Fantasies whose core is constituted by the notions of "someday" and "if only" are ubiquitous in human psyche. In severe character pathology, however, these fantasies have a particularly tenacious, defensive, and ego-depleting quality. The "someday" fantasy idealizes the future and fosters optimism, and the "if only" fantasy idealizes the past and lays the groundwork for nostalgia. The two fantasies originate in the narcissistic disequilibrium consequent upon the early mother-child separation experiences, though the oedipal conflict also contributes to them. Both can be employed as defenses against defective self and object constancy as well as later narclssistic and oedipal traumas. This paper attempts to highlight the metapsychology and behavioral consequences of these fantasies as well as their unfolding in the treatment situation. It suggests six tasks to be especially important for analytic work with such patients: (1) providing and sustaining a meaningful "holding environment"; (2) employing "affirmative interventions"; (3) helping the patient unmask these fantasies and interpreting their defensive, narcissistic and sadomasochistic aspects; (4) rupturing the patient's excessive hope, analyzing the effects of such rupture, and facilitating the resultant mourning; (5) reconstructing the early scenarios underlying the need for excessive hope; and (6) paying careful attention to countertransference feelings throughout such work.