Post-structuralist theories of language and gender have become increasingly attractive to language learning researchers. However, masculinity, as part of a socially and culturally constructed system, in relation to English language learning has rarely been investigated. The current study examines how male English language learners negotiate their masculine subject positions in an English language classroom in Cyprus and how they negotiate masculine intersubjectivities with the researcher apropos of English. Semi-structured interviews, enriched with descriptions of attitudes, feelings, and incidents, were carried out with five male adolescent Greek Cypriot English language learners. Through Frame Analysis, the findings evince how these language learners challenge their usual linguistic and masculine habitus and how they achieve interesubjectivities through the symbolic powers of English, Cypriot Greek, and Standard Greek.