Outside of Western contexts, natural-conversation-based research on intergenerational communication is relatively rare. To help redress this imbalance, this paper explores the conversational styles of first-encounter talks between five pairs of college students and older adults in Taiwan, and infers the interactional norms that underlie them. It is found that younger Taiwanese adults tend to exhibit great formality in their conversational styles, manifested as frequent appeals to older people’s positive face, and a preference for quick question-asking especially at the opening of the talks. Older adults, in contrast, exhibited lower levels of commitment to eliciting information from their interlocutors and were more likely to interrupt them. Younger adults appeared uneasy when hearing older adults’ painful self-disclosures, as reflected in the former’s minimal responses or quick shifts to other topics. The conversational styles pinpointed by this research are discussed in terms of how the observed intergenerational communication could be problematic.