According to a commonly shared view, it is morally better (or less bad) to mislead a person, rather than lie to them. In recent times, this view was extensively criticised by Bernard Williams und Jennifer Saul, who argue that our moral preference for misleading is mistaken, and cannot be maintained after a closer consideration. In contrary to that, I try to show in the first part of this essay that there are some cases, in which we have moral reasons to mislead instead of lying. My focus is on an expressive and relationship-oriented analysis of misleading: The central thesis is that when we mislead somebody instead of lying to them, there are at least some cases, in which we thereby show that we respect the other person and very much want to maintain a trustful relationship. However, in the second part I demonstrate that the moral preference for misleading is not justified in all cases. There are two reasons for that: Firstly, the respect for a person shown through misleading instead of lying is not always appropriate. Secondly, it is not in all situations possible to show respect and interest in maintaining a trustful relationship through misleading instead of lying.