@firefly,
Don't forget he purchased hundreds of dollars worth of lottery tickets and only gave up and started with the next course of action when he missed out on the $120 million.
In my opinion, he thought Money would solve everything, hence why any job mentioned was beneath him. "I drive a BMW, have cool sunglasses". He thought if he had money, he would have women.
He was in-deed ecstatic to learn his Mother was dating someone worth $500 million and wanted her to marry him. His Mother was the one that bought him the car.
I'm of the Opinion, his Father he had some respect or fear of. Maybe fear, as he didn't want to kill him, I believe he thought he couldn't take on his Father. Though he hated it he, the Father, stood up for his Step-Mother and he believed the house his Father owned, would one day be his, so he could walk into it at any time, without knocking because in his mind, he was rich, it was his.
I wonder if he used his Father in conversations and as that wasn't enough even to win a woman, he had to work out how to get his own money.
I believe he attended the Premiers etc, to try to make him social.
I have a feeling he didn't get much at all from his Father and Step-Mother including love.
He was happy to get a sibling at one stage and then, hated him. Like everyone else.
He wasn't against women, ultimately it was the blonde girl at a young age, then blondes full stop. He was against the World, the World owed him. He hated everyone.