Shy or Rude, Part II

Question

I have a follow-up question for you on the subject of how to deal with shyness. You have previously answered questions on the subject in "Shyness."
Our three and a half year old son is an extremely well-behaved and sweet child (partially because of his nature, partially because of our "old-fashioned" parenting philosophy). Unfortunately, he is also very shy, and mostly refuses to speak to or even look at people we see out in public (as was the case in the two messages I referenced above). He also will often times have little to do with favorite friends and relatives who come over to our house - he will sometimes just wander off to his room, or just bury his face in the couch and pretend they aren't there. In a very few instances, he has actually become rude, glaring at people, pouting, and answering questions with hateful-sounding "Yeah" and "No" answers.
As with most oldest children, he is fairly compliant and eager-to-please in most situations, but he definitely has a strong stubborn streak and sometimes insists on getting burned a few times before he will accept that the fire is hot, so to speak.
I have finally just had it. Yesterday, we were in a store and he refused to speak to or look at a woman who worked there and asked him a question. Even after I pulled him aside and reminded him that he was not being nice, etc., he refused to be even somewhat polite. So when we got in the car, I told him (in a very calm, matter-of-fact manner) that as a result of his behavior, he would not be getting dessert that night after dinner.
My wife, a former first-grade teacher with a degree in early childhood development, feels that this is too harsh and that punishment is just going to traumatize him in social situations even more than he already is. I feel that this is purely a behavior issue and that even at three and a half, he should at least be able to be polite to people, especially ones he already knows.
By the way, we have tried the "role playing" exercises, but he just clams up and refuses to go along - whether this is caused by defiance or anxiety is anyone's guess.
One last thing I will mention: he loves Oscar the Grouch, Sesame Street's infamous anti-social trash can inhabitant. Not that our son is trying to act like Oscar - when he plays with a stuffed Oscar toy we gave him a year or so ago, we can overhear Oscar suddenly saying "Please" and "Thank you", and playing with our son's other stuffed animals in relative peace. But there is something about Oscar that definitely appeals to him, as that has been his favorite character for over a year now.

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