Chosŏn Korean intellectual Kim Chŏng-hŭi visited Yanjing (Beijing’s ancient name) with his father on a diplomatic mission at the age of 24. Through discussions with scholars of the Qianlong-Jiaqing Scholarship, Kim began his lifelong research on, and involvement with, the academic trends of the Qing dynasty of China. Kim visited Weng Fang-gang because of his interest in calligraphy and Chinese painting, gaining an appreciation of Weng’s rich collection. This study focuses on the connection between Weng and Kim that stemmed from the gifts of portraits, investigating the anecdotes and related issues of Kim and his friendship with intellectuals in Yanjing from the perspective of receiving presents. Portrait-based texts have been an indicative element of the East Asian Sinosphere in the last few centuries. On the basis of long-term research on the portrait culture in the Ming and Qing dynasties of China, the author of this study examines the evolution of Chosŏn’s art and literature perspectives. Portrait giving as presents between intellectuals is adopted as a concrete clue, regarding which the similarities and differences between the ideas and aesthetic tastes of intellectuals in the two countries are explored, an overview of the history of portraits in the middle and late periods of Chosŏn and the major transformations are presented, and the correspondences between the portrait culture of the two countries are identified. Kim witnessed numerous portraits used as presents in the intellectual circle of Yanjing. Therefore, these presents not only facilitated forming transnational connections between intellectuals, but also served as an excellent perspective for contemporary scholars to investigate the cultural effect of the interactions and mutual influences occurring in the East Asian Sinosphere.