After establishing herself as a bankable star with the fish out of water comedy Legally Blonde, Reese Witherspoon returns in what could be described as a "fish back in water" comedy. Melanie Carmichael (Witherspoon) is a successful New York fashion designer who is dating Andrew Hennings (Patrick Dempsey), a wealthy socialite whose mother, Katherine Hennings (Candice Bergen), is the Big Apple's mayor. One day, Andrew pops the big question and asks Melanie to marry him; Melanie is overjoyed, but unknown to Andrew, Melanie has some unfinished business to take care of first. Despite her polished uptown image, Melanie grew up poor in the deep South, and as a teenager she married her high school sweetheart Jake Perry (Josh Lucas). Things went sour and Melanie moved East, reinventing herself along the way, but Jake never bothered to legally end their marriage. Now Melanie has to return to her hometown of Pigeon Creek, AL, to tell her parents (Fred Ward and Mary Kay Place) the news and convince Jake to grant her a divorce; however, the more time she spends with her old flame, the more she feels sparks flying between them again, while she also learns her Eastern affectations don't fly with everyone back home.