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- Olivia and Jack consider the inevitable challenge of a long distance relationship as Jack begins his new job as chief editor in Seattle. But Jack soon finds himself at an impasse with his boss, who questions Jack's ability to meet his bottom line. Meanwhile, Paul is avoiding a second date with Alex, even as Olivia pressures him to take a chance on love. And as Will promises to shape up in hopes of starting fresh with his sister, his latest mishap proves Olivia was right all along.