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.

Widow Jean Miller thinks she's ready for a new romance with her high school sweetheart, Sam Morrissey, a physician of considerable means. The only thing standing in the way of rekindling this first love is the presence of his very attractive, very together 39-year-old girlfriend, Claire.