Leisure activities play an important role in the lives of families, among couples, in parent-child relations, and in grandparent-grandchild relations (Lawton, Silverstein, & Bengtson, 1994; Menec & Chipperfield, 1997; Norris et al., 2004; Szinovacz & Davey, 2001, 2004). Researchers have found that leisure has a positive influence on family relationships by enhancing communication and cohesion among family members (Orthner & Mancini, 1990). Other studies have shown that family leisure may not be mutually satisfying for all family members and may cause substantial stress among mothers in particular (Shaw & Dawson, 2003). Research focusing specifically on family leisure, however, has excluded the voices of older adults and has, instead, focused mainly on heterosexual married couples with young children. The purpose of this interpretive study, therefore, was to develop an in-depth understanding of the experience of intergenerational family leisure for grandparents and their adult grandchildren. Fourteen dyads of grandparents and adult grandchildren were interviewed individually and were asked to describe their experience of intergenerational family leisure. Using grounded theory methods to analyze the interview data, the stories of the grandparents and grandchildren provided valuable insight into the role that leisure plays in the intergenerational relationship. The theorizing undertaken in the current study advances our understanding of grandparent-grandchild relationships and suggests conceptual connections between three important theoretical concepts: intergenerational ambivalence, intergenerational stake, and generativity. Family leisure is a critical context for the development and expression of these three concepts. Generativity appears to develop across the life course and plays a central role in the family leisure experiences for both grandparents and their adult grandchildren. Generativity also appears to influence the experience of intergenerational stake and suggests that grandparents who have stronger generative commitments may experience greater stake in their relationship than their grandchildren. This perception of intergenerational stake, in turn, is linked to the experience of intergenerational ambivalence. When grandchildren perceive that their grandparents have a stronger investment in their relationship than they do, they experience greater ambivalence. This ambivalence results from the grandchildren's inability to reconcile the normative, structural expectations related to the need to spend time with their grandparents with their need to participate in a variety of other social relationships e.g., peers, romantic partners. Family leisure, therefore, is a crucial lens for the study of intergenerational relations and the interconnections among these three concepts.