The proverb "chalepa ta kala" ("fine things are difficult") is invoked in three dialogues in the Platonic corpus: "Hippias Major," "Cratylus" and "Republic." In this paper, I argue that the context in which the proverb arises reveals Socrates' considerable pedagogical dexterity as he uses the proverb to rebuke his interlocutor in one dialogue but to encourage his interlocutors in another. In the third, he gauges his interlocutors' mention of the proverb to be indicative of their preparedness for a more difficult philosophical trial. What emerges in the study of these three Platonic dialogues is that Socrates believes that how he and others "describe" learning makes a tangible difference in philosophical investigation.