While we have seen a significant investment in widening participation in Australian higher education, many equity groups remain under-represented. Males from low socio-economic backgrounds are the least likely to pursue higher education and the reasons for their non-participation are complex and arguably under-researched. Integral to the agenda of widening participation is career counselling (in its many forms) that occurs at the secondary school level, and the important role it plays in how young people make decisions about their futures. Unfortunately, in Australian secondary schools today, career counselling remains under-resourced and fragmented, often failing to serve the populations most in need. This article presents research conducted with first-in-family young men from low socioeconomic backgrounds where we document their perspectives on the career counselling they experienced during their secondary education. The data suggests they perceived their experiences as substandard; furthermore, their experiences indicate that career counselling is most effective when delivered by people they trust, highlighting how boys continue to be highly relational learners.