To me, this looks a little too dark on her left side (camera right). Perhaps a reflector would add some fill to bring that side of her face out of the shadows. Other than that, a great attempt a meeting the challenge head-on.
Wow! Talk about up close and personal. I like it. Just a tad too light. I wouldn't have minded if it were darkened a bit. But then agin that is my own persoonal taste. BOL
Gentle sympathetic portrait. I like the soft focus, although I note some of her hair is in focus, which takes one's eye away from the subject. The lighting is well controlled, low contrast but still providing detail in the shadows
Seems like this has a very shallow DOF and that the focus is based off the rim of the glasses over the subject's left eye. This leaves the eyes slightly mushy and not crisply distinct. You could use the polygon tool in PS to select around the left eye as that side of the face is lit and then perform a selective curves to brighten up that eye a litlte.
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