D'aww, I love you too.
Is the game impossible? No one has gotten the medal (except someone who got it days before the game was released), so it appears that way. If it is, then why have the medal in the first place? If it's not, then obviously something is wrong with the game mechanics.
I was able to paint the final masterpiece, but then after that it seems pointless to continue. You only repaint same things over again, and no matter what combo I tried, everything just hits a stalemate once you have the happiness level drop while he's sleeping. I was very disappointed when after the masterpiece was made, that there was no game change. Seemed like a milestone for the character, to have no effect.
I get that you're trying to portray a message, but I feel the message is overruled by the frustration level. At least it was for me. This guy is a doomed soul, I don't want to get depressed by playing your game LOL.
However, I really did like the idea of depression setting in once the happiness level got too low, which resulted in quicker happiness depletion. Same with alcoholism, with the tiredness level. And the progressing "thoughts" were entertaining as well.
Long in short, neat game with a message, but way too frustrating to win, if it's even possible. Also, how do you get the "Screw Art!" medal? I've tried a few things, but cannot figure it out!