Pollyanna syndrome, the name being taken from a book of the same title, means “an excessively or blindly optimistic person.” The occurrence and danger of such attitudes in psychotherapy is discussed. Such attitudes may occur both in patients and their therapists. Either of them may say “things will not be so bad...” attempting to console not him/himself but the other party. The main aim of psychotherapy is to facilitate taking responsibility and decisions. But there are also other aims, identical to those attributed to philosophy in ancient times, namely, “to treat the soul” or, clinically speaking, to provide consolation. This is usually achieved by attributing meaning and purpose to suffering and set-backs. In the paper, I discuss how the therapist could avoid the trap of being and coercing the patient to be “optimistic, positive, and strong” when the situation does not necessarily warrant such an attitude. Philosophy may be of help here. One may apply theodicy, that is, the philosophical attempt to explain and justify the evil existing in God's world. Another possibility is Ericksonian approach of utilization, paradoxical intervention, using metaphors and hypnotic techniques in order to let the patient come up with his own, intimate resources facilitating recovery. Logotherapy, which is an existential approach is recommended, either as such or as a part of REBT. In short, the difference between an ineffective and an effective approach is the difference between being optimistic and being realistic.