It's interesting when people that certain things aren't "going to end well" because the only reason we're really saying that is because of who the dev is. This game, it's story, and its various relationships could end well, or at least well-ish. There's plenty of scope for some raw emotions, heartbreak, drama, etc, but it needn't be all doom and gloom at the end and could have reasonably OK outcomes, but because it's this dev, people don't suspect that will happen.
Take that Jill/Josy friendship, for example. Each of them know that you've dated the other, yet they seem to be forming a genuine friendship despite the "threat" the other might pose. This could be written to work in a relatively OK way with either them making the MC choose but being somewhat OK if he doesn't choose them because they like the other girl as a friend. However, this being DPC, we're bracing for having out hearts pulled out through our ass by devastatingly upsetting the one that doesn't get chosen, and it's unfortunate that we often have such a cynical view of this game.