Winnicott's concept of transitional relatedness has captured the interest of psychoanalysts because it provides an understanding of the dialectical process occurring between inner and outer reality, and by extension, between analyst and analysand. Clinical observations related to transitional phenomena have led the authors to develop a projective early memory probe that assesses transitional phenomena. The transitional object early memory probe was tested both for its empirical validity and for its clinical utility in psychodynamic psychotherapy. Construct validity was assessed by comparing memory scores to the Rorschach Transitional Object Scale, as well as to therapist ratings of patient behaviors. Results demonstrated moderate correlations between early memory scores and Rorschach scale scores. Equally important was the finding that early memory scores were significantly correlated with therapist ratings of key behavioral patterns in therapy. A case vignette highlights the clinical application of the transitional object probe in assessing the capacity for transitional relatedness. In this case, the data gleaned from the patient's memories provided the therapist with a sharper focus on their role in the patient's growing capacity for more vital and creative contact with reality.