This is an a typical situation so please read the background before replying.
Background: I do private anime art lessons out of my house to kids with a focus on traditional art fundamentals. I've had one college age student for the last 3 years who has Asperger's Syndrome. Its a high functioning form of autism where basically the person is normal but has a difficult time functioning in social situations. Too add to it, he also has a learning disability and a hard time judging spatial relationships. He came to me as not being able to draw and now is at a beginner level and is able to do basic characters from the front, inking and coloring in photoshop. All asperger's sufferers usually have one "Big Thing" in their life that they are completely obsessed with. His happens to be video games.
Problem: While he continues to improve, he's a sophmore who's gotten into a video game design program at a local state university. He got assigned to make a basic 2D game. He's been working his tail off and now has been told by the teacher that his art isn't good enough. He's devastated. As his teacher, friend and confidant, I really care about this boy. I think I can help him push through this assignment but ultimately, he's trying to become something that I think is impossible for him to become. Do I let him down easy now, or do I let him figure it out. I'm not one to discourage people but sometimes the reality of the situation is obvious.
I trust there are a lot of great artists here. Remember, I'm trying not to crush this boy's dreams. I'd love to hear some advice.