This study attempts to investigate the pragmalinguistic and sociopragmatic development of Iranian EFL learners cross-sectionally when making requests in different situations. To this end, 103 university students in three proficiency levels of pre-intermediate, upperintermediate, and advanced were asked to write three discourse completion tests (DCTs) of requests in different situations with various social and power relation demands and 20% of them were interviewed about their DCTs. The analyses of these written and verbal reports suggested that parallel with proficiency there was a movement from directness to conventional indirectness and an expansion of the repertoire of both external and internal modification devices. Even though all the participants expressed their awareness of the sociopragmatic requirements of different request situations in their verbal reports increasing proficiency led to the application of this awareness in practice. That is, advanced learners were more successful to differentiate among the situations both sociopragmatically and pragmalinguistically. The results are discussed in light of previous research and available developmental patterns.