The author argues that psychoanalysis has a history of confounding social customs with developmental milestones and measures of normality. Using the idea of life-long coupled relationships being commensurate with psychological health as an example of the sort of social custom that is still embedded in our clinical theories, this paper seeks to illustrate how such biases continue to negatively impact clinical treatment and disrupt theoretical advances. Writings in neo-Kleinian psychoanalysis, relational psychoanlysis, self psychology, and attachment theory are discussed and critiqued. It is argued that our theories can, with some patients, mislead us into reaching for the wrong developmental milestones, potentially collude with the patient's own fears, and exacerbate feelings of dread and neglect underlying hopeful, healthy, and creative developmental strivings that are present. Intersubjectivity is suggested as a clinically and theoretically flexible approach that may avoid these pitfalls.