Peter Sanderson (STEVE MARTIN) is a constantly busy and thus divorced tax attorney who's met a woman in a law chat room. While preparing for their first meeting, he has to fend off a young upstart, Todd Gendler (MICHAEL ROSENBAUM), from landing a lucrative account with coffee heiress Mrs. Virginia Arness (JOAN PLOWRIGHT). Quick on his feet, Peter manages to do just that, although he's fully aware of the 74-year-old's staunch conservatism.
Peter's dexterity around dicey conditions is challenged, however, when his blind Internet date turns out to be a convict, Charlene Morton (QUEEN LATIFAH). Not only is he upset that she was charged and sentenced for armed robbery, but that this young, black urban woman is not the professional, middle-aged white one he believed. Meanwhile, she's upset that he's not the criminal lawyer as he led her to believe.
He wants her to leave immediately, but eventually puts her up for the night when she makes a scene that he worries might alert his racist neighbor, Mrs. Kline (BETTY WHITE), who just so happens to be the sister to one of his bosses at work. She then manages to infiltrate herself deeper into his life - including visiting him at work where his partner, Howie Rottman (EUGENE LEVY), is entranced by her - and refuses to leave until he agrees to help her and prove her innocence.
He reluctantly does so but must focus on getting Mrs. Arness to sign a contract with his firm. That results in Charlene having to put on various demeaning acts of servitude and deal with racist behavior from her and Peter's ex-sister-in-law, Ashley (MISSI PYLE).
At the same time, Charlene starts to enlighten him about her culture, as well as ways to reconnect with his kids, Sarah (KIMBERLY J. BROWN) and Georgey (ANGUS T. JONES), and ex-wife, Kate (JEAN SMART). As he does just that, he then sets out to help Charlene out of her legal mess, which eventually leads to his contact with her former boyfriend and current thug, Widow (STEVE HARRIS).