This paper explores the precariousness of hegemonic masculinity in Rashid Al-Daif's writings, particularly focusing on the impacts of shifting gender roles, aging, and globalization on the construction (and deconstruction) of masculine identity. Engaging with masculinity studies and feminist theory, I offer a close reading of texts including Ṭiṣtifil Meryl Streep (Who’s Afraid of Meryl Streep?), OK, maʿ Al-salāmeh (OK,Goodbye) and What Makes a Man?, highlighting the contradictions of masculinity, as experienced by al-Daif male narrators. As al-Daif’s male protagonists face an increasingly globalized, or rather “glocalized” reality in contemporary Lebanon, they experience deep anxiety about not only their own status in the world, but also the state of their Arab culture and nation. Even seemingly trivial issues such as the widespread proliferation of the English language and cable television become sources of anxiety, as the former renders them incompetent (even impotent), while the latter threatens to “corrupt” their women folk because of its propagation of seemingly loose moral standards and blurred gender roles. At times, the narrators seem to disavow some of their reified notions of “manhood” and “womanhood.” Other times, they go to great lengths to assert an essentialized masculine identity that rejects alternative, and more fluid, performances of masculinity (and femininity). Often times, they inevitably crack down as they find themselves in a crisis, where neither their complicity with nor their rebellion against normative values and practices seem to enhance their intimate relationships with the women they love (and resent). I argue that while al-Daif’s narrators may display aggressive masculinity, or machismo, the texts often expose these protagonists’ underlying vulnerabilities and the unfortunate predicaments resulting from the narrators’ conscious or unconscious reinforcement of dominant masculine ideals. By revealing the “the cracks and fissures that belie the complications and contradictions embedded in the masculine project” (Whitehead and Barret 2001: 19), and by demonstrating the “cost” of complicit masculinity in the life of the novels’ tormented male narrators, the texts elucidate the precariousness of performing dominant masculinity, let along clinging to an essentialized male identity. In the face of shifting material realities such as women’s increased participation in the public space, late capitalism, evolving gender roles, and personal life changes such ageing and illness, al-Daif’s male protagonists ponder and learn, sometimes the hard way, that there are no easy answers to the increasingly elusive question “what makes a man?”.