In 2018, Taylor Swift asserted her political advocacy to a public extent she had not previously done. Controversially, Swift’s music video ‘You Need to Calm Down’ (2019) showcased LGBTQ celebrities and aligned her with Katy Perry, whose similar identification as an LGBTQ ally has met stark criticism. As with Perry, I argue, criticism towards Swift’s advocacy involves unspoken tensions with gender, genre, and commerce. To untangle these tensions, I examine several assumptions: that Swift’s advocacy is exploitive and performative, that she conflates LGBTQ discrimination with her own struggles, and that she may have misled the public by feigning bisexuality. Using statements by critics, Instagram and Twitter posts, and footage from Swift’s documentary Miss Americana (2020), I argue that insightful criticisms towards Swift’s allyship are mixed with uncharitable and reductive mischaracterizations of her work. Comparing two approaches to interpreting her video, I argue that objections to Swift’s conflating personal problems with systemic discrimination make unnecessary assumptions about how narratives work in her song and video. I further examine how suspicions around queerbaiting draw on rumours and the circular citations of conspiratorial hermeneutics. Critics have long villainized Swift for her dating life and its role in her lyrics, revealing a distrust of young female subjectivity difficult to separate from the distrust of Swift’s political competence and intensions. By separating concerns with rainbow capitalism from spurious claims about intent and misogynistic fusions of mass culture with womanhood, I hope to achieve a more tempered assessment of Swift’s politics.