Barbara Pym’s novels of the 1950s are generally devoted to the representation of the life of educated single gentlewomen, but when she does choose to depict men, they do not conform to contemporary ideas of masculinity. This paper demonstrates Pym’s ambiguous treatment of several types of male characters and the traditional association between homosexuality and the Anglo-Catholic faction of the Anglican Church. Although in her presentation Pym refers to popular cultural attitudes and clichés, which were clear to her target audience but have to be explicated today (more than 50 years later), this use of stereotypes does not amount to moral judgment or condemnation. On the contrary, in a decade when homosexuals were outlawed and demonized, Pym represents them sympathetically and their lifestyle as a legitimate and somewhat intriguing choice.