In robotics there’s is this phenomenon called “the uncanny valley”. It describes how humans have no problem getting emotionally attached to something that clearly isn’t trying to look humanoid; but once you start to make something that actually resembles a human the subtle differences act as a repulsive force to actual humans. It’s so much easier to get humans to love their square phones (that talk to them) than it is a plastic human-shaped robot that also talks but has dead-eyes for example.
I think there’s a bit of that uncanny valley phenomenon in representational art as well. I’ve noticed that people can feel a deep emotional attachment to a few sketchy brushstrokes that merely suggest a person, but as you attempt an actual mimetic likeness it really becomes all about the idiosyncrasies that don’t quite line up with objective reality.
I’ve struggled with this particular painting quite a bit more than I had expected to. There’s still a long way to go with it and there are issues yet to be resolved, but I do feel like I’m finally starting to bridge the gap of the uncanny valley with this one. A couple more sessions on the face and clothing and hopefully it will be there. I just hope I haven’t overworked it at that point.