This article sets out to analyze how older women understand grandmotherhood. In-depth interviews were conducted with 25 elderly women from Quebec with diverse lives (widowed, married, single, with or without children) drawn from three generations (65–74 years, 75–84 years, 85 years and over) according to principles of qualitative analysis using grounded theory. Based on a constructivist approach, results highlight the evolution of images of grandmotherhood offering the benefit of emotional, playful and comforting roles. This analysis also reveals multiple ways of being a grandmother and commitments that vary according to three principal factors: (1) the personality and life trajectory of the grandmothers; (2) the family situation and role of crisis in the family; and (3) the degree of intimacy with grandchildren. There follows a discussion on the place and role of the family in the lives of older women today.