In this article, we reflect on the role of heartache during the first 2 years of The LGBTQ+ Intergenerational Dialogue Project. The project--a partnership between an LGBTQ+ community center, an art and design college, and a public research university--brings together racially, socioeconomically, and gender diverse cohorts of LGBTQ+ young (18-26 years old) and older adults (62-81) for dialogue, creative collaboration, and shared dinners. The project was conceived as a collaborative ethnographic pedagogical experiment in which participants became partners in research, education, and community formation. We quickly realized that heartache would be central to our journey together, as we navigated this rare opportunity for LGBTQ+ intergenerational contact. Grief, anger, and pain generated through interactions between LGBTQ+ people can be surprising, and especially weighty, components of Queer Battle Fatigue. It is necessary, we argue, to explore the heartache we experience within queer spaces as a pedagogical tool with which to strengthen queer communities.