Acquiring and performing leisure skills for a teacher does not denote the criterion of ultimate functioning for a teenager. One important criterion for community leisure participation by teenagers includes engaging in those activities with friends. The primary purpose of the present study was to investigate the degree to which leisure skills acquired and demonstrated through instruction would generalize when students were provided opportunities to engage in those same activities with a peer. A secondary purpose was to determine the impact of leisure skill competence by the student with disabilities on social interactions with peers while engaging in leisure activities. A tertiary purpose was to examine the attitudes of the teenagers without disabilities who participated in the study. Results indicated that the increase in skills demonstrated with the instructor were associated with an increase in the demonstration of those same skills when engaged in the activity with a peer. Correlations were calculated between leisure skill demonstration by the student with disabilities and specific social behaviors. Only the skill defined as “cooperative participation” was highly correlated. Attitude scores of the high school peers showed a statistically significant increase following the 4 months of interaction. The implications for intervention approaches to facilitate the acquisition and generalization of leisure skills for students with severe disabilities are discussed.