This research was conducted by combining the theoretical insights of communication accommodation theory and the communicative predicament model (CPM) of aging with methodological procedures drawn from the study of interethnic communication. Accordingly, young adult respondents were asked to describe two recent conversations with an older person, one satisfying and the other dissatisfying. Results indicated that older communicators in dissatisfying conversations were characterized as being underaccommodative and negatively expressive and as stereotyping young people. In response, young people frequently characterized themselves as reluctant accommodators. In addition, dissatisfying conversations were judged as more “intergroup” than those that were satisfying. Suggested improvements for dissatisfying conversations often were placed primarily on the shoulders of the older counterparts. In contrast, in satisfying conversations, older interactants were construed as supportive, telling interesting stories, astereotypical of older people, and positively expressive. However, these same encounters often were characterized by mixed positive and negative emotions, and few suggested improvements were proffered. The data are interpreted theoretically in relation to accommodation theory and the CPM as suggesting that both satisfying and dissatisfying intergenerational conversations sustain ageist ideologies.