No, Jen is not chronically sad. This is only what, the second time? Her more common expressions are happy, perplexed and disappointed.
This started as a sketch in a crappy sketches pile, but i liked the expression and I wanted to practice using the airbrush using my new (read: old) technique (Looks like I also took the time to refine my inking skills). I guess I finally figured it out. I am very pleased with the tool now.
It LOOKS like she's not wearing anything, but for the sake of evading controversy and to avoid hinting at my laziness, I'll just say she's wearing something. You just can't see it.