I think Kevin doesn't really know how to fight or is afraid to. Maybe he felt embarrassed that this kid that wasn't bigger than him took his money and he wasn't able to brush the kid off. Some kids are that way.
As to the retainer, maybe he was also still upset over the first thing when he was crying so it was more serious to him. Also, maybe he felt since it was an expensive thing and he wanted to be responsible for it so as not to get his parents angry if he lost it and he was worried that that was going to happen. Gil does tell Karen to forget it but Karen mentions the money and that it is important. Maybe the dental insurance doesn't cover it.

It has nothing to do with being "smart enough to have anxiety issues".
You and your brothers are lucky. There are all sorts in this world.
"Fasten your seatbelts. It's going to be a bumpy night"

Some kids are more sensitive than others. Usually this is in kids who are a lot smarter and they are hard on themselves.
Sorry my brothers and I weren't smart enough to have anxiety issues.
Knock it off, Hudson.

I'm watching it now. It's anxiety and stress. Some kids are more sensitive than others. Usually this is in kids who are a lot smarter and they are hard on themselves. One my nephews is like this. He puts so much stress on himself for school. His parents don't force him either they tell him to relax and lighten up. But if he gets a B he is so angry at himself.
"The retainer costs about $200 in 1988/1989 money, which is the equivalent of $655-750 nowadays, but c'mon!!! Didn't Gil have Dental insurance for his family?!"

I wore something like a retainer for TMJ in the early 1990s. Insurance wouldn't cover accidents with it. My dogs go into a hold of my retainer not once but twice. My parents went crazy!!! I can't remember how much it cost but it was expensive. I remember freaking out like Kevin the second time I caught my dog with it. I knew my parents were going to hit the roof! I also remember my parents fighting and my dad screaming how insurance only covered it breaking due to it being worn and not accidents.
~For beautiful eyes look for the good in others, for beautiful lips speak only words of kindness~

Thanks so much, Novastar! I never thought it was an anxiety issue. I may need to see the film again. I don't agree with the Mom about his behavior centering around the fact that he's the first born. My eldest brother never acted like that. In fact, he is very laid back, even when he was a kid. I guess it effects kids differently.
Knock it off, Hudson.

I think he had an anxiety disorder, he couldn't handle anything, and I think the mom was right that it's because he's the first, parents freak out about every little thing with their first kid, and kids learn how to act in situations by how parents act, so he probably grew up seeing his parents freak out at everything, his dad especially because he does still have some of that, and it just stuck with him.