Lucy Kelson (SANDRA BULLOCK) is a single lawyer who inherited her community activist mindset from her ultra-liberal parents Ruth (DANA IVEY) and Larry (ROBERT KLEIN). Accordingly, she isn't above trying to prevent the demolition of various landmark buildings in New York with her friends, Meryl (HEATHER BURNS) and Tom (JONATHAN DOKUCHITZ), although their actions are unsuccessful and land them in jail.
Once out, Lucy is determined to confront millionaire developer George Wade (HUGH GRANT) and give him a peace of her mind. A selfish but good-natured playboy who really lets his brother Howard (DAVID HAIG) run most of the business, George needs a new Chief Counsel and decides on the spot that Lucy would be perfect for the job.
She's naturally hesitant as he's the antithesis of everything she believes in, but his lucrative offer and promise not to tear down the Long Island Community Center changes her mind. Besides, she'll also have his company's resources at her disposal to help other charitable causes.
Yet, George is more interested in her decision-making regarding what are otherwise trivial matters in his life and eventually treats her like his personal assistant. She puts up with that for a rather long while, but eventually becomes fed up and announces her two weeks notice.
He's shocked and dismayed as he's come to rely on her tastes and opinions, but she proceeds to interview various potential replacements for her job, including June Carter (ALICIA WITT) who's fresh out of law school. As the days count down toward her departure, Lucy and George soon realize that terminating their relationship where they've grown to know each other so well might not be the best thing for either or both of them.