Aided by technology, people are increasingly able to communicate across geographical, cultural, and language barriers. This ability also results in new challenges, as interlocutors need to adapt their communication approaches to increasingly diverse circumstances. In this work, we take the first steps towards automatically assisting people in adjusting their language to a specific communication circumstance. As a case study, we focus on facilitating the accurate transmission of pragmatic intentions and introduce a methodology for suggesting paraphrases that achieve the intended level of politeness under a given communication circumstance. We demonstrate the feasibility of this approach by evaluating our method in two realistic communication scenarios and show that it can reduce the potential for misalignment between the speaker’s intentions and the listener’s perceptions in both cases.