Throughout his life, Vaughan Williams was a notorious flirt. This love of women and flirtation permeates not only his music, but his professional and personal relationships alike. Yet, perhaps somewhat paradoxically, Vaughan Williams was also a strong advocate for many women who sought to develop professional careers in the male-dominated music world. This conflict between his behaviour and actions presents a conundrum for those looking to investigate his broader advocacy of women on the one hand and his private behaviour on the other. This chapter explores the contradictory nature of Vaughan Williams’s behaviour and beliefs, from his period of teaching at the Royal College of Music, to the emergence of the nickname ‘Uncle Ralph’ and all that name entailed, revealing a more complex portrait than has hitherto been proposed of the composer’s relationship with his female composition students, in particular.