Jake tries to cleanse himself of painful memories of his former fiancée, Annie (Charlotte Ross), only to have her turn up on his doorstep to retrieve a family watch she gave him before they broke up. Elsewhere, Naomi is overwhelmed with being a new mother and leans on Jake for support.
Jake's assigned to work with his ex-fiancée, Annie, on a publicity campaign for the governor's autobiography, which sparks old issues. Gov. Reynolds: Dakin Matthews. Mrs. Reynolds: Amanda Carlin. Annie: Charlotte Ross.
Jake's college friend Mark reappears after a divorce, looking for tips on getting back into the singles scene. Elsewhere, Jake's attempts to forget about Annie are frustrated by the fact that she keeps calling him. Mark: Dondre Whitfield. Annie: Charlotte Ross.