| Relationship: Pairing (Formerly engaged)
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| Dealt with in episodes: "Through the Looking Glass", "Eggtown", "Something Nice Back Home", "There's No Place Like Home, Parts 2 & 3", "The Little Prince", "This Place Is Death", "316"
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| Details: Jack and Kate, off the island, continue to draw closer together. On the Searcher, Jack asks Kate if she's "with him" when he needs to present the lie to the rest of the Oceanic Six. She responds that she's "always been with him." Shortly after, however, the two have a fallout, presumably over Aaron. They are reunited when Jack agrees to testify as a character witness during Kate's murder trial. Though denies it to the prosecution, he admits that he still loves her. Kate is pleased and invites him over for a visit. He declines, but she leaves the door open for him, telling him that should he change his mind about Aaron, he can visit them anytime. Soon after this encounter, Jack decides to take Kate up on her offer and he and Kate engage in an established relationship, living together with Aaron. He asks Kate to marry him, and she says yes. However, due to his own insecurities and and guilt, Jack ends the relationship. He becomes a despondent man who is addicted to alcohol and painkillers. When she finally agrees to meet him at the airport, Kate is struck by his disheveled state. Jack tries to convince Kate that they must return to the island, to which she disagrees, and she angrily tells Jack that she does not want to go back to the island. Upset and furious, she drives away. Two days later, Jack, concerned for her and Aaron's safety, calls her and asks her to meet him, with the intent to keep them safe, and to convince her to go back to the island. But she becomes upset with Jack, once again, when she believes he only pretended to care about her to get her to go back. The next night, Jack goes home to find Kate in his apartment, depressed. She tells him that she will go back to the island with him if he promises not to ask about Aaron, and then kisses him. They have sex. The next morning, she is distant towards him, but agrees to meet him at the airport. They, along with Hurley, crash onto the main island.
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