Cuffing season—the tendency for individuals to seek romantic partnerships during colder months—has been trivialized as a cultural quirk. However, for survivors of toxic relationships, this period represents a heightened risk of re-engagement with manipulative partners, particularly those with Cluster B personality traits (narcissistic, borderline, histrionic, and antisocial). This paper explores the neurobiological and psychological vulnerabilities that emerge during cuffing season, outlines the predatory behaviors characteristic of Cluster B individuals, and analyzes why no-contact boundaries are essential for preventing cognitive, emotional, and neurobiological harm. By synthesizing findings from neuroscience and psychopathology, the paper reframes cuffing season as a psychologically hazardous cycle rather than a harmless social phenomenon.