As the number of seniors with memory loss continues to rise, the importance of designing tools that facilitate connection with loved ones to reduce feelings of isolation is becoming increasingly apparent. Feelings of isolation have been linked to poor health outcomes and consequently place larger demands on health care systems, health care professionals, family members, and friends. Seniors with memory loss (SWML) have a higher risk of becoming social isolated, and isolation can accelerate the rate of memory loss. This research addresses social isolation among this population by exploring ways to engage them in co-designing solutions. Traditional research methods and communication technologies may not be appropriate or may need to be modified in order to engage SWML. Through a combination of participatory design, co-design, and generative tools, this research explored: (1) current research methods and techniques used to engage SWML in the design process, (2) the evaluation of existing and new design techniques through the facilitation of three pilot studies, (3) and insights and recommendations to engage this population in future work.