The purpose of the current study was to examine parent-adolescent interactions within the context of the transition to high school. Ten parent-adolescent dyads from a medium sized and large sized community participated in the present study. Each parent-adolescent dyad engaged in a self-generated, self-directed conversation about the transition to high school and were videotaped. Immediately after the conversation, each parent and adolescent separately viewed a playback of the conversation, and were asked to report their thoughts and feelings. Thematic analysis and Baxter's (1988, 2004) relational dialectics theory were used to analyze the conversations and the video recall sessions (Braun & Clarke, 2006). Results uncovered specific themes and dialectics from the conversations and video recall sessions.