A/N: I just read some critique of Jess being a rude and careless rebel and I have this thing that I try to find an excuse for his behaviour in every situation, even if it's far from perfect. So this came to life. Just a bit of Jess-analysis.
Disclaimer: The Gilmore Girls are not mine. Nor is Jess. He would have had a better childhood if I had any say in it. Even if I was the one who put some awful things in this story.
Jess Mariano had no respect for his elders.
It was a fact widely known, somewhat accepted and never questioned.
A random adult who had the misfortune of encountering him never pondered on the reasons for his attitude, only escaped from his surly presence and attempted to forget all about the awful boy. Sometimes it was because they were afraid of him. Of the dark cloud he seemed to carry above his head.
Of course, ignoring ugly matters and pretending they don't exist is the way to go, it always has been.
Even for the nice social workers in tweed skirts and lipsticks perfectly matching their complexion who visited him and his mother once in a while in New York. They smiled insincerely at him while he refused to look up at them from the book he was pretending to read. They didn't dare disturb such a genius child and didn't come close enough to see the bruises on his arms or the red marks on his buttocks left by a belt of one of Liz's boyfriends. He would kick and bite before letting anyone see all that anyway.
His mother herself was often oblivious. Sometimes it relieved him. Sometimes he hated her for it. And when the anger faded he still wasn't able to respect her like a son should respect a mother. He returned her indifference with his own and when she went through her occasional phases of going all maternal on him ("Baby, when did you grow so tall, we have to go shopping for some clothes for you soon!"), he just shot her unreadable looks, knowing that there would be a new guy soon and she would have someone else to focus on.
He discovered quite early on that grown-ups were only nice to him to free their conscious from guilt.
That made him feel insignificant. He was a nobody. He couldn't respect the grown-ups (were they really?) around him before he gained some resemblance of self-respect first. It wasn't easy, knowing that his body was too weak to defend Liz from the rage of Bobby or himself from Mark's wandering hands. And he wasn't even able to talk Liz out of bringing home guys she knew nothing about. For her every newly met man provided hope. For Jess - usually fear and disgust.
By the time he was seventeen he wasn't scared anymore. He learned to fight (he wasn't that strong but he was fast and had good technique) and he knew full well he had an intellectual advantage over most of the adults he crossed paths with.
The fear disappeared but the lack of respect remained. They all seemed hypocritical to him.
That view changed a bit when he moved to Stars Hollow to live with his uncle. Luke was a loser. But he was a new kind of a loser. An altruistic loser. He had impossible demands (he demanded that Jess started caring, not knowing that his nephew tried his best not to care since the day of his fifth birthday of which his mother forgot) but his concern was genuine and Jess appreciated it. He wasn't able to show it on a regular basis, he was too reserved still, but he did quit smoking and he did fix the toaster. He even gave his uncle advice on women (partly for his own entertainment).
Everyone yammered on and on about how he had authority issues, not realising that the authority he was met with until well into his teenage years was always perverted in one way or another.
They all judged him, so he judged them too. He judged them not worthy of his time that could be spent with infinitely better fictional characters.
He just... he just couldn't be bothered.
So he poured them coffee carelessly, growling at them occasionally and persuading to himself that it was for the best.
It wasn't about being cool (although that was a perk, too).
It was about being impossible to hurt.