Woody Analysis:

Also discussed recently is the view that Woody has lived his life doing what he ‘thought’ he was supposed to do (being responsible, taking care of his brother, getting a responsible job, falling for a girl, and wanting to get married and have kids and live that perfect ‘American Dream’.) Living by how he thinks the world expects him to live.

Woody has (up to this season) been the 'good boy’. He's followed the fairytale life that we're all supposed to lead. And that fairytale wasn't shattered until JPF. Then his life suddenly changed. He went to the opposite spectrum of someone who's trying to not be who he believes the world thinks he should be. The point: He’s living his life by someone else’s rules/standards. He's got to learn to do things because it's what he wants.

What's interesting I find is that that moment in JPF didn't just change Woody it changed Jordan's life as well.

Think about it. The two have always been at opposite spectrums. Woody searching for the perfect life, Jordan running from it. Suddenly Woody gets shot and Jordan realizes (or at least is clued in) to HOW important Woody is to her. (And yes I do believe Jordan has feelings for Woody that are MORE than JUST friends.)

Suddenly Jordan is ready to take down some of those walls she's built around her and at the same time Woody puts up those walls. Is it because he's decided he's finished living the life he's supposed to live? 

Maybe what has to happen is Woody needs to come to terms with being HIMSELF. Not who he thinks he's supposed to be and not the person he knows he's NOT supposed to be. I think if he figures out what HE WANTS and not what the rest of the world expects of him, he might even out and he and Jordan could have a chance.

Word Association: “You’re going to drive yourself crazy. Not everything has to be so complicated.”

I think this quote speaks VOLUMES.  Woody is a bit lost. He can’t find a black and white answer/solution to his problem. And the thing is (as Lu said) sometimes there's isn't a RIGHT or WRONG.  Woody is still trying to see things in black and white. The big question is can he accept that "blue" is just as okay as "white".

Until he comes to terms that 'blue' is just as acceptable an answer as 'white' I don't think he's going to be happy. He's needs to start doing things for himself and not for the rest of the world or by the rules of the rest of the world.  And until he does that I don't think he'll be happy, even IF he had Jordan. 

Please Note: Snarky first posted about Woody being the 'good boy' to 'bad boy' theory.  I've just taken it and added my thoughts and opinions on the matter.  I agree with her initial analysis.