Listening is an important skill for all, but it is critical for musicians and those who love music. National Standard 6 calls for students to listen to, analyze, and describe a wide variety of music. This listening, analysis, and description can pose challenges for older students who are familiar with a narrow repertoire and accustomed to music as background to other activities. In addition, many middle and high school students have already developed strong musical preferences that are an integral part of their sense of identity. Planning activities that create meaningful connections between students and diverse listening selections can be an overwhelming proposition. However, with careful planning, listening can become an exciting component of secondary music programs. This article discusses the steps in planning a meaningful listening experience for middle and high school students. Listening experiences are important in creating well-rounded musicians. When teachers choose material carefully, prepare their students fully, and present activities that encourage active listening, they build meaningful connections between their students and music. By challenging themselves and their students to listen to, analyze, and describe a diverse selection of music, they open up a whole new world of musical possibilities.