In this digital era, online intercultural exchange has gained increased popularity in language and culture education. However, concerns arise over its productiveness and efficacy in engaging participants cognitively. In addition, there is a paucity of research on out-of-classroom synchronous online exchange projects, let alone those involving Chinese English learners and English-speaking Chinese learners. Guided by the social constructivist theory, this study examined the productiveness of a small-scale intercultural online exchange project from its quality dimension measured by the participants’ use of questions. The purpose was to gain a better understanding of the dynamics and educational value of online synchronous text communication in language and culture learning. Participants were six English learners from China and six English-speaking Chinese learners from the U.S. Unlike many previous intercultural exchanges, this project was entirely independent from the curricula on both sides. Within a certain time frame, participants chose when and where exactly the synchronous text chat took place. Data analyses focused on the self-generated questions found in chat logs. Although participants seemed to self-generate more lower-order than higher-order thinking questions, the latter were frequently used in the process of online discussion to engage learners from both sides in critical thinking and self-reflection. Differences in the use of questions were found across dyads, languages, and groups of participants. Implications for future research and project design were discussed.