The revolution in communication technology has resulted in more age-segregated conversation among adolescents. In a similar way, older adults have increased online conversations with their peers. This article explores some obstacles that prevent the intergenerational connections needed for mutual understanding and care. Several research emphases are described that together define the complexity of intergenerational dialogue. The concerns provided for consideration include (a) age-segregated communication practices of adolescents and older adults, (b) willingness of older people to disclose personal opinions and feelings to younger people, (c) need for general adoption of the reciprocal learning concept to support harmony, (d) amount of time spent with adolescents as a predictor of parent and grandparent success, (e) learning expectations for later life that contribute to productive aging, and (f) recognition of the leadership role that adolescents should assume to reconnect the generations. Attitude and behavior change are recommended for older adults, adolescents, parents, educators, and school stakeholders.