There is limited evidence of the effects of culture and context on student readiness for e-learning, and how these might interact with gender. This study addresses this gap by studying the effect of culture and context on the readiness of high school students to use e-learning in a unique setting: an education system in which male and female students are educated separately. A mixed methods research approach was adopted because of our emphasis on the subjective aspect of the concept of readiness. Findings demonstrate that there are clear differences between the genders, but that these must be interpreted carefully in this cultural setting. There is scope for further research that investigates this gender divide in other e-learning contexts, including those where male and female students learn together and those where other cultural factors may influence student readiness to use e-learning.