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Cheating, as a psychological mechanism, is common to all, weaving through early family dynamics and evolving sexual identities. When it erupts in our love relationships, confusion, destruction, and de-integration of existing psychological states occur for all those affected by the cheating. The eruption of cheating can be viewed as a spontaneous response of the individual to disrupt a state of psychological stagnation and regression that may have no conscious path for dissolution. The transgressive actions bring up the possibility of a secret or separated consciousness, potentially breaking into states of existing merger in the established relationship system. This prior state of adaptation may have provided stability and security, while limiting the development of a separated consciousness with its urge toward acknowledgement. These essential, spontaneous elements in cheating can be found in Jung's later description of the psychology of the transference, where illicit impulses are seen at the foundation of the drive for individuation. The familiar psychological complex of the one betrayed is also explored, highlighting the potential for maturation in the one most wounded by the cheating. Clinical material is utilized here to amplify the relationship between cheating and the need for psychological evolution.