The television series Crazy Ex-Girlfriend and PEN15 are contemporary cringe comedies that foreground female experience. While the vast majority of cringe comedies employ documentary form and/or practice and speak insistently in the present tense, Crazy Ex-Girlfriend and PEN15 produce stories that not only unfold in the present, but also reframe the past, thereby building into their acts of narration, and by extension their cringe esthetics, a retrospective temporality. In light of themes taken up by both series—themes related to mental health and the construction of female identity and desire—this reframing has significant effects both politically and therapeutically. In this article I analyze the formal means by which a retrospective temporality of cringe is achieved in these series, including the use of musical numbers in Crazy Ex-Girlfriend and unconventional casting in PEN15, and I explore the various prosocial effects that temporality produces for the series’ characters, creators, and spectators.