Emma (Kate Hudson) is a chic twenty-something trying to make her way as a stenographer in Boston. Alex (Luke Wilson) is a brilliant author whose computer is destroyed by the pair of Cuban criminals coming to collect the $100,000 he owes them. So naturally, instead of buying a new one, he thinks, why not hire a stenographer?

So Alex places a false ad to lure in Emma's much needed talents. His charm and desperation convince her that he's a shady pervert--it is only when he becomes proud and aggressive that she feels sorry for him and offers him her services. Professional services, of course.

The two embark on the arduous journey of writing a bestseller novel within 30 days. Alex dictates; Emma transcribes, although remains skeptical of Alex's 'genius'. While Alex tries to spell out his theoretical progression of love, Emma challenges him at every turn, arguing that his fictitious rendition is an impossible reality. At first aggravated by her invasive two cents, he becomes fond of her smart and witty demeanor, and her practical and blunt stabs of reality.

The production becomes a story within a story, recycling actors from the "real life" of the movie to ones who act out the storyline of Alex's novel. Producer/Director Rob Reiner squeezes in some quirky jokes and clich‚ advice-- "People get hurt in books, people get hurt in reality." Thanks, Captain Obvious. With more dialog than action, the ornate script fails to bring life to the show on screen. In the end, Alex and Emma's relationship exposes a vulnerable girl corrupted by an insensitive guy, struggling to find his own happiness while making mistakes at her expense. It portrays the frustrated reader troubled by the author in control, who evades reality with glimpses of perfection.

The film develops the image of imperfect love, inadequate lovers, and desperate happiness as Alex and Emma find solace by settling for each other. Meanwhile, the audience is left with a lingering question--why didn't Alex just get another laptop?