Since the beginning of 2000s, reports and research have recognized the thrive of caring masculinities, closely linked to changes in the way men perceive, experience and display their role as affectionate and hands-on fathers. This literature has also highlighted the impact of the reshape of male identities and practices, underpinned by a commitment to caring responsibilities, at different levels: individual, by increasing the wellbeing of children, women and men themselves; familiar, by improving work-life balance and the sharing of responsibilities in the household; and societal, by reducing the social and human costs of the harmful facets of traditional masculinities. This cultural transformation, taking place in many parts of the world, is grounded in social attitudes increasingly favourable to gender equality in the public and the private spheres, specially cherished by young men and women that understand both spheres as fundamental for their self-fulfilment. But it is also being supported by public policies and their legal frameworks under the assumption that “men need gender equality and gender equality needs men” (Scambor et al. 2014), i.e., that men are crucial allies for the development of societies with greater and more inclusive levels of gender equality; and with all-encompassing benefits, including the reduction of the visible costs that women (and the less visible ones that men) have been paying under a gendered, male-dominated world. This paradigmatic shift is being addressed in a new age of parental leave policies, by explicitly encouraging men to share family responsibilities through their involvement in primary and autonomous caregiving. This public recognition of the caring role of fathers – their right as much as their duty to care for their children – is in line with former measures that have been targeting women’s participation in the labour market, including the legal protection of working mothers, so they could overtake the prejudice of maternity and fulfil themselves in the public sphere. Dual-earner/dual-carer couples, full-time working mothers, caring and hands-on fathers are ultimate achievements of this social progress. The legislation on shared parenting after divorce/separation should be understood in the realm of this paradigmatic shift towards public policies committed to gender equality and the sharing of family responsibilities among men and women. However, it is taking place an extensive debate, among several social actors, on its pros and cons, with family violence (implicitly understood as the violence of and adult male over his female partner and/or children) taking the centre stage and bringing the debate into a difficult crossroads. This state of affairs is obviously linked to the social visibility of the costs of harmful facets masculinities. However, sustaining the status quo has several costs as well: maintains the gender bias and gender divide in societies, locking men and women in traditional gender roles and identities; diminishes the potential of the changes that have already taken place in family life, wherein caring masculinities plays a crucial role; hinders the deepening of the pathway towards gender equality in societies, which requires men (as much as women) and their ability to defy hegemonic masculinities. Against the backdrop of Portuguese society, and drawing on results and conclusions of a White Paper on men and gender equality, but also on qualitative research, this presentation intends to contribute for the wider debate proposed by the ICSP-Conference, by bringing an insight on the obstacles that societies still pose to the thrive of caring masculinities, namely in family life.