Witch-tropes such as oversexed maiden, bad mother, or evil crone still dominate depictions of women’s sexuality in mass media. No matter the age of the character, their sexuality is either reigned in through heteronormative, patriarchal structures or depicted as a disruptive social force. Middle-aged or older women’s sexuality remains an especially contested site. At this juncture of witch stereotypes, depictions of motherhood, and older women’s sexuality stands Sex Education’s single, middle-aged mother, sex and relationship therapist, Dr. Jean Milburn. In examining the series’ narrative, aesthetic, and costuming choices, we show how Jean embodies and contests modern conceptions of witch stereotypes. Her narratives are about female empowerment, sex positivity, and the complex expectations and realities of motherhood and ageing. Our analyses of Jean’s depiction show that her character invigorates but also frustrates feminist viewing expectations because she continually fails, as a mother, as a lover, and as a therapist in a hetero-patriarchal world. Her failures are important as they point to the failures of white feminisms and to the work that remains to be done to enact hopeful, feminist, and sex-positive futures.