The purpose of this research was to utilise a unique researcher vantage point (as embedded academy coach) to explore the experiences of male youth footballers (14-15 years old) at an English professional football academy. Participant observations and in-depth semi-structured interviews with twelve boys were used to generate data. The analysis focused upon (a) the competitive social organisation of the academy, (b) representations of masculinity (c) emotional proximity and what it means to be ‘friends’ in the academy setting, and (d) attitudes towards homosexuality. My findings highlight the limited ability of boys to develop trust and ‘deep’ friendships in this institutional context. These findings suggest that a hyper-competitive (neoliberal) market-driven rationality penetrates football academies and may play a role in altering the parameters of how ‘friendships’ can be lived and experienced for young people ‘on the inside’ of such institutions. Despite limitations on ‘friendships’ and emotional-proximity inside the academy, there was some evidence of inclusivity (c.f. Anderson, 2009), with regards to attitudes towards homosexuality. However, drawing on the concepts of complicity (Connell, 1987, 1995) and hybridity (c.f. Demetriou, 2001; Bridges, 2014), caution is maintained in describing these youth academy footballers as conclusively inclusive. Implications of these findings, limitations of this study and directions for future research are all discussed.