How does the essay documentary curate truth, and who benefits from the personal transparency required of the essay film – the audience or the filmmaker? This research creation examines the thematic and conceptual research and created methodologies employed by Montreal filmmaker Adrian Wills to create his first essay film “Baby Boy Cousins”. Adopted as an infant, Wills embarked on a two-year journey in search of his birth family in Newfoundland for this research creation. Through real-time documentation, he uncovered the heartbreaking truth that his birth mother had taken her own life, amongst other family secrets. “Baby Boy Cousins: Looking for Roots, the Essay Documentary” investigates the essay film’s unique ability to authentically explore subjective experiences and emotions while acknowledging the limitations of objective truth. It explores the work of acclaimed essay filmmakers Sarah Polley, Alan Berliner, Chantal Akerman, and Deann Borshay Liem in relation to the construction of “Baby Boy Cousins”. Moreover, this research creation examines the intricate ethical considerations surrounding personal transparency. It investigates the delicate balance between meeting audience expectations and safeguarding the privacy of the filmmaker. “Baby Boy Cousins: Looking for Roots, the Essay Documentary” concludes with profound insights into the transformative power of personal filmmaking while acknowledging the essay filmmaker’s need for psychological self-care when engaging in personal vulnerability.