On the verge of a mid-life crisis, a former stand-up comedian believes an appearance on a popular late-night show will save his career, but ends up learning the journey is more rewarding than the destination.

In the glamorous world of New York City, Rebecca Bloomwood is a fun-loving girl who is really good at shopping – a little too good, perhaps. She dreams of working for her favorite fashion magazine, but can't quite get her foot in the door – until ironically, she snags a job as an advice columnist for a financial magazine published by the same company.