Abstract: Introduction: The community outreach program Amigos do Sorriso (Friends of Smiling) is based on the understanding that community outreach programs are part of academic training because they provide experiences that result in exchanges between the students and the society. The participants are undergraduate students from the healthcare field, who develop ludic activities focusing on humanization, health education and the resulting multiplying effects. Since 2010, fortnightly activities have been conducted at an old people’s home with the aim of offering playful experiences involving creative and communicative strategies, in order to give new meaning to old age through playing. The objective of this article is to describe these experiences and understand what the medicine students have learned from them. Methods: this article presents a qualitative study, based on 13 narratives written between 2018 and 2019 by undergraduate medicine students who were involved in activities at the old people’s home. The content was analyzed from a thematic perspective and correlated to the theoretical framework. Results: Three thematic categories were identified: playing with the elderly, handcrafted construction of communication and sharing between generations about aging. The participants discussed the different forms of play, its relations with health promotion and the specific characteristics of developing Ludic activities with the elderly. Through play they were also able to explore various forms of communication: talking, listening, sharing stories, and respecting the moments of silence, that led to agreement and disagreement. Finally, they discussed the aging process, elderly heath, elderly people in care and the contact itself between generations, allowing the students to reflect on themselves. Conclusions: The activities in the old people’s home enabled the students to appreciate the potential that strategies of play offer in terms of promoting autonomy and health, without infantilizing the elderly. It allowed them to identify strategies to form closer relationships and ties with the elderly subjects, respecting individual and collective boundaries when sharing stories and feelings with empathy. Hence the highlight of the program was the development of skills, both general and specific for elderly care, among future medics, recognizing that the aging is a process that involves us all.