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This is an interesting topic to me, Kimberly, because I have been on both sides of the canvas. I completely agree that when someone sits for you their beauty becomes apparent. I especially enjoy it when my first impression is of some one who I think is "average looking" becomes very interesting under the lights. I like to find what is unique about a persons features or body and see if I can translate that on the easel. My favorite subjects are children because they are so naturally pretty and most of the time unconscious of what they look like. My least favorite subject is a very made up woman because I feel that what makes them interesting or unique has been covered up.
On the other side, I have modeled for a local artist who made me look absolutely fabulous and while I was flattered I felt they did not really look like me. I took my young daughter to see the paintings at the gallery and her comment was " That fancy lady is not you, Mama!" The artist was standing there, talk about an awkward moment! The painting that I felt looked most like me was done by another artist during a plein air session. She captured me painting at my easel holding pastels in my hand, my hair in a bandanna, wearing jeans and a tee shirt. It was a great painting, definitely not glamorous, but the real me. Our culture stresses such a narrow definition of beauty I think the real fun of portrait painting is to expand that definition and help the subject find out how attractive they really are.
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