This paper will look into problematical representation of male characters in Nam?k Kemal’s novels and Nuri Bilge Ceylan’s films with a focus on interpersonal relationships of male protagonists with female characters. It explores how a certain male character type, the orphan, that emerged in the Tanzimat (reorganization) era novel, particularly in Nam?k Kemal’s novels, as a result of the social, intellectual, and political milieu is transformed into a problematic, “distant” 21st century modern man in Ceylan’s movies. In the novels of Tanzimat era that center on the orphan character, novelists had created two female characters that are portrayed as complete opposites to educate fatherless sons. In this plot, the orphan struggles between the ideal woman who is the embodiment of traditional values and the femme fatale who is the symbol of degeneration and foreign life style. Although the protagonist’s choice between the two female characters was intended to symbolize a young Ottoman’s struggle between East and West, a close reading reveals a narcissistic tendency shared by both male writers and male characters. On the other hand, Ceylan, in “Distant” (2002) and “Climates” (2006), takes on the similar web of relations and character formation and adapts it to bring meticulous insight into crisis of urban masculinity. His use of different female characters in his films serves to bring out egotism of alienated male characters, rather than to “educate” them. Different approaches to the same narrative by novelist Namik Kemal and director Ceylan brings to light the transformation of the male perspective on masculinity from Tanzimat to today.