This article aims to address the practical question of whether there is educational value to embedding second-language (L2) learning experiences in intergenerational contexts. In particular, a case study was conducted of a novel, university-based ESL program in Hong Kong in which a group of older adult volunteers with a high level of English language proficiency skills engaged a group of college students with beginner to mid-level English language skills for an intensive three-month period of English language instruction, language practice, and intergenerational relationship building activities. The intergenerational context was reflected in the curricular activities designed to stimulate intergenerational (teacher-learner) sharing of real-life interests, stories, experiences, and perspectives. According to data from open-ended questions and IELTS-based English proficiency tests, the college students exhibited improved ESL skills and enhanced motivation to practice and extend their learning, while the older adult volunteers earned a valued teaching credential, improved their teaching abilities, and gained confidence and motivation for expanding their social linkages in the community. Implications for framing intergenerational encounters in ways that enhance meaningful ESL learning in real world contexts are considered.