When communicating, people adapt their linguistic representations to those of their interlocutors. Previous studies have shown that adaptation also works at the semantic level, with listeners aligning their interpretations of vague expressions such as quantifiers to those by a certain speaker. While adaptation has been found to arise by passive exposure to the interlocutor’s linguistic representations, we hypothesize that actively seeking information could boost this effect. In particular, asking clarification questions can be helpful to reduce the uncertainty about someone else’s interpretation. We focus on the gradable adjectives ‘big’ and ‘small’ and show that, in line with previous findings, speakers can align their representations to those by their interlocutors. Moreover, this effect is boosted when people are given the possibility to ask questions. Though participants can generally ask for useful information, we observe that this ability improves as the interaction progresses.