For many bright students, school is a painful experience. Consequently, many parents simply decide to shop around for the high schools which will be the "best fit" to enable their students to experience happiness, to thrive, and to achieve their postgraduate dreams. For many other families in today's society, the need for new jobs and relocation initiates the search for the best high schools in new communities. To complicate this decision, colleges are receiving record numbers of qualified applications each year, so college entrance requirements continue to be ramped up. Therefore, the success of a student's high school experience has become essential to keep postgraduate doors open. This article discusses the factors to consider when determining the "best fit" for a particular student.