Bears are a subculture predominantly composed of gay, bisexual, and queer men who valorize and eroticize fat, hirsute, and aging bodies that tend to be stigmatized in mainstream gay and straight communities. For many of the men, the Bear community is a safe space that allows them to grapple with social rules and norms as they pursue emotionally and physically fulfilling relationships. In this talk, I draw on experiences from my 10-year engagement with the Malaysian Bear community to examine how couples participating in the community were continuously trying to mediate the harrowing effects of societally induced body insecurity within their relationships. I discuss how my interlocutors navigated feelings of tension and insecurity that arose in situations when different body practices—namely eating and exercising—became the subject of disciplining efforts in their relationships, all in the name of love. In doing so I demonstrate the immense difficulty of being able to work outside the logics of competing discourses around fatness that tend to collapse and conflate ideas about the body, health, desirability, and moral responsibility—even among member of a subculture that does its very best to undo the harm these discourses can cause.