I finished this first portrait of Sam (I think is his name) but I am not very happy with it and since his mother is paying me to do this, I want both of us to be happy with it, so I am going to do it again. I think it's the background that bothers me as do the over worked areas around the ears and eyes. My favorite part is the sleeve of his shirt! I just want it to look "fresher" and not so pained. But it is a good study and I learned from doing it. I 'm excited about starting a new one. The reference photo and preliminary sketches can be viewed on the Post from February 20, 2007.
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I don't think it looks pained or overworked, I think it looks great. Give it too her and see what she thinks.
I agree with Desiree, Marta. The eyes and ears are lovely. You've captured character. It's charming and very good.