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With the help of the Cul-de-sac Crew, Grayson tricks Jules into being less predictable in her day-to-day life, but when she fails, Grayson is able to plan ahead and propose to her outside at night under a teepee'd tree.

The season follows the ups and downs of their engagement, including their many trips to a new psychiatrist (played by guest star Nicole Sullivan).

When Kirsten gets a job in Chicago, he proposes to her in an attempt to get her to stay, which she rejects.Laurie guilts Jules into letting her be Co-Maid of Honor (Co-Mo's! Travis gets into a skateboarding accident while being pulled by Dog Travis, and goes into the hospital.His injury causes him to wear a helmet for six episodes.Toward the end of the season, the simmering feelings between Jules and neighbor Grayson (Josh Hopkins) boil to the surface, and the two begin a relationship.The second season follows the development of Jules and Grayson's relationship.

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