In contemporary romantic storytelling—across literature, film, and serialized television—the "checked relationship" has emerged as a dominant trope. Defined as a romantic partnership subject to external auditing, internal scorekeeping, or conditional validation, this dynamic creates narrative tension by juxtaposing intimacy with accountability. This paper examines how checked relationships function narratively, psychologically, and culturally. It argues that while such storylines resonate with modern anxieties about trust and performance in love, they risk reifying transactional views of affection. Through analysis of canonical and recent examples, this paper explores how creators use checks (e.g., social media scrutiny, friend-group approval, contractual agreements, or “break-up clauses”) to generate drama, and how resolution often requires transcending the very framework of checking.