Although apartheid officially ended in 1994, race as a primary marker of identity hascontinued to permeate many aspects of private and public life post-apartheid. For young people growing up in the ‘new’ South Africa, the terrain of racial positioning is difficult and uneven. Referred to as the ‘born frees’, they aspire to be liberated of the past yet are themselves shaped by and positioned within its legacy. While a number of scholars have explored the racial positioning of students in historically white institutions (or partly white in the case of the merged institutions), little research has been conducted on racialised discourses in institutions which can be described as historically black. This paper seeks to address this gap by reporting on the racial positioning in the discourses of students at the University of the Western Cape (UWC), South Africa. The data consist of six focus group interviews held on campus between 2009 and 2014. Working with Nuttall’s (2009) notion of ‘entanglement’, and using a focus on narrative, in particular ‘small stories’ (cf. Bamberg &Georgakopoulou 2008), this paper explores how their stories provide insight into the complex and dialogic ways in which they discursively negotiate the racialised identities and discourses of both the past and the present and seek to imagine the future.