We discuss the recent outcome and wider context of the pivotal Australian legal case Tickle vs. Giggle. Its specifics involve a bloke joining a female-only app, but the case has all encompassing consequences for how single-sex law is interpreted and applied in Australia. With examples from court, such as Sall Grover, Giggle's creator, being fined $10,000 for laughing for 2-seconds and so breaking the tension of faux seriousness in such a ridiculous situation, the case represents so much of the dilemma transgenderism causes for women and institutions. Plus, how the American right came late to care about the trans issue, maternity rights as a break point, why Australia has an advantage over Canada in battling transgenderism, and the backlash to transgenderism as a contributing factor to the rise of populism.