In this chapter, we investigate how individuals with chronic illnesses strategise to address their loneliness and how the social and cultural scripts available to them, such as individual responsibility, shape and influence these strategies. We uncover various approaches, including inward facing strategies such as maintaining a positive mindset and employing distraction techniques, as well as outward-facing strategies like reaching out and initiating connections. We also reveal obstacles to connection, such as fears of being a burden to others and societal expectations of self-reliance and independence. Tackling loneliness requires effort, emotional work, and the courage to face potential rejection, adding to the already substantial burden of managing chronic illnesses.