The East-West issue is one of the main subjects of Turkish literature in the modernization process. The novels which put this issue at the center often make a comparison in favor of the latter by putting the characters affected by the Westernization process in the Ottoman society against the characters that were not Westernized, in other words, that could remain original. In all his novels, although the intensity has changed, it is seen that Abdülhak Şinasi Hisar, who touched on the East-West issue, has a different attitude at this point. Leaving aside the character figuration of the authors of the Reform Era and Republican authors as opposing categories of East and West, Hisar tries to reach an East-West synthesis through three characters in his three novels called Fahim Bey and Biz, Çamlıca’daki Eniştemiz and Ali Nizamî Beyin Alafrangalığı and Şeyhliği. In this article, novel characters named Fahim Bey, Hacı Vâmık Bey and Ali Nizamî Bey, whose mission is to represent the three civilizations of Hisar, who focuses on the insanity of his characters which manifest as ‘halfness’, their incomprehensible aspects, social relations and conflicts with each other so as to reach a synthesis of civilization through these themes are examined in the context of East-West issue.