This chapter takes an interdisciplinary approach to studying the representation of aging and intergenerational relationships in Hallmark films, drawing on aging studies, critical gerontology, gender studies, and television studies. It investigates how Hallmark presents older characters and their connections with younger generations, with a special emphasis on alterations in depiction after 2020. Previously restricted to supporting parts, older characters are now more prominently featured, tackling issues such as Alzheimer’s and the difficulties of new living arrangements. This chapter investigates how these films represent changing societal attitudes toward aging and intergenerational relationships. The study found that Hallmark films have a more balanced representation of age and gender than Hollywood’s top blockbusters. Despite a lesser presence of actresses aged 60 and up, Hallmark has higher visibility for older actresses than Hollywood, which corresponds closely to population trends. The representation of older characters is divided into three basic archetypes: The Bitter, The Cheerful, and The Wise. These roles, while frequently clichéd, provide a lens through which traditional values are both perpetuated and challenged in the context of current life. The chapter emphasizes that, while Hallmark films have made gains in incorporating elderly characters into core stories, these representations are still idealized and lack diversity. Elderly people continue to function as traditional value anchors, showing an ongoing challenge to depict aging in a way that is realistic while also fitting into the genre’s idealized environment.