John Lyly’s Endymion is recognized for its portrayal of the Neoplatonic ideals of love and beauty, with Cynthia, the moon goddess and earthly queen, celebrated in a Petrarchan convention. Amidst the exploration of love versus friendship and lust versus contemplative affection, characters comprehend human mortality and the ironic value of constant inconstancy Cynthia represents. While the play is often viewed as a political allegory of Elizabeth I and her court, this paper shifts focus to the gendered discourses of love and friendship. Women are depicted as hypocritical, lustful, and morally unstable. Endymion conceals his love for Tellus while desiring Cynthia; Cynthia harshly judges Tellus and Semele, reflecting patriarchal gender norms. Eumenides, epitomizing true love, prioritizes male friendship over love, perpetuating a gender-biased view that positions friendship and love as conflicting values. Consequently, Lyly’s exploration of true love is hindered by misogynistic ideals inherent in masculine discourses of love and friendship.