This autoethnography traces the author's shifting masculine identities as they have evolved across time and contexts. This piece splices journals and blogs from the author's past with prevailing masculinities theory, spectral data (Nordstrom, 2013), post-structural feminist theory and the author's present gender identity to investigate what can be learned about gender flexibility within one person's lived experience. The paper offers a special glimpse into the masculine narratives the author performed during one phase of his early adulthood and opens possibilities for alternative discourses. By closely analyzing his gender expressions and identity, the autoethnography reveals moments when his masculinities intersect with and diverge from dominant narratives in masculinities, which fractures notions of a monolithic masculine experience. Ultimately, it suggests fractured masculinities that destabilizes gender and suggests masculinity is an always ongoing, incomplete, flexible, process of becoming.