Memory loss and dementia can be devastating for both caregivers and care recipients. Narrative therapeutic approaches offer promise, as well as challenges, for social interventions with couples where one partner has dementia. The Couples Life Story Approach is a recently-developed method by which practitioners work with such couples to help them narrate the story of their life together. This narrative approach is augmented by mementoes (e.g., photos, cards) that are collected by the couple during the intervention. Significant memories are elicited from both partners and developed into a Life Story Book. Drawing on data from this clinical research intervention with 20 older couples, we ask: What are some of the challenges of conducting narrative-based therapeutic interventions with older couples with memory loss? Clinical themes were identified utilizing a multiple case study approach during weekly team meetings. Six of the most prominent themes are presented here. Specifically, how to: (1) construct a narrative from disparate stories, (2) tell a mutual story, (3) tell the story of a couple that has been in a shorter relationship, (4) incorporate others in the story, (5) include difficult life moments, and, (6) end the story. Within each theme, we utilize case examples to illuminate relevant issues and describe strategies that were developed to resolve these clinical challenges. Implications for practitioners and clinical researchers who are engaged in dyadic interventions are discussed.