"I look cool / Do I look chubby in this jacket?"

My kindergartner always tells me when he gets in trouble at school, which is pretty rare, and also when other kids get in trouble, which is good because we have an idea of who we don't want him to hang out with, and it's setting a good precedent for the future, when the kinds of trouble kids are getting in is less cute or innocuous.
So he starts telling us about one kid that we know gets in trouble, who his teacher in fact has decided to not let our boy sit with because he prompted my son to tell some girl that she's not pretty. Which was the only time he's really gotten into trouble.
Anyway he's telling me how this kid called him poopy-something or other and pushed him. I ask if he told the teacher, he says yes but it was clean up time so the teacher didn't do anything about it. To get the whole story from young children you have to ask them the same question a few times often in different ways because they don't necessarily understand what information you are trying to get out of them. So I again ask why did he call you names, and my son answers, "Okay I'm looking in the mirror saying, 'I look cool' (as he reenacts smiling and pointing at himself in the mirror) and then he called me a poopy-head and I didn't stop looking in the mirror, then he pushed me."
Oh, I understand now.

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My son has a cool Timberland jacket that he's been wearing since the weather has finally begun to cool off, so while we are driving to school today he asks me, "What does chubby mean?" so I tell him it means a little overweight, a little fat, but knowing that a question asked never comes from nowhere I ask him why does he want to know. He's like I just want to know, and I tell him it's okay to tell me, did he see something on TV, or did a kid at school call someone chubby?
He answers, "Okay, do I look chubby in this jacket?"
Me, "No! did someone tell you that, you're the least chubby person in our family." (He's lucked into a thin yet muscular physique)
Him, "Who's chubby in our family?"
2 1/2 year old son yells his own name in response to the who's chubby question, which is slightly true.
Me, "No one's chubby, but you're totally not chubby at all."
5 year-old, "No not me, I mean the jacket, do I LOOK chubby in the jacket?"
Me, "No you don't, your jacket is cool."
Him, "Okay."