This paper examines the language of requests among the hotel trainees in Jordan. It seeks to explore the ways in which the trainees employ requestive strategies at the service counter in managing interpersonal and cross-cultural communication. Specifically, it discusses the Jordanian trainees' use of imperative requests compared with native speakers hotel staff and relates any divergences to politeness and cultural factors. The data collected include conversations between the trainees and hotel guests. The findings demonstrate that trainees rely more on imperative constructions and they favour conventional imperatives more than any other types. The findings also reveal that the trainees deviate from the native speakers' performance in terms of volume and types of strategies used. Some of these deviations may be due to Arabic language influence, pragmalinguistic and sociopragmatic transfer or to insufficient linguistic and pragmatic competences.