This paper has an aim at analyzing the aspects of aestheticism and calculated intention in Henry James’s Washington Square. Sloper, Morris, and Mrs. Penniman, the three major characters around Catherine have a tendency to manipulate and control other people, especially Catherine, with calculated intentions to get them or her to their own advantage. Sloper and Morris compete with each other in order to control or take possession of Catherine just like a property, and Mrs. Penniman tries to meddle with the love affairs of Catherine and Morris with her own melodramatic imagination. All the intentional activities of the three persons are closely combined with their aesthetic tendencies. Being ‘natural’ and ‘sincere’ is suggested as Morris’s motto but proves to be just his pose as an aesthete. The genuine meanings of the words ‘natural’ and ‘sincere’ belong only to Catherine in Washington Square. Her sincere efforts to love both her father and Morris and to determine her fate with her own will are the genuine criticism of the above three persons, and here lies the real nature of Henry James’s social criticism of American society in Washington Square.