The role that physical attractiveness and fluctuating asymmetry (FA), a measure of developmental instability, play in self-perception and peer associations were explored in a well-studied cohort of Jamaican children using a novel research paradigm where subjects were already known to each other for extensive periods of time. The results showed that how attractive a child was perceived by others was significantly positively correlated with self-ratings of attractiveness. Contrary to findings from WEIRD (Western, Educated, Industrialized, Rich, Democratic) samples, the study found a reversal in the sex differences in self-perceived attractiveness and self-esteem, where Jamaican females rate themselves more attractive and report higher self-esteem than do males. Attractiveness also predicts overall popularity, as measured by desirability as a friend and the percentage of peers who choose an individual as a friend. Attractive individuals of both sexes were chosen more often as ‘friends’. A significant correlation was also found between an individual’s FA and the average FA of those chosen as friends. However, the effect was primarily due to preferences by males for female friends possessing similar levels of FA, which could be an effective strategy in reducing future mating effort.