For some high school young men, walking through particular parts of the school can be a painful and threatening experience. Whether it is echoed in the distance or murmured under the breath of their peers, “fag,” “freak,” “wuss,” and “gay” are searing reminders of the constant gender work required by young men to prove they are “real men” (see Pascoe, 2007). These terms are intended to signify a failure of masculinity, a failure of living up to a gendered standard of identity. Regardless of whether in fact a man demonstrates a lack of masculinity or an inadequacy in how he presents as masculine, the use of such terms publicly implies and openly denounces particular ways of being men. For high school young men who are ambiguous or outright unwilling to participate in heteronormative practices of masculinity and thus do not “fit” in with the stereotypical interests and actions of their male counterparts, the terms and references above are powerful forms of control over how boys “do boy” in schools. (see Kehler, 2004a; Mills, 2001; Mac An Ghaill, 1996; Martino, 2000, 2001) These tensions become particularly striking in situations when boys “actively shift in and out of different performances of other forms of masculinities available to them depending on their contextual reading of the space, situation at hand and the power relations operating” (Robinson, 2005, p. 23). One such situation is the same-sex friendships developed between boys in a school context (see McLeod, 2002; Renold, 2004; Walker, 1998) Building on Pease (2000), I explore what emerges as an uneasy tension for some high school young men in the development of close same-sex friendships. The focus of this chapter is on describing the close intimate relations of four young men, but I do this in relation to homophobia as a barrier within schools that currently prevents many heterosexual men from establishing male-male friendships.