Catching the personality with a smile is very difficult. More practice is needed catching someone’s smile. My oldest daughter and son-in-law make a beautiful couple.
I screwed up on Jason’s teeth. One of the reasons I am drawing portraits, I am horrible at hands and teeth, a smile scares the heck out of me. No more avoiding my fears or mistakes. To make matters worse, I tried to fix my mistake with gouache paint. Learned my lesson, start light and use the darkness modestly and avoid mixing mediums unless you plan to form the get-go.