During the adolescence, boys and girls get more involved in the relationships with their friends. Peers are important development context: they offer the possibility to compare with others and the normative reference for experimenting new experiences. The aims of this study are: 1) to describe patterns of stay together with friends as regard to gender, age and different high schools attendance; 2) to investigate the relationships between these patterns and psychosocial well-being (positive self perception and expectations of success) in boys and girls. The sample is constituted of 136 adolescents of both gender, aged from 14 to 20 years, attending different high schools in North-West of Italy. The analyses underlined that: 1) the relevant motivations of friendships are sharing support, and comparison, especially among girls and older adolescents; 2) sharing alone doesn’t ensure an adequate level of well-being, although it is necessary to share with friends positive feelings.