I have been getting lucky with Senior Portraits--one is leading to another, and another... This is a friend of my nephew's and he isn't one for pictures, or smiling. Pretty much if his mom didn't want these, I don't think we would have done them.
Rather then pose him in a Polo shirt and make him smile in front of a muslin, we all agreed we need to shoot him with what he likes--jeans, a t-shirt and his Jeep.
We drove not far from his house to this spot in the desert and I setup my dual speedlight softbox on a tripod--it works great on uneven ground like this. I use 2 580EXs and fire one with an extended ETTL cord, the other mimics its settings thanks to Canon Wireless, so all I have to set is one flash.
I am loving this setup as all I really do is get the light on my subject the way I like it, and then balance that with the ambient.
I am also loving the new 5D II. I don't have to do near the post work I used to. I am getting more shots ready to go out of camera then ever!
After all was said and done, it didn't seem like he hated it too much!