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This is quite a nice drawing, Jonathan, and it's not difficult to visualize the very lovely oil portrait for which the drawing would serve as a study. (You say it's an older drawing, but perhaps the model is still available for for an extended pose --?)
I would make only two observations, one about lighting and its effect on shape and value, and the other on a point of drawing.
I think you would like the form-creating effect of making your shadow shapes (and some of the darker halftones) on the face a little darker and the edges of those shapes better defined. It appears that you've got a pretty strong light source from the left side, which will create shadows darker and more definite than the ones you've drawn. Transitioning (blending) between those shadows and the halftones and light areas around them is something to deal with much later than the establishing of the major shapes and their values. Imagine that you had only, say, 5 sheets of construction paper, in values ranging from very light to very gray, and you had to represent the major value shapes on your model using only those five tones. As you "construct" the figure, constantly check RELATIVE values; ask yourself, is this next area lighter than or darker than the area next to it? If your shapes and values are correct, the subject of your portrait should be identifiable even at that early stage. (And if not, all the fussing and fiddling in the world probably won't help you get a likeness later on.)
When it does come time to join those shapes together, don't just shade a stripe of midtone between them, or drag a tortillion all the way around the shapes' borders. Some edges do need to be softened, yes, but some need to be left quite hard (as where the plane of the form turns sharply away from the light). I wish I had a good pencil drawing on the computer, but I don't, so to keep with the black and white simplicity, I'll try to attach a grisaille oil study of a plaster cast. (I hope it makes the trip with this note; I don't get along very well with my own computer, much less with Internet and cross-platform issues.) Note how dark are some of the shadows on the face (not just the neck), and how sharp the edges of those shadow shapes in some areas, and how much softer in other areas. That's what creates the illusion of form. (Don't forget this effect on the blouse, too, which will be much lighter/darker on one side than the other.)
The other thing I wanted to mention related to drawing of the features. At first, I thought the eye on the right side was slightly too high, but the more I looked at it, the more I felt something else was going on. In fact, if you view the features -- eyes, nose, mouth only, not any of the rest of the face -- through the "viewfinder" of your curled fingers, they're perfect in relation to each other. But as a group, they have a slight tilt to the left that the head doesn't have right now. Give the head that same slight turn and tilt by moving the center of the chin to the right, so that it's underneath the center of the lips (right now, it's underneath the nostril on the left.) This will also have the beneficial effect of moving the centerline of the chin off the line of the shadow on the neck.
Keep at it, you're well along.
Steven
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