The significance of producing socially appropriate utterances, not just linguistically correct ones, has given rise to a plethora of studies on speech acts. In this regard, the performance of second and foreign language learners against the norms of the target language and the factors affecting them have yet to be thoroughly investigated. To contribute to this ongoing research, this study aimed to elicit pragmatic requestive features of Iranian EFL (English as a Foreign Language) learners with respect to (a) request directness, (b) request perspective, (c) internal modification, and (d) external modification in eight social situations. This study also examined whether language proficiency and two contextual factors of social power and social distance affect Iranian EFL learners' requests in English. Participants were a total of 60 university students or graduates who had taken TOEFL in the past 2 years and were thus categorized into low and high proficiency levels. A Written Discourse Completion Test (WDCT) was employed to elicit requests. To achieve the objectives of this study, both descriptive statistics and two-way ANOVA were employed. The results showed a significant main effect for contextual factors; participants' choice of requestive features was affected by the two social factors of power and distance. Proficiency, however, did not have a significant effect on the pragmatic performance of participants. The findings of this study showed pragmatic development of participants on the one hand and some evidence of their underdeveloped pragmatic performance on the other hand, which makes explicit instruction a necessity.