The history of the term confrontation is reviewed. It is suggested that the reason it was so difficult to define the term over the years is that it is fundamentally an interactive term, imported into an era in which many analysts behaved as if there were no interaction—or should be none. Contemporary analytic process can be seen as a series of confrontations between two people by virtue of the intrinsic differences between them. Three clinical vignettes illustrate this point and its implications. A final section of the article examines the dialogue between the Fool and King Lear in Shakespeare’s (1606) play, which allows consideration of the complex nature of confrontation and other aspects of therapeutic dialogue often neglected.