All's Well That Ends Well has been classified among Shakespeare's "problem plays," due to its ethically uncomfortable premise and an ending that resists clean resolution. Central to this discomfort is Helena, a character who has divided critics and audiences for centuries — read alternately as an admirably persistent heroine and as a deeply troubling figure. This paper argues that the latter reading is more psychologically accurate. Through the application of Tennov's (1979) theory of limerence and Bandura's (1978, 1986) framework of reciprocal determinism, Helena's pursuit of Bertram is examined not as romantic persistence but as a clinically recognisable pattern of obsessive attachment, sustained and escalated by a socially enabling environment. Textual analysis reveals the presence of core limerence markers — intrusive cognition, non-substitutability of the limerent object, idealization, and behavioural escalation under rejection — across key scenes of the play. Further, the triadic interaction of person, behaviour, and environment demonstrates that Helena's limerence does not self-correct precisely because her social world is structured to prevent it from doing so. The paper concludes that the play inadvertently stages the conditions under which limerence becomes chronic, with implications for understanding rejection-triggered aggression and the psychology of obsessive pursuit.