"Do you really think I'm good at this?"
"I'm the one who saved you."
"Who in the world am I?"
One of my favorite flashbacks/flashforwards of the entire series has some of the most telling quotes from our fearless leader, Jack Shephard. These three capture the mindset of post-island Jack; they encapsulate his uncertainty, insecurity, and hero complex that will drive him to the depths of despair and eventually lead him back to the island.
The scene that really stuck out to me the most this time through was when Jack wakes Kate up in the middle of the night to propose. First, he asks her if she really thinks he's good at this, at being a loving father and stable mate, two things about which Jack holds tremendous doubt. The former comes from his father (who appropriately haunts him in this very episode), the latter from his failed marriage with Sarah. When Kate says she does, he proposes. She happily accepts.
The expression on Jack's face as he hugs Kate is not only one of joy, but one of accomplishment, like he finally has the woman he's been after since she stitched him up on the beach. It's a lot like the look on his face as defiantly he calls the freighter in Through the Looking Glass. He's on top of the world. But is that really what you should feel when you get engaged? Happiness, yes, but is it really the same as achieving a goal? Is he trying to prove something here? Of course he is. Jack is always trying to prove something, where it's to his father, Ben, Sawyer, Kate, or himself. Kate has always looked to Jack as a hero, someone good. Jack knows this. When she accepts his engagement, Jack sees it as an affirmation from Kate of everything he did as a leader of the survivors. He rescued her from the island and he has earned her respect as a father. It satisfies his hero complex, and for a brief moment it looks like Jack might have put his demons to rest.
It all quickly crumbles when he sees his father in the lobby of the hospital. Not only does he think he's going crazy, but it's a symbol that his insecurities stemming from his relationship with his father are not dead and buried. Jack never thinks he can live up to his father's expectations for him, and seeing him in at the hospital reminds him of that and the island where his body is supposed to be. The question remains - how the hell is Christian Shephard appearing to Jack at all? Is it Jacob? Is it the Man in Black? Is it something else entirely? Either way, it's clear Jack takes this as the first sign that leaving the island might not have been the right thing thing to do.
When Jack comes home to Kate talking on the phone late at night, his trust issues begin to emerge as well. An under-discussed part of Jack's character is his issue with trust, and it's twice as bad with women he cares for than anyone else (see Tale of Two Cities). And Kate, who has undermined that trust on several occasions, is especially vulnerable to incurring his distrustful wrath. Coupled with his visions of his father, and there's a recipe for disaster. Now bad Jack starts pouring out. The drinking. The suspicions. The chest-thumping. He's jealous of Sawyer even though they're separated by 30 years and thousands of miles. After all this, his relationship with Kate is never the same. Somehow this leads to him blowing up an atomic bomb, but that's a little ways off still.
Jack's encounters with his father and with Hurley start to sow the seeds of doubt about whether leaving the island was really the right thing to do. How can his father be walking around if his dead body should be somewhere on that island? How is Charlie talking to Hurley, and actually giving him poignant advice? The transition to a man of faith begins in this episode. He just doesn't know it yet.
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