This study presents an ethnographic approach to unpack the differences in digital media use, illustrating how these differences can be better understood as a negotiable quality of incessant action and interaction, rather than as a given quality of social life mandated by the individualism/collectivism dichotomy. Drawing on ethnographic interviews with seven Taiwanese sojourners in the United States and five Americans in Taiwan, this study asked informants to retrospectively recount their sojourning experiences regarding the use of multimedia messaging services (MMS), which presently often involve smartphones. Taiwanese sojourners exhibited stronger family ties than their American counterparts. Instead of relying on collectivistic/individualistic traits as an explanatory mechanism, this study identifies three themes from the life narratives of both groups of sojourners that could explain the observed cultural differences in the terrain of smartphone communication: first, the economic basis on which sojourning was organized was asymmetric between the two groups; second, parents of the two groups had asymmetric knowledge of the sojourning destinations, and this impacted conversational repertoire; and third, the intersection of gender and media constructions of sojourning destinations also shaped varying degrees of bonding. The larger asymmetric structural context at a macro-level may offer fertile ground for further theorization on cultural differences and commonalities.