This paper is a preliminary report on using text complexity measurement in the service of a new educational application. We describe a reading intervention where a child takes turns reading a book aloud with a virtual reading partner. Our ultimate goal is to provide meaningful feedback to the parent or the teacher by continuously tracking the child’s improvement in reading fluency. We show that this would not be a simple endeavor, due to an intricate relationship between text complexity from the point of view of comprehension and reading rate.