As profoundly self-conscious and reflective men, Axel Heyst in Joseph Conrad’s Victory and C. in Yusuf Atılgan’s Idle Man are immobilized and incapacitated by their excessive reflective faculty and suffer from disappointment in their romantic relationships due to their avoidant attachment styles. Lacking a caring mother figure who could provide them with loving compassion, they are brought up by emotionally unavailable fathers who are clearly not attuned to the needs of their sons. So while growing up their attachment needs are clearly not met by their primary caregiver who neglects and occasionally abuses them instead. Growing up to become “avoidant” adults, they experience problems with intimacy, invest little in social and romantic relationships and are unable or unwilling to share thoughts and feelings with others. In what follows, I will examine comparatively the psychological dynamics underlying Heyst’s and C.’s avoidant attachment styles and explore how their gender performances are fraught with anxieties and insecurities. Ultimately, I argue that the traumatic deprivations of Heyst’s and C.’ childhoods significantly hamper their ability to form strong and lasting emotional bonds, making it impossible for them to find satisfaction in romantic relationships.