One thing I have learned about making portraits of people is that nearly everyone has a "portrait face" that they put on when I first start shooting. Most often it is a genuinely accommodating (and well-meaning) forced smile. It usually takes an hour or two for us to get comfortable enough with one another for the model to relax and show his or her personality to me and my camera.
Lorena is one of my favorite models to work with. One reason is that her initial portrait face, while still very much a portrait face, produces really good portraits, even before she gets comfortable. You've seen it—a beautiful, placid demi-grin and a cool but friendly look in her eye. This little portrait shoot we did was the first time I've worked with her for long enough to reveal a less edited side of her personality.
This is what I love about this particular photo. Compared to every photo I've taken (and most that I've seen) of Lorena, her expression here takes me completely by surprise. There's a searching, a questioning, and an unstudied ease to her pose and expression that I've never before captured. And the bones and structure of her face are revealed in a different light as a result.
Strobist stuff: Lumopro 160, at probably around 1/8 power, firing through a diffusion umbrella at camera left, about three feet above subject. Cloudy afternoon sun coming through big windows at camera right.