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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.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.Jules' relationship with Josh ends when he tells her that he loves her and Jules does not feel the same way.

Jules, however, tells him that she loves him but "not that way any more" and that their happy ending is them as friends, raising their son Travis (Dan Byrd) together.

Her relationship with Jeff ends when the relationship becomes too serious for Jules who is not looking for anything too serious so soon after her divorce, whereas Jeff is ready to settle down as he has been "playing the field" for a long time.

After her relationship with Jeff ends, Jules falls into bed with her ex-husband Bobby (Brian Van Holt).

Jules' best friend and neighbor Ellie tries to prevent her from going out while her son is constantly being embarrassed by both of his parents.

The show was originally about older women ("cougars") dating younger men, as Jules begins dating Josh (Nick Zano) and Barb is often seen "hunting".