Western Tibetan Buddhist movements have been described as bourgeois and puritanical in previous scholarship. In contrast, Ole Nydahl’s convert lay Karma Kagyu Buddhist movement, the Diamond Way, has drawn attention for its apparently hedonistic style. Focussing on the interpretation of Nydahl’s approach to gender and sexualities, this paper addresses the wider issues of continuity and change during the transition of Tibetan Buddhism from Asia to the West. Nydahl’s pre-modern gender stereotyping, the hetero-machismo of the Diamond Way and the mildly homophobic tone and content of Nydahl’s teaching are interpreted on the background of Indian and Tibetan Buddhist sexual ethics and traditional Tibetan cultural attitudes on sexualities. By excavating the emic genealogy of Nydahl’s teachings, the paper suggests that Nydahl’s and the Diamond Way’s view on and performance of gender and sexualities are consistent with his propagation of convert Buddhist neo-orthodoxy.