The rapid development of messaging technologies has bridged the gap between teachers and learners and brought a new style in daily social interactions of the individuals, which promoted concerns about the matter of politeness in interacting via different means of communication. This study investigated the politeness strategies and the levels of (im)politeness in requests made by Iranian EFL learners via Telegram, email, and face-to-face interactions. It also investigated the gender differences via these channels of communication. To this end, 56 upper-intermediate EFL learners were randomly selected and their requests made via different means of communication were collected. The content of the requests was analyzed and coded as bald on-record, positive politeness, negative politeness, and off-record strategies. The (im)politeness level was rated as very impolite to over-polite. The data analysis procedure included counting the frequency, calculating the percentage, and a chi-square test. The results indicated that Iranian EFL learners tend to use the positive-politeness strategy more than the others. The findings also showed that the requests made via email were significantly more polite those made in Telegram or face-to-face interactions. The outcomes of the interview revealed that the learners tend to transfer Persian pragmatics in chatting via Telegram. The findings of this study could raise the awareness of EFL practitioners and learners and make them conscious in applying more appropriate strategies in their interactions.