Struggling with her debilitating obsession with shopping and the sudden collapse of her income source, Rebecca Bloomwood (Isla Fisher) unintentionally lands a job writing for a financial magazine after a drunken letter-mailing mix-up. Ironically writing about the consumer caution of which she has not abided, Rebecca's innovative comparisons and unconventional metaphors for economics grants her critical acclaim, public success, and the admiration of her supportive boss Luke Brandon (Hugh Dancy). But as she draws closer to her ultimate goal of writing for renowned fashion magazine Alette, she questions her true ambitions and must determine if overcoming her "shopaholic" condition will bring her real happiness.

Cheery Alex Fletcher lives comfortably in Manhattan off the residuals from his 80's pop success and reprising his hits at school reunions, theme parks, and state fairs. But those gigs are declining, so he jumps at the chance to write a song and record it with reigning teen idol Cora Corman. Trouble is, he's good at melodies but needs a lyricist and has less than a week to finish. Enter Sophie Fisher, subbing for a friend who waters Alex's plants; she's a pretty good poet, quick witted, and could do it, if she'd agree. But there's some sort of shadow over her head that Alex may not be able to charm his way past. And what if they do get a song written, what then?

Because of his extreme wealth and suave good looks, Edward Lewis could seemingly have any woman he wants, that committed significant other which he needs on his arm at social events to further how he makes his money as a corporate raider. However, he focuses more on his corporate raiding pursuits with his partner in crime, Philip Stuckey, his lawyer of ten years, than those women, with every significant other he's had in his life feeling neglected and eventually leaving him, this fact about which he is just coming to the realization. In Beverly Hills, Edward, in needing that woman on his arms as he and Philip work toward taking over the company owned by the increasingly insolvent James Morse, decides, based on a chance encounter, to hire Hollywood Boulevard hooker Vivian Ward as his escort for the week 24/7. He does so because he wants to have a professional who would be committed to the work, yet not have any commitments to her after the week is over. Beyond their chance encounter, he also makes this decision because she surprises him about how unhookerish she is in certain respects. Vivian, relatively new to Los Angeles and the business, still has to look and act the part, with Edward, beyond giving her money, leaving her largely to her own devices to do so. So she gets a somewhat unlikely Henry Higgins in Barney Thompson, the manager of the Beverly Wilshire Hotel where Edward is staying. Barney has to draw that fine line of keeping the hotel's upscale clients happy, while maintaining the posh decorum of the upper class, which does not include people coming into the hotel looking for rooms with hourly rates. As Barney and his associates are able to transform Vivian into a Cinderella, the questions become whether Vivian can go back to her Hollywood Boulevard life and whether she does have her Prince Charming beyond this week in the form of Edward or anyone else who truly does see her as Cinderella as opposed to a Hollywood Boulevard streetwalker.