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Scholars writing about men who have sex with men (MSM) have theorized anal sex positions to dictate gendered sexual scripts of dominance and passivity that are often racialized. However, absent in this literature are qualitative accounts of how men who avoid anal sex navigate sexual experiences with other men. While most people assume gay men identify with either top, bottom, or versatile anal sex positions, most men who have sex with men surprisingly report not doing anal sex. Among new sexuality labels gaining traction is the term “side” - a sexual position and label describing men who do not engage in anal sex and thus identify outside of the top/bottom binary. In this paper, we draw on in-depth interviews with 20 participants and counting in Toronto over 18 years-old identifying as men and sides. We ask the following: How are sides negotiating sex and romantic relationships with other men? Learning from the experiences of sides poses opportunities to challenge assumptions of current understandings of MSM sexuality labels, behavior, and gender assumed to be focused on anal sex.