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Requests have been one of the most well-researched speech act realization studies as a research target. Most research, however, has been conducted on a comparison of native/non-native speakers' production, and very few studies have investigated the development of pragmatic competence. The present study examines a development of pragmatic competence in terms of the use of syntactic and lexical downgraders by Japanese EFL learners in order to mitigate requests to listeners of higher/equal status and with different psychological distance in high imposition situations. Their request realizations were measured by using a Discourse Completion Test. Then, using a series of ANOVA tests, the relationships between learners' use of syntactic and lexical downgraders, their grammatical competence, and time spent in an English-speaking environment, were analyzed. In general, the learners demonstrated the ability to use appropriate syntactical downgrading but an inability to use appropriate lexical downgrading. As a result, time of residency in an English-speaking environment and grammatical competence appeared to have positive effects on their ability to use appropriate downgrading in the situations analyzed in the present study. Reasons for this are discussed along with suggestions as to how instruction might improve acquisition of mitigation forms.