This article reports the results of a study which aimed to examine the development of children’s ability to depict loneliness in their drawings. Seventy-eight children and 20 adults took part in the study. Participants were first asked a series of questions assessing their conceptions of loneliness, and were then invited to draw a picture that conveys loneliness. The resulting drawings were coded and scored for the presence of the two dimensions of loneliness: cognitive and emotional. First, the authors examined the use by participants of graphic indicators denoting deficiencies in one’s social relations resulting to loneliness (cognitive dimension); second, they assessed the expressive strategies participants employed to convey the negative affect that typically accompanies loneliness in their drawings (emotional dimension). Finally, the authors tested the relationship between children’s definitions of loneliness with their drawings of the construct. The results show a clear developmental progression in children’s pictorial representations of loneliness. Whereas the majority of young children represented loneliness as the absence of a social network, older children used graphic indicators to convey both the absence of a social network and the sadness that accompanies loneliness. In contrast to children, adults consistently included symbolic or metaphoric graphic indicators in their drawings to convey the negative affect accompanying the experience of loneliness.