Nice looking game, great work. Although the majority of the enemies look better than the main hero. I think you can add some character to the um, main character with additional detail.
:D
Nice artwork. I knew it wasn't possible to consider this idea the moment I saw it, but I wanted to find enough time to write a thorough response.
First, there are the technical limitations. Some of those designs are impossible to implement with ascii, unless you are doing
ascii-like art. The best way I can see to achieve that idea would be to forgo text and use regular sprites. I can understand it from a conceptual point of view. With some changes that idea could be made to work in actual ascii, if not for the fact Stone Story is implemented in monospace font. The amount of suggested detail simply cannot fit into the game's resolution. That is to say, the monospace constraint is not merely a style choice, but a guiding principle of the project that will not bend.
Furthermore, the main character is consciously elementary. An exercise in reduction to the fundamental form of a human's body. Enter the magic of the human brain. We universally see a circle and a few lines and conclude that it's a person. I don't know about you, but that blows my mind. The lack of expression unlocks an additional mechanic, it allows your brain to fill in the blank with whatever expression or likeness it wants. It's not easy to think about how the mind thinks, but we can try. This move from specific/detailed to abstract/symbolic has been studied before, and I wanted to explore one possible limit with Stone Story. I admit some of the enemies have gained too much detail, but I hope the limitations of monospaced and mono-colored ascii assures it can't deviate too much from this goal.
From the single circle for a head sprawled several design aspects, including but not limited to symbolism. Let's go there some other day.
Suffice to say, if facial expressions otherwise made sense, from a production point of view it would be irresponsible, as much of game would have to be redone. One sure way to never finish a game is to keep changing the design.
That said, I really do appreciate ideas and rest assured there will be "hats" in one form or another. There is one important item which modifies your head symbol. This is designed but not yet implemented. For a current implementation take a look at this guy. It's up to you what you think his head features actually are.