Young, more numerous, socially active, with a newly positive image, increasingly involved in games of family solidarity, and having a close relationship with their grandchildren in a framework of new bonds of affection: these are some of the features of the new portrait of grandparenthood. In reality, the range is quite wide since the art of being grandparents, and the way in which grandparents play their role, for different reasons, can vary. This article invites us to ask ourselves about the social, cultural and psychological conditions that favour and hinder both the construction of the grandparents’ identity, and how they perform their functions in a transforming society. In this work, grandparenthood is considered as: a) a challenge between generations, with regard to which we investigate the principle of keeping a “good distance” as the normative rule; b) a stage in life that implies a new definition of gender identities and attributions of roles within the couple, with regard to which we specifically dwell on the figure of the grandfather.