Whether stemming from dysfunctional families, abuse, emotional responses to societal violence, the threat of terrorism, school shootings, or escaping the day-to-day tedium that life places before us, today's learners are vulnerable to loss and the grief, sorrow, depression, and anger that accompany such loss. This essay, written from the lead author's perspective, draws on her classroom experience, presenting personal stories and student work. Both authors connect these examples to research and best practices by offering a theoretical framework for understanding the role of emotions in learning and providing educational strategies that simultaneously equip students to cope with painful emotions and empower them to embark upon higher-order thinking and learning.