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Sportswriter P.J. Franklin continues her on-again, off-again search for romance as she joins her best friend, Stephanie, for a long-planned double date in Italy. The new season unfolds once the identity of P.J.’s mystery date is revealed and she returns to Chicago where her brother, Andy, has taken a high-paying job at a big corporate law firm and moved his family back into town from the suburbs. Change is in the air for the rest of P.J.’s poker pals, too: Bobby is getting married to Andy’s beautiful Swedish nanny, and Brendan must reinvent himself after losing his radio station job. And while Stephanie parlays her own disappointing vacation romance into a best-selling dating advice book, Kenny and Mike continue to look for love in the Windy City’s singles scene.