Students with internalizing behaviors are often overlooked in terms of receiving interventions that could change academic outcomes and prevent problems that could have serious implications, including social withdrawal, social isolation, and suicidal ideation. Recent research has found the use of social emotional learning (SEL), school-wide positive behavior support (SWPBS), and social skill instruction, to be effective in treating students with both internalizing and externalizing behavior problems. The use of peers has also shown promise in helping students with behavior problems. In this study, a multiple baseline across participants' design was used across two playgrounds to evaluate a buddy bench intervention, which utilized peers to help socially withdrawn students increase social engagement and peer interactions and decrease social isolation. All students (N = 448) in grades 1st through 6th were observed during the pre-lunch recess period. Results revealed that from baseline to intervention phases there was a decrease of between 19% (on the 4th to 6th grade playground) and 24% (on the 1st to 3rd grade playground) in the number of students engaged in solitary behavior on the playground. The majority of students reported positive attitudes towards the intervention. Teachers reported mixed feelings about the social validity of the Buddy Bench. Limitations and implications are discussed.