Ok so not having played the Jill path, could her mother be the brunette friend in the picture the MC has? On that note maybe the redhead is Sage's birth mother who had to give her up for adoption. Not sure how far back those flashbacks are supposed to be but rich girl gets knocked up by poor guy and rich parents make her give up the child to save face and hide the fact, to marry who they consider worthy. Was a rather big thing at certain points in the past. It was either that or they ran away like Lynnette did being disowned by the family. Would link all 3 character's families in a twist kind of way.