Before the 2020 publication of Elana K. Arnold’s Red Hood and Sarah Cuthew’s Blood Moon, Judy Blume’s 1970 novel Are You There God? It’s Me, Margaret, which ends with the heroine praising God for blessing her with menarche, was one of the only young adult novels to feature menstruation as a central theme. This paper opens with a brief overview of recent English and American menstrual activism and a discussion of scholarly considerations of the menstrual cycle in literature. Then, through a close comparative reading of works by Arnold and Cuthew, I argue that both novels fulfil their feminist agendas by representing the stigmatised experience of the physicality of menses, and by depicting young women negotiating instances of the kinds of misogyny that punctuate contemporary Western culture. At the same time, the novels share an overly simplistic, binarised attitude towards male adolescents. That aspect highlights the need for the development of affirmative feminist boys studies. Such progress would foster more nuanced literary depictions of young males—and address the challenges of building a more equitable world, thereby responding to some of the motivating concerns of Red Hood and Blood Moon.