International educational statistics have reported a gender gap in educational outcomes, with boys falling behind girls in regard to grades, high school graduation and university enrollment and retention. This study involved pre-service teachers and school counsellors in Colleges of Education at three universities on three continents carrying out focus groups with public school students, interviews with educators, and examining national and international quantitative data to investigate this issue from a local and a cross cultural perspective. Common themes were found in each country and implications for addressing the problem considered.