The purpose of this study was to verify the possibility of setting multi-boundaries and to reconsider the meaning of intergenerational learning. The focus was on a school-community partnership organization called S Junior High School Support (S-Sapo). The data for the study are from fieldwork conducted in the organization from April 2016 to June 2020. The analysis is based on field notes and semi-structured interviews with volunteers who participated in the activity, either inside or outside of the school district. Two volunteers from different generations were selected as the subjects of the analysis. The selected senior volunteer showed substantial generativity, while the younger volunteer sought to absorb knowledge from the older generation. Through the collaborative practice encouraged by S-sapo, the younger subject adopted practical behaviors generated from the senior subject's job experiences by crossing syntactic boundaries. This phenomenon is called knowledge transfer and is generated from differences in the level of knowledge of the participants. The younger subject also succeeded in adopting perspectives that support these practical behaviors, reinterpreting the senior's perspective, and then applying it to practical contexts by crossing semantic boundaries. This phenomenon of adoption is generated by interactions among contexts. Crossing these boundaries enabled the younger subject to imagine her future from a present perspective. Such illumination of a future path can be regarded as intergenerational learning. By borrowing other people's perspectives in the process of an intergenerational exchange, one is able to envision steps for the future, even if they are somewhat vague. Thus, the intergenerational exchange works as social scaffolding for members of the younger generation.