This article explores the way young people's responses to an image evolve when they engage with it repeatedly. An analysis of the sequential encounters of six adolescents with a Renaissance painting reveals that, as they gained experience with the picture, the youngsters probed for increasingly deeper layers of meaning in the work. Specifically, on their second encounter with the painting, the students showed greater sensitivity to visual information, and they incorporated their own experiences and knowledge into the meaning-making process more actively than on their first encounter. This study also shows that, once the participants had established a relationship with the artwork on their own terms, they seemed eager to discover contextual information about it. However, far from accepting this information as "authority," the young viewers considered it critically and used it to deepen, expand and revise their personal visions of the painting.