Hello Jen,
Good luck with the portrait. One of the exciting aspects of our field in my opinion is that with an extra push, we can get beyond almost any trouble in the painting.
I refer to the Old Masters when I have a question about a painting or drawing. It is rare to see teeth in an Old Master portrait. I believe it is a reason why you feel you are getting the 'clown' feeling. My feeling is that the Old Masters, particularly an artist like Rembrandt had an emotional depth in their portraits that is rarely seen today. College graduation photos often have superficial smiles. You may want to play around with the smile if you believe you can do it without losing the likeness.
It is often difficult taking a commission like this for the fact that the person desiring the painting doesn't understand these subtleties (I know I don't know how to spell subtlties) and may choose a weak photo for the artist to work with. But with the right attitude we can gain from any experience. I'd love to see the painting when it is done.
Anthony Emmolo (Happy to be back with the forum after a two year break during a divorce from my wife.)
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