This study examines intergenerational communication with a focus on the interactional patterns between Taiwanese younger and older adults at their first encounters. Two particular topics were focused on, namely, interruptions and painful-self disclosure, using frequency analysis to explore the extent to which older adults interrupt younger adults, painful-self-disclosure raised by older adults as well as the response types from the younger interlocutors based on the conversational data derived from 15 pairs of Taiwanese younger and older adults’ first-encounter talks. It is found that older people interrupted their younger interlocutors to a greater extent and when older adults engaged in painful self-disclosure, their younger interlocutors more likely demonstrated an attitude to alienate themselves from the raised painful topics, for instance, by repressing the topics, changing to more positive topics or simply giving minimal responses. The results are discussed in relation to whether there could be clues in this study to explain why intergenerational communication could be unsatisfying and how power from age difference could be observed.