In an object relations study on infidelity and obsessive love, the author observes that in relationships marked by chronic, repetitive infidelity and obsession, the lover is enamored with that which they can not have and that the psychological development of such individuals may have been traumatized by early attachment disturbances in the primary dyad. Tenacious, unsatisfying love-attachments as seen in sexual addictions and obsessional love may result from the internalization of an absent or intermittent object relationship—a morbid attachment to the “missing” object of infancy. Such patients often demonstrate depressive/addictive traits and schizoid defenses and typically have difficulty forming an attachment bond with the analyst, perceiving the analyst as a dangerous, rejecting agent who will recapitulate the original trauma. In the clinical case of Gretchen, the author uses Winnicott's (1960) concept of “holding” to create a progressive therapeutic bond, as toxic resistant forces are gradually resolved.