The application of school mathematics to real-life situations is emphasised in most countries as a major goal of the mathematics curriculum. Equally, in international comparative tests such as the Trends In Mathematics and Science Study (TIMSS) and Programme for International Student Assessment (PISA) test items dealing with the applications of mathematics to real-life contexts abound. We investigated contexts junior secondary school learners in Swaziland public schools prefer to deal with in mathematics. A survey design was employed with the questionnaire containing both intra- and extra-mathematical items. Non-parametric statistical procedures were used to analyse the responses from the learners. The analysis suggests that learners mostly prefer contexts that they perceive to impact on their future well-being, that involve real-life situations dealing with modern technologies and with those that are of social concern. The open response section of the questionnaire requested learners to provide motivations for their preferred contexts. The use of constructs from identity development and theories about interest suggest that learners' most popular reason for preferring contexts was a perceived value in dealing with real-life situations in their future. Another popular reason was associated with the effects the contexts might have on learning.