| 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, but Jack still wants nothing to do with his nephew. Soon after this encounter, for reasons unknown, 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, Kate is still carrying out a promise to Sawyer and Jack, who has become an alcoholic, berates her over it and ends their 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, acting on Ben's orders, calls her and asks her to meet him, with the intent 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. Kate has a revelation that she has only been holding on to Aaron out of her feelings for Sawyer and returns the boy to his grandmother. 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. She tells him they are not together. They, along with Hurley, crash onto the main island.
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