The chapter engages with feminist theories of the monstrous, performativity, and new materialism to examine how menstruation is negotiated and performed by young menstruators in the context of YouTube videos. It further asks what menstruation and menstruators can be(come) in the intersection of mediation and multiple cultural, material, affective, and discursive agents at play. By examining two YouTube videos that address menstruation, Andreasen explores how menstruation is entangled with “the monstrous” and how this relation makes new emergences of menstruation and menstruators possible. With the reservation of racial, bodily, and social privileges in mind, the chapter concludes with a proposal for a feminist affirmative critique, where the videos can be read as imaginative work and as possibilities for menstrual change for some.