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I understand what you mean, especially with her missing teeth. I photographed a boy a year or two ago who would/could not do a real smile, no matter what. Fifty photos of him produced the same result. In that case, I prefer a genuine relaxed expression, rather than a faked "smiling" one.
Here's what I'd do: when the actual dress comes that will be in the painting I would shoot LOTS more photos, all in the same location and lighting, and I would ask her to just relax and not try to smile. (Explain to the mom ahead of time that you feel that a real, relaxed expression is much better than a pretend smiling one.)
This will give you many more options to choose from, and you can then present half a dozen of the best ones to the Mom to pick, rather than just one or two.
An added and very important benefit of doing this is that you'll have face shots that really match the angle and lighting of the body shots, because you'll have photographed them at the exact same time and place. This will make your life far easier than trying to "match" the lighting from a different day which has great potential for driving you crazy when it comes time to doing the painting. When you're alone in your studio you'll notice all kinds of inconsisentcies between the face and body photos if shot at a different time (camera angle, angle of shoulders, temperature of the light, etc.) Make your job easy: shoot all the face and body shots at exactly the same time and place.
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