All's Well That Ends Well, a play produced when Shakespeare emerged as London's leading playwright in the mid-1590s, seems to be nobody's favorite: it was not popular with its first audience, it is rarely acted, and it has seldom received much praise from critics. The play is about an abandoned wife who accomplishes a series of seemingly impossible tasks in order to regain her prodigal husband. Though originally classified as a comedy, the play is now considered one of Shakespeare's problem plays, so codified because they cannot be neatly classified as either tragedy or comedy. The title of this play is the proverb ＂all's well that ends well,＂ which means the process does not really matter as long as the outcome is good. The ending of the play, however, has been a focus of critical discontent and has bothered its audience/readers for four centuries. Is this disturbing ending an intended effect or simply a failed attempt of the Bard? I will answer this question in the following paper. Drawing on the theories of psychoanalysis, particularly the object-relations of Melanie Klein (1882-1960), this essay aims to map out that space where a late adolescent is wrestling his way to adulthood and thereby spell out his resistance to marrying the heroine. I propose that this is a key to understanding the play and to explaining its lukewarm reception. The main problem of this play, I shall argue, rests on the hero's mental pain or growing pain of not living in an ideal world. His final recognition that love itself is not simply a phantasy but a matter of complex adjustments marks the beginning of his real, adult journey. To read All's Well as a rich inner phantasy life of Bertram, I shall look at the psychological processes of the hero and how they are put into the context of crucial experiences of his story and relationships