didn't do so), but just in case.. if you're having a hard time finding the girl *two spaces* right of Lily, explore in the outskirts until you meet a goblin. Follow her story line and eventually she reveals herself & becomes a main character.
To increase with Jessica past three, take the train, interact with Gramps in the mountains. He'll get you going in the proper direction.
I tried to avoid as many spoilers as possible, hopefully this is what you needed ;)