It's 1994 and Ollie Trinke (BEN AFFLECK) is on top of the world. Not only is he a wildly successful Manhattan music publicist, but he also has a beautiful girlfriend in Gertrude Steiney (JENNIFER LOPEZ). Things seem to be going their way when they're married and then find themselves expecting their first child.
Yet, a complication during labor leaves Ollie all alone to raise his young girl, Gertie. As a result, he moves in with his widowed father, Bart (GEORGE CARLIN), hoping he'll watch his granddaughter while Ollie continues to work. The resultant strain of trying to balance his personal and professional life eventually leads to an outburst that not only gets him fired, but also essentially leaves him blackballed in the industry, much to the dismay of his assistant, Arthur Brickman (JASON BIGGS).
Seven years later, Gertie (RAQUEL CASTRO) is a precious, little elementary school student while Ollie now works with Bart and his two friends, Greenie (STEPHEN ROOT) and Block (MIKE STAR), in the city's public works department. He isn't happy, however, since he still longs to return to his old field and has yet to reenter the dating world.
At a chance stop at the local video store, he and Gertie meet graduate student Maya (LIV TYLER) who takes an immediate interest in Ollie and his situation. The two dance between friendship and romance and Ollie finally begins to accept who and what he is. When a potential job comes his way, however, he must decide where his priorities, heart and best judgment lie.