The transition from middle school to high school continues to challenge students, parents, and schools. Parents are recognized as important influences, but the current literature provides limited information about what matters to parents and what role parents may play in determining the success of students making the transition to high school. Gaining better insight from the perspective of parents may assist in providing educators with more useful information for creating and executing more successful transition plans. Parents of current eighth grade students were recruited and agreed to be interviewed twice: first at the beginning of their child's first year of high school and again after the first semester of their child's first year of high school. Parents were asked how they would describe the relationship they share with their child, and what they thought about the transition their child was making from middle school to high school. Although each parent had a unique story to tell, there were connections between each parent story that came to the surface as the interviews were analyzed. Parents reported that the transition to high school was accompanied by their adolescents' growth and development, their increased freedom and independence, and changes in parent-adolescent relationships, all shaped in part by their adolescents' gender. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]