The present study revisits the link between culture, gender, language level, and learner's choice of language learning strategies. This is done by answering three questions: (1) what are the major Strategy Inventory of Language Learning (SILL) factors in Kuwait (a hybrid context)? (2) Which factors are related to gender? And (3) which factors are related to language level? The results of the study indicate a relationship between gender and active naturalistic language use, cognitive-compensatory strategies and repetition-revision strategies. They also indicate a relationship between language level and active naturalistic strategies and affective strategies. Based on these results, it is proposed that learning contexts in a cultural milieu are perhaps the strongest variable affecting strategy choice. Finally, proposals are made for a more contextualized approach to strategy research.