This study investigates the development of requests from the beginning of foreign language instruction to advanced levels of proficiency in face-toface interactions. Data were collected from three learner groups (American learners of Spanish) (45 learners [15 per group: beginning, intermediate, advanced]). Open role plays were used to collect data in four request situations. Data were analyzed for request head acts (direct, conventional indirect, non-conventional indirect), the request perspective, and internal and external modification. Findings indicate that the beginner group produced the largest number of direct requests. They, thus, showed little competence in situational variation. These direct requests were often realized by means of verbless requests, statements of need, imperatives, and requests with an infinitive used as a main verb. In contrast, a strong preference for conventionally indirect requests was observed among intermediate and advanced learners in formal and informal situations, with a decline in direct requests noted to appear with increasing proficiency. Four stages of pragmatic development among learners in a FL context were identified and discussed in light of existing research in pragmatic development. This study also addresses the issue of the primacy of pragmatics over grammar in expressing pragmatic intent, formula research in interlanguage pragmatics, and pragmatic development in the FL classroom.