Many couples who come for therapy are struggling with separating from unconscious phantasies and beliefs that enmesh each partner with the other, resulting in states that popular songs powerfully epitomise. While this borderline experience is common and functional in the early stages of being in love its persistence paralyses the development of the relationship. Facing separation from and loss of illusion is a challenge couple therapists are often asked to help with. The argument is illustrated by a case, and by references to some of Cole Porter's best known songs.