The movie is a masterpiece, and I saw so much in it during this latest viewing that I haven't seen before. The desperation of Will - the fear that no one can be trusted; that anything could go wrong and that it isn't worth a risk. Touching moments, like his buddies getting him a car. In that moment, all the jokes were dropped. For that moment, the faux masculinity and juvenile attitudes subsided to a true moment when friends acknowledged their friend's birthday, and let their friendship show without pretense.
Sean evolved through the movie, most directly shown by his taking a sabbatical. But I noticed something else - a smaller detail, though I won't say I'm the first to hear it. Throughout, Sean calls Will nicknames - Chief, Sport - and even as I type this, I realize it might be allusions to Will's arrogance (Chief) or his smart-alleck nature. At the end of the movie, Sean sends Will off with "Hey, good luck, Son."
Sean's message to Will, that he finally learns, is that you have to do what is right for you.
Skylar and Will have excellent chemistry; their relationship seemed very genuine and fraught. Their discussion of her move to California and the ensuing argument was an incredible performance.
We don't have to stop growing. Don't be afraid to put some chips on the table.