This paper reports on data from the first year of a longitudinal study designed to determine the factors associated with adolescents' emotional well-being and academic outcomes. The study commenced in 2003 with over 600 Year 7 students drawn from five Catholic secondary schools in New South Wales. An additional 400 Year 7 students will be added in 2004 and the entire cohort will be tracked to the end of their Year 12 studies. The first year data comprise measures of students' personality factors (self-esteem, conscientiousness, tough-mindedness, attributional styles, and subjective well-being); their perceptions of their parents' parenting styles; their attitudes to school; and their affiliation with peer groups. Additionally, the students' ELLA and SNAP scores and school grades were collected to provide data on their academic achievements. The data reported in this paper were subjected to a one-way MANOVA with gender as the independent factor. Significant gender differences were noted in the students' levels of tough-mindedness, conscientiousness, trait hope, depression, joviality, attitudes to education and positive attributional style. These findings will be outlined in detail and discussed in relation to students' academic achievements. The implications of the findings will also be explored.