This study adopted various methods such as qualitative research, observation, interviews, and document collection to examine the emotional responses, behavior changes, and counseling effects on a single-parent child in a skipped-generation family before or after a series of painting activities. The participant was asked to take part in 50-minute sessions twice a week for 8 weeks (16 unit activities in total). According our research findings, after the painting activities: (1) The subject in this study exhibited significant improvement in personal relationships, and there was a positive performance in social interaction, namely, more initiative and willingness to share with others; (2) The subject became more active in his family activities, and he tended to have more positive interactions with his grandmother; (3) The subject created significant positive changes in terms of inherent abilities, learning motivation, self-affirmation, and self development; and (4) The subject had significant improvement in learning performance in kindergarten; and (5) The subject's communication and expression skills were dramatically enhanced. During the painting projects, the subject did maintain good interactions with researchers and was very pleased to share more through self-disclosure. Hence, this study will provide conclusions and suggestions in accordance with these research findings, which can serve as a valuable reference for future research as well as for any pre-kindergarten teacher who is counseling children living in skipped-generation families who are more likely to have poor social interactions. (Contains 2 tables and 2 figures.)