The creation and cultivation of an imaginary companion is considered to be a healthy form of pretend play in early childhood, but there tends to be a less positive view of older children who have them. To test the extent that having an imaginary companion in middle school is associated with positive or negative outcomes, an ethnically diverse sample of 152 middle school children at high risk for developing problem behaviors were interviewed about imaginary companions, coping styles, and problem behaviors. Although having a current imaginary companion (n = 13) was associated with using more positive coping strategies, peer nomination data indicated that these children had low social preference with peers. In addition, our data indicated that these children were perceived by their parents as having more problem behaviors compared with young adolescents who never had imaginary companions (n = 108) or children who had imaginary companions in the past (n = 31). However, a longitudinal follow-up at the end of high school indicated that the children who had imaginary companions in middle school showed greater positive adjustment on a multiple-indicator adjustment construct. (Contains 1 table.)