Due to a constant increase in the proportion of older people in the world, the problems of their integration into society, the motivation for a positive change in the quality of life, the expansion of the communicative space, and bridging the digital divide are becoming more prominent. One way to solve such problems is intergenerational interaction. When it is organized, the general interests of older and young people are emphasized, and conditions are created for the mutual exchange of experience and acquisition of new skills. For this purpose, special educational projects and programs have been developed. However, their implementation can be successful only when considering the readiness of representatives of both generations to productive interaction. This conclusion was made on the basis of the results of the pilot survey of older people (n = 68, aged from 58 to 91 years) and adolescents (n = 163, aged from 11 to 15 years). Taking into account the obtained data, programs of psychological and pedagogical support have been developed for different age groups, including workshops. The article presents one of them - a workshop for older people let’s talk heart to heart.