While scholars have often acknowledged the relationship between Bernstein and Blitzstein by focusing on their Jewish immigrant backgrounds, shared love for the musical theatre, modernist approach to music, and socio-political goals, there is little discussion on how their sexual orientation might have shaped this friendship and their work. Yet, attempting to understand the bond between the two composers, both married yet unequivocally gay, without considering their queer identities leaves a major component out of the picture. In this chapter, I consider the queer intimacies that are at the core of their bond and how works that they dedicated to each other – Bernstein’s Trouble in Tahiti, an opera about gender alienation; and Blitzstein’s Six Elizabethan Songs, a set of pieces concealing possible homoerotic meanings – can uncover new perspectives on their friendship and compositional approaches.