The ability of fish to recognize and preferentially associate with familiar conspecifics has been well documented in a series of laboratory experiments. In this paper we investigate the schooling preferences of wild female guppies, Poecilia reticulata, in the Upper Tunapuna River in Trinidad and confirm that they do indeed prefer to associate with familiar individuals. The guppies in this river occur in a series of pools that become isolated during the dry season. These fish interact solely with other individuals in their pool for periods of several months at a time and thus have ample opportunity to become accustomed to one another. Our study also reveals that the tendency of female guppies to school with familiar fish declines as the group size in which they naturally live increases. Preferences are strong when there are small numbers of females in a pool, but diminish thereafter. This indicates that the expression of familiarity is constrained by group size. The basis of recognition and the consequences of schooling preferences for familiar individuals are discussed.