This dissertation is an auto/ethnographic account of close friendships between the researcher and other men. The various narratives contain intimate dialogues about being a man, having friends, and the process of resisting and succumbing to orthodox masculinity. The purpose of the research was to investigate and artfully depict the communication and development of close friendships between the researcher and other men, in hope of gaining more knowledge of the difficulty forming and maintaining male friendships given the strictures of orthodox masculinity. The research combines methods of autoethnography and dialogic conversations with four male friends. In the first chapter I set the stage with a review of the scholarly literature on male friendship and masculinity. In chapters two through six and nine through eleven I present two sets of dialogic conversations I had with four men. Chapter seven provides a theoretical tour of the method. Chapter eight consists of monologues about friendship given by three participants. Chapter twelve concludes the dissertation with personal reflection and analysis. The analysis draws links between the author's experiences of friendship with each participant, grounding research on masculinity, as well as research on male-male friendship. In male-male friendships, the performance of masculinity, especially proving one's manhood, reverses the order of expected dialogical tensions in interpersonal relationships. For example, to be a man requires demonstrating invulnerability before allowing vulnerability. Forming close personal bonds, however, requires demonstrating vulnerability from the onset, something that runs counter to prescripts of orthodox masculinity. This observation demonstrates the double bind many men face when first forming friendships. To counter this bind, I argue for the need of a reflexive turn at level of self to provide the necessary gap in self-knowledge that allows for dialogue and redefinition of orthodox masculinity between men.