Alex Sheldon (LUKE WILSON) is an author with a sticky problem. Not only is he broke, but he also owes $100,000 to some Cuban mafia figures following some bad gambling choices. He does have a way to come up with the money - by delivering his next novel to Wirschafter (ROB REINER), his publisher
- but a serious case of writer's block has stymied his effort.
When one of the mob thugs torches his laptop computer, Alex hires stenographer Emma Dinsmore (KATE HUDSON) to take down his dictation. She's initially reluctant to accept the job, especially when she learns that if Alex doesn't get the money in 30 days he'll be dead, but eventually agrees to the job.
Alex then slowly starts to reveal his novel about Adam Shipley (LUKE WILSON), a 1920s era writer who's been hired to tutor the children of Polina Delacroix (SOPHIE MARCEAU), a lovely French woman who's in dire financial straits. Unless her wealthy grandmother dies and leaves Polina her inheritance, she'll have to marry her wealthy suitor, John Shaw (DAVID PAYMER).
The only problem is that Adam is instantly smitten with Polina and tries to figure out how to compete with Shaw for her affection. Along the way, he also finds himself attracted to her au pair, who changes from Ylva to Elsa to Eldora and finally to Anna (all KATE HUDSON).
With time running out and Emma having no problem throwing in her two cents regarding every writing decision he makes, Alex must race to finish the novel, all while finding himself falling for Emma and vice-versa.