Great portrait. I like the shallow depth of field and the darker background. Red was a nice choice. I do find the glare on the upper lip somewhat distracting. Perhaps you could have done some cloning or something to remove that. You did a very nice job controlling the light on the glasses.
The shot isn't doing it for me. Not sure if it is the tight crop, the angle of the head, the lighting... but something is throwing it off to me. I think that if you would have softened the skin a little, added a warm glow to the skin, it may have made an interesting difference.
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