To be honest, your app is to nice. For example if I got 3 really bad nights with 5hours sleep and the app is telling me "you're on your way" it feels not right. It's like this friend who doesn't tell you the truth, so he's not hurting your feelings. My suggestion is an optional "honest mode" that gives you real feedback even if it's not what the user wants to hear. Or better call it "feedback mode". I know for some people this would be demotivating and the nice mode should be standard, but the option would be nice. In my humble opinion, honest, constructive feedback is what makes people better. Always being nice is not.
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