Recent debates about maternal regret, prompted by the publication of Israeli sociologist Orna Donath’s (2015) research with mothers who admit to regretting their motherhood, have manifested differently in different cultural contexts. This chapter situates Tiina Sihto and Armi Mustosmäki’s analysis of a discussion of regret among contributors to an online forum for mothers in Finland (see Chap. 10.1007/978-981-16-1174-2_10 ) within the international context by comparing the Finnish discussion to similar media debates in Spain and the Anglophone countries. Our analysis reveals that while the idea that a woman might regret her motherhood is more readily accepted in countries where institutional support for mothers is lacking, there is a general acceptance that the inordinate pressures placed on mothers in neoliberal societies to negotiate the competing demands of family and paid employment make it inevitable that some women will experience regret. Moreover, we find evidence that the open conversation about regret triggered by Donath’s research is perceived as a further step towards destabilizing traditional attitudes towards gender roles.