This chapter explores how a subset of Caribbean men—specifically Jamaican and Trinbagonian males—navigate and reflect on their identities, masculinities, and sexualities during their university years. Using an autoethnographic and narrative inquiry approach, I interweave my reflections with in-depth interviews of seven Caribbean men to examine the interplay between perceived “natural” male traits and the social expectations of manhood. The concept of critical masculinity is central, providing a framework for men to critically assess which traditional masculine norms to embrace or reject as they strive for personal growth. Findings reveal that while hegemonic ideals such as athletic prowess, heterosexual dominance, and emotional restraint strongly influence these men’s lives, there are also clear signs of change and contradiction. The men experience tension between innate emotions and societal pressures, highlighting how the natural and social aspects of masculinity can sometimes conflict. By fostering a safe, reflective space for storytelling, this work illustrates that embracing vulnerability, and critical self-examination can enable more inclusive expressions of masculinity. Ultimately, this chapter offers nuanced insight into Caribbean masculine identity and underscores the importance of critical reflection in expanding what it means to “be a man.”