That is an awesome idea! Really, that would be very clever for them to do. Jenna's route starts with you choosing her or Leo, it would be pretty interesting if it ends the same way. Like in her route you get to know her more, but I actually kinda find her annoying! Plus Leo seems really aggressive in her route, maybe thats his way of telling Chase that he's hurt to see him hang out with Jenna? It would make sense if the route goes like this; Chase tells Jenna he's bi and gets together with her in the end. Chase tells Jenna he's gay and gets back with Leo in the end, working out their problems. Thats what bothers me about Leos ending, him and Chase never got time to even try to work out their problems and arguments. They have that one conversation, but it didn't help their relationship. Maybe in Jenna route Chase will see how much Leo is actually hurting?