Just at the point where Harold believes himself to be going mad, he seeks advice from a psychiatrist, (played with a squint of suspicion by Linda Hunt), who listens patiently to his ravings and refers him on to a professor of literature, Dr Jules Hilbert (Dustin Hoffman), a man as spontaneous and emotional and strung out on caffeine as Harold is ordered and subdued. Hilbert also listens, while slurping constantly from his coffee mug, explaining to Harold that whatever story he believes himself to be a part of can only be resolved through one of a number of standard literary archetypes. Patient questioning comes up with a handul of names of authors who could be transcribing his life, eventually leading the duo to one writer, Kay Eiffel (Emma Thompson), simply because all of her published novels end in the death of the main character.
It’s a good deduction, Eiffel is indeed the writer, a fact confirmed when Harold hears her speaking on an old television show, but she has problems of her own. She hasn’t published anything in a decade, and is terminally blocked, writing and rewriting the last couple of chapters of Harold’s life without being able to find a way to conclude her story satisfactorily. To that end, her publishers have sent her an assistant (played with restraint by Queen Latifah), a no-nonsense woman who quickly takes the neurotic, chain-smoking, suicidal author in hand and attaches her to a routine. Meanwhile, something extraordinary has happened to Harold. His apartment has been destroyed in an accident, forcing him to move in with his only friend Dave (played by Tony Hale from Arrested Development). While dealing with this spur of disorder, he goes to meet a woman who has misfiled her tax return, and falls in love with her. Ana, a free-spirited, heavily tattooed baker (played with a heartbreaking sincerity by Maggie Gyllenhaal) initially despises this government enforcer, rifling through her papers in an effort to prosecute her, but gradually softens, until a point where the two stand before one another, mutually smitten, and suddenly alive again. But the voice is telling Harold his time is running out, with his life being taken from him just at the point where it has become worth living.