This chapter tests the limits of understanding what masculinity means or tries to mean. It insists that queer masculinities are those that are not only suspicious, resistant, or out of the ordinary, but are also those that elude while stabilizing meaning. In other words, at the moment we examine the Rocky Horror Picture Show or an online dating site, we establish a set of assumptions regarding who people are; yet, we develop this interplay of subjectivities that presumptively iterates binaries without ever challenging how heterosexuality is nothing more than a construction of the masculine ideal. The chapter beckons us to not get too comfortable with our learned sense that we know what masculinity is. It turns our assumptions regarding masculinity topsy-turvy and forces us to recognize that whether you are a Rasta, rude boy, martial artist, womanizer, athlete, or soldier, masculinities are defined social constructions that vary across culture, context, and community.