This inquiry explores pragmatic acquisition of requests for English-speaking learners of Spanish. It expands upon former work by examining the acquisition of second language requests during a short-term immersion program (6 weeks) in Madrid, Spain and in three situational contexts: food and drink, general merchandise, and familial. Data were gathered employing an experimental computerized oral discourse completion task. Requests made by learners (501 requests) and native speakers (224 requests) were compared considering personal deictic orientation and directness of the requests. For learners, shifts from speaker-oriented to hearer-oriented requests pointed out greater pragmatic development in food and drink and familial contexts. Results are debated considering pragmatic developmental stages and differential results in the three contexts.