Tales from the other side of the stethoscope: The trials of raising a "shy" kid

I hate to use the word "shy" - I try to not use it around him for fear he will label himself as such, but there is no getting around it: Noah is shy. It has its challenges, but for the most part shyness is easy to overcome by providing some extra time for him to warm up to the situation.

However, Halloween was a struggle.

In this respect, Noah reminded me of my brother (who has always hated getting dressed up for Halloween). We had to force Noah into his Halloween costume, he really didn't want to wear it. It was as if he was embarrassed to be wearing something out of the ordinary. I felt terrible about it (no matter how cute he looked). We got Layla dressed up too, with hopes that he would see that it is normal to wear a costume on this day! We had to force him out the door and I literally carried him door to door (he didn't refuse so long as he was being carried). When someone would open their door, he would cast his eyes down and pout. We just made him go to the neighbours around us, because they like to see the kids dressed up. When we got home, I felt terrible for forcing him to do something he clearly didn't want to do!

So I ask you: what do you do? With Noah, he is shy to try new things, but that doesn't mean that he won't like it eventually. Kindergym is one of his favourite activities - at first he clung to Keith for the whole class; now he is comfortable and has a great time. How would we know if he likes something if we don't get passed his initial hesitancy?

As Noah grows, we will have to respect his wishes for not wanting to go Trick or Treating, but that will come with challenges too, as he wonders why he can't eat his sister's candy (as I am sure Layla will love Halloween - she was smiling at everyone in her costume yesterday!)

We really hate making Noah so upset in these situations but we have to try to see if he really hates it or if it is just because it is a new experience. I suspect the need to wear a costume is even further incentive for him to hate Halloween though...