I agree that this is a big step forward. Has anyone ever told your friend he looks a little like Matt Damon?
Can I be contrary voice and say that something is amiss with the lighting? imo the facial tones lack enough contrast to give the face volume. Has the mid-tone contrast been reduced? Take a look again at the left shot and notice how it has a greater illusion of volume? It pops a little more. Yes it is over exposed, but I would have used the sunlight as your primary source and then the off camera flash to gently fill the shadowed side.
Also... how can both pics be the same exposure? You are adding more light with the flash.