Two Dutch directional prepositions (i.e., naar and richting) provide a useful paradigm to study endpoint conceptualization. Experiment 1 adopted a sentence comprehension task and confirmed the linguistic proposal that, when naar was used in motion event descriptions, participants were more certain that the reference object was the goal of the agent than when richting was used. Experiment 2 and Experiment 3 used this linguistic pair to test the effect of two factors (i.e., the actor's goal and the interlocutor's status) on endpoint conceptualization via language production tasks. We found significant effects of both factors. First, participants chose naar more often when there was an inference in the referential situation that the reference object was the actor's goal than when there was no such inference. Second, participants chose richting more often when they were told to describe the referential scenario to a police officer than to a friend. Participants were more cautious with their statements and were less willing to commit themselves to stating the goal of the agent when talking to a police officer than to a friend. The results are discussed in relation to relevant linguistic theories and event theories.