Difficult histories expose learners to historical suffering and victimization that constitute a collective trauma. The difficulty stems from the strong emotional reactions or ethical responses learners may evince, undermining their trust in security and morality of this world. However, difficult histories may also expose learners to instances in which their own nation, or the ethnic/social group to which they belong, played the role of perpetrator. Learning that their nation, and implicitly even their direct ancestors, victimized a minority, enslaved or behaved atrociously towards a group of people, oppressed and conquered other nations, may arouse in learners a sense of collective guilt. This perspective on difficult history draws from basic assumptions of social psychology. The difficulty here stems, not just from the unsettling emotion, but from the blow to the individual's self-esteem stemming from the negative image of the group. Such a history is difficult because it collides with learners' need to identify with their nation or ethnic group and to view it as inherently benevolent. This article examines how teaching difficult histories has many challenges but it also offers important opportunities.