Kelly O'Brien was the very living definition of the "spoiled rich kid." As the only son in his wealthy family, he took it for granted that he would simply be handed the job of running their company when his mother retired. The problem is that he didn't put in any work to make that happen nor did he intend to. That was simply unacceptable to his mother and sister. Kelly would have to be taught a lesson.
The company, O'Brien Secretarial, supplied "Girl Fridays" to overworked business executives worldwide and that gave the two women a brilliant idea. Kelly would simply have to become a Girl Friday himself to see what the job and company were really about. Against his protestations, Kelly was transformed into the very image of a young working woman. Unfortunately for him, his smooth complexion and soft features meant that the fake girl he was becoming was very attractive.