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When the goal is to keep someone from learning the truth, the rational way to behave in a conversation would be to say nothing at all or something completely irrelevant. But is this indeed what people do in such a situation? This thesis argues that instead of remaining silent or being non-informative, people instead revert to telling so-called half-truths (Vincent & Castelfranchi, 1982) through which they trick their listeners into making wrong inferences. People have the extraordinary gift to understand more than is literally being said in conversations. This is because conversational partners usually adhere to what is called the Cooperative Principle (Grice, 1975), which ensures that what we say is truthful, concise, relevant and perspicuous. Because a listener assumes that a speaker is adhering to this principle, she can make inferences regarding the underlying meaning of the speaker’s utterance. However, all of these assumptions can easily be abused by those who intend to deceive others. In a first study, we established that people indeed prefer misleading to lying. From a rational model analysis, we derived that the trust relationship between conversational partners is of crucial importance in deciding whether to be uninformative or misleading. In the next two studies, we manipulated this factor and looked at whether this caused them to give more misleading or non-informative answers. In addition to this we also tested whether the level of informativity of the misleading answer (i.e. how many options it excludes) has an effect on which strategy is preferred. The results clearly indicated that people prefer misleading to lying, and that the misleading answers were significantly more popular when they excluded fewer options and were thus less informative. However, the results regarding the trust relationship and type of answer were not so clear.