Youth with greater levels of narcissism face a wide array of difficulties in interactions with others. However, there exists a curious lack of research on their close relationships, such as friendships. In this study, we examined associations between narcissism and friendship features over time. Participants were 261 eighth and ninth graders (112 boys; M[subscript age at Time 1] = 14.34, SD = 0.68; 95.4% born in Finland) who completed measures of narcissism at Time 1 (fall of the school year), and friendship nominations as well as three different characteristics of friendship (positive friendship quality, corumination, and conflict) at Time 1 and Time 2 (spring of the school year). When we limited our analyses to participants who were in stable reciprocated friendships, then, for girls, narcissism was negatively associated with Time 2 positive friendship quality as well as corumination. For boys, narcissism was not significantly associated with Time 2 positive friendship quality nor corumination. In addition, higher levels of narcissism predicted greater Time 2 positive friendship quality when the friend scored relatively low on narcissism. Our discussion focuses on the putative mechanisms that might account for differences in the dynamics of friendships of boys and girls with greater narcissistic traits, and why youth with greater narcissism levels might perceive their friendships as having more positive features when their friend is dissimilar.