That was Socrates' point. He was asking questions to expose how brittle the claims of knowledge and certainty were. I do find it strange that Wittgenstein—a man who considered Kierkegaard (who wrote an entire book on irony and Socrates) as one of his favorite thinkers—seems not to have realized that Socrates' quest for a certain, clear meaning of a team was ironically intended to always finish unresolved. It makes me a bit curious what he took from Kierkegaard, who was every bit as much of an ironist, if Plato's rather blunt representations of Socratic irony alluded him.
Of course the irony is that Wittgenstein asks "why?" again and again like Socrates and for very much the same purpose (to show that it gets us caught in circles), thus representing even more ironic loops than the previous circles. Wittgenstein turns to philosophy to repudiate it and show as much to his students (show the fly out of the bottle), but in so doing he affirms a central Socratic lesson, but with far less irony. And I would say irony wins out: rather than quiet philosophy into therapy, Wittgenstein became the most influential 20th century philosopher who attracts by far the most published academic and popular commentary.