I laughed the first time I saw this
difficult child 2 spent so much time with that monkey puppet of his, this just fit perfectly... Unfortunately, he still has that puppet and still talks to it. Fortunately, he now does this only in the privacy of his own apartment.
difficult child 1 was sort of like your difficult child, never wanted us to go anywhere without him, never let me out of his sight. However, by the time he was your difficult child's age, he didn't want me anywhere near him, unless he was manic, "bored." Then he would do everything and anything he could think of to get me angry. If he succeeded, he would smile, sort of an evil kind of smile - His cure for boredom. It used to drive me, as difficult child 2 would say, "bananas..."
I think, in time, your difficult child will grow out of this - At least I'm hoping he does! SFR