R. Joshua ben Hananiah

What was the incident with the little boy? I was once on a journey when I noticed a little boy sitting at a crossroads. I asked him, "My son, by what road do we go to the town?" "This one," he replied, "is short but long, and that one is long but short." I proceeded along the "short but long" road. When I approached the town, I discovered that [the road became a dead end] because gardens and orchards blocked access to the town. I turned back and said to him, "My son, did you not tell me that this road was short?" He replied, "Did I not also tell you, 'But long'?" I kissed him on his head and said to him, "Happy are you, O Israel, for all of you, from the oldest to the youngest among you, are wise."

I am confused by this story. What is the point? A wise person would have answered the question civilly by saying this road goes there but it is long. This road leads to a dead end. Yet the boy is praised. Why?
Also , it raises questions about R. Joshua ben Hananiah. Why doesn't he ask for an explanation of the conundrum? He was willing to ask directions but not willing to admit he didn't understand a response.