Because the process of judging something difficult is subjective, this chapter does not illustrate difficult case material but rather invites us all to ask, What makes a case difficult? We can answer this question by unblending and listening when and if our parts react to a couple’s issues and dynamics in therapy. These issues may strike us as common or unusual, explosive or poignant. They include the couple’s relationships with extended family members, parenting philosophies, money, sex, extramarital affairs, violence, separation, divorce, illness and more – all topics of potential significance to anyone, including any therapist.