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Jack is unable to decide what to do next about his career and his life. Abby is livid when her boss hires her old flame. Meanwhile, Natalie struggles with her transition from "with-it" teen to "with-child" object of scandal at school. Also, Abby's hot under the collar after her former flame lands a job at the agency. Lastly, Cooper wins a national writing contest and attracts the attention of an older woman.