In the contexts of population aging and English as a second language (ESL) proficiency decline in Hong Kong, a 12 weeks program that matched 15 retired citizens with 30 secondary school children who wanted to practice English outside the classroom was established. Using proficiency tests, open-ended questions, and Likert scales, this study examined the program value in terms of participants’ program experiences and performances. Results indicated that intergenerational contacts through games, activities, mutual understanding, and friendships appeared to be conducive to children’s ESL learning and relevant to retirees’ post-retirement development. Ideas on exploring ways to increase more available linguistic practice encounters while promoting active aging, and an insight on responding to intergenerational segregation are considered. Copyright ©Routledge.