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Ive done it
Took me almost 3 months but i've reached up to date with every character
Tho Darius one is weird, its the only route where Richard confess his feeling for Maria.And its the route that kinda tangled with Spencers route since both are related to them dating.

Yeah, noticed that as well. There are hints in the other routes that Richard likes her quite a bit. Odd that it only happens in Darius' route. Felt really bad for Spencer during his route though, since I did his one before Darius'. Giving me all the know-how of what Spencer really feels. Makes me wonder if there is a "kind of" canon route in this game.

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It has been confirmed by Dyne that Spencer's route is a canon one.

I think the reason Richard was more pro-active with Maria in Darius's route is because Darius came by the shelter in both his classic car (which Maria immediately knew the year and model of) and his custom motercycle (which Maria also loved) with the Main Character (MC). None of the other routes characters had anything special vehicle wise like that. 

Darius also did other things to spoil her and I think Richard ended up feeling a bit threatened/jealous of how Maria was reacting to Darius. Hence Richard making that purchase (to surpirse Maria) and his opening up to her about how he feels. 

Of couse, Richard was none too shy about his interest in Darius too, if the MC didn't go after him. I look forward to Richard's route coming out. I think it's really going to be something different.