The word Casanova is often treated as a synonym for womaniser, variously interpreted in a positive or negative light depending upon the audience. The Seduction Community (SC) largely comprises young heterosexual men who follow and adapt the teachings of commercial pick-up artists, typically in an effort to embody the Casanova-myth. This paper reports and analyses findings from a qualitative study of the SC. Drawing from life history interviews (n=29) and understandings generated during fieldwork in California in 2009 and 2013, the paper explores the meanings of the Casanova-myth qua urban legend. As explained in studies that view modern society as a 'folk community', urban legends help mediate anxieties following the Great Transformation in American community life. However, this paper contends that such legends may also produce the same gender anxieties they aim to ameliorate. Lascivious myth-making, which finds clear expression within the rationalised SC, constitutes a double-edged sword under conditions of rapid social change comprising confluent intimacies and the potential marketisation of everything.