This article discusses how the friendship circles of 38 schoolboys in New Zealand influence what they consider acceptable language and behaviour. Six focus group sessions were held with heterosexual and self-identified queer students aged between thirteen and eighteen to explore their interpretations, meanings and usage of homosexually themed language. This article starts by reviewing the intersection of adolescence and schooling as well as the importance of the friendship circle for young men. It then highlights the reported shifting in meaning concerning language, specifically the expression "that's so gay." This study's heterosexual and queer participants argued that for them "that's so gay" has no negative social intent and is just an expression identifying that someone's action, comment or behaviour was not appropriate or right. The findings highlight the contractions and confusions that emerge when an expression with historical negative intentions is used by a younger generation.