Friendship contributes to a flourishing life, yet most research and writing on friendship focuses on friends who are demographically similar to one another, known as homophily in social networks. Homophily in friendship is particularly pronounced within and among age and life stage. Yet, friendship between adults with more than 20 years of age difference confers unique benefits to both the older and younger individuals within them. Through a positive psychology lens, this paper reviews the literature on intergenerational friendship and identifies and explores key advantages of intergenerational friendships through a qualitative study of ten individuals in such friendships. Among many benefits, intergenerational friendships offer the younger half of friendship dyads authentic and durable acceptance, deeply meaningful mentorship, enthusiasm for niche hobbies, personal navigation, and a sense of pride in the relationship. This paper also suggests directions for future research of intergenerational friendship, such as the factors that may predispose adults toward intergenerational friendship and methods to amplify the benefits of intergenerational friendship.