Alisher Navoi’s version of Layli and Majnun (1484) is a significant Old Turkic epic poem that treats themes similar to those in William Shakespeare’s Romeo and Juliet (1597). As Navoi’s work has rarely been investigated in relation to Shakespeare’s play, this paper compares the socio-cultural and religious elements presented in these classic star-crossed love stories. Although the two authors lived in different times and regions and were influenced by different religions and cultures, they both showed interest in writing about the challenges facing tragic loves of their young protagonists. This study discusses the connection between the two poets’ lives and explores the ways in which their cultural and religious backgrounds, along with the written methods and forms of Islamic and European poetry, affected their treatment of this adolescent love story. It is argued that, despite the cultural, linguistic, and religious distances existing between the two worlds, the precarious position of women in both societies is nearly identical. Within the families of both societies, male and female children were treated differently, revealing a dominant gender inequality. Women had little freedom of choice or voice; the attitude of the male-dominated, patriarchal world towards women, whose lives were dictated by the men that ran the society, was similar in both traditions. The study also reveals the practice of the time, such as the upper-class families using forced marriage to retain their power. Furthermore, it demonstrates how profoundly religion influenced the progression of events in the works, as well as the words and deeds of the protagonists.