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Jimmy navigates the realities of being in a real relationship, while Gerald and Vanessa try to find work/life balance.
Jimmy finds himself out of his element when he falls for a stunning, powerhouse CEO who always manages to be one step ahead of him.
When Jimmy has trouble admitting that he's 51, he throws himself a second 50th birthday party. The party triggers flashbacks of where he was a year ago, showing Jimmy what a difference his family has made in his life.