The world of fine arts can seem a bit intimidating to a student, and it is part of the teacher's role to help ease students into that world. One of this author's goals as an art and design educator is to bring the world of his students into classroom projects, providing a sense of comfort and familiarity in the context of learning something new. In this article, the author describes how he connected the traditional subject matter of portraiture with the current trends of students, inhabiting the digital realm in the form of digital avatars. (Contains 2 online resources.)