Weng Chia-yi was a classmate of Chiang Ching-kuo's eldest daughter, Hsiao-chang, at Tamsui Girls'  School. The two girls were of similar ages and often studied and played together. Photos of Weng Chia-yi attending birthday parties and family gatherings at Hsiao-chang's home reveal the close friendship between the two. Because Weng Chia-yi frequently visited the Chiang family, she became well acquainted with Hsiao-chang's parents and her brothers Hsiao-wen, Hsiao-wu, and Hsiao-yung.

Among the donated artifacts, in addition to many photos of the two close friends from their youth, there is also a photo of Hsiao-wen in military uniform that he gave to Weng Chia-yi as a keepsake. Hsiao-chang also gave Weng Chia-yi a photo of herself, which had a special message reminding them not to forget each other. Chiang Ching-kuo was very fond of Weng Chia-yi. On the eve of her marriage and departure to the United States, he specially inscribed the words “the fabled roc flies ten thousand miles” on an ink painting personally drawn by Hsiao-chang to wish her all the best for the future, and also gifted her a copy of the book My Father.