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In this paper, I examine how work-family arrangements during the transition to parenthood are made in a context of a recent and fast-paced increase in gender equity in the labor force combined with traditional gendered norms around parenthood and strong work devotion expectations. Many second-wave developing countries experience incoherence between institutional gender equity and family gender equity—as women become increasingly educated and employed in a household context of traditional gender norms they might experience higher levels of work-family conflict. Work-family policies further shape this process, as they determine what is available as an option. However, we do now know much about how individuals are making decisions in a context of incoherence and widespread availability of paid parental leave. To fill this gap, I use interview data from Chile, from different-sex professional couples who are expecting this first child as well as individuals who work in supervisory positions in the same professions. The findings suggest that the plans and expectations around parenthood and work are very gendered, which I argue in part is associated with the parental leave policy in Chile. Women work to reduce the backlash of maternity leave—both by “deserving” the leave and avoiding confirming the stereotype of "taking advantage." Further, paternity leave is not seen as an option by expecting fathers and is legitimated by employers—suggesting that traditional gender norms around parenthood and division of work are pervasive and restricting the chances than men use paternity leave benefits.