I have it lucky because most of the senior portrait sessions I do are with students I know well. I am a middle school and high school teacher and so the relationships I make with students over many years really help me know what to bring out and capture. I have known CJ, pictured below, since he was in 6th grade and now he is going off to college. When I have built trust with a student over years, it is much easier to get into the moment together, have fun and sort of play act. Movement and a sense of adventure are key to getting young people out of themselves. For CJ's photo shoot, we met at the PS Art Museum for interesting angles in the architecture, then we drove around neighborhoods in old Las Palmas Palm Springs to look for interesting doors and flora. We had planned to go to the windmills (I always ask where someone would like to shoot so their personality is more in the photo). On our way to the windmills, there was a train stopped in the desert. I intuitively knew to stop and shoot there because I know CJ. It just so happens that trains were his very favorite thing when he was little. It was an adventurous time as we got on the train when we probably shouldn't have and another train blew by.
What do I do when I don't know someone well whom I am taking portraits of? I get the person to move so they can get in the present moment. The more playful I can get the subject, even when the shoot is serious, the better pictures I get.