This chapter aims to illustrate how the social construction of fatherhood and motherhood are mirrored in the plans of a group of interviewed couples expecting their first child and living in Turin in 2010-2012 (a city in the north-west of Italy). The couples’ perceptions of ‘what’s best for the child’ were used as a lens through which the competing forces of Italian family policy and the dominant gender culture were examined. This at a time when the Italian labour market suffered from the 2007-08 economic crisis. Evaluation of couples’ ideals regarding parenthood and their planned strategies to balance work and family life, necessitated a review of how the transition to motherhood and fatherhood contributed to the ‘doing and undoing’ of gender among the couples. In our analyses, we thus paid particular attention to the role that beliefs, ideals and social representations played in the transition to motherhood and fatherhood among the interviewed couples. Moreover, we analysed the importance couples attributed to their financial resources (income and job-related benefits), social resources (family and social network), social policy and work environments when planning for parental and non-parental childcare arrangements. Our analyses show that traditional ideals about what is the best for the child contributed to constructing distinct roles for the interviewed Italian fathers and mothers-to-be. The couples frequently used these ideals to justify differences in their plans concerning men’s and women’s future career investments, participation in the care of the child and the allocation of domestic work. The accounts of our informants suggested a high level of ambivalence towards the transition to a more traditional division of labour. The more egalitarian couples’ resistance to redefining their own future roles occurred in a context in which public support for shared parenthood is weak and a public debate is lacking.