Cross-cultural living is accompanied by a myriad of stressors that precipitate coping responses of assimilation (reliance on pre-existing methods) and accommodation (development of new ones). Utilizing a quantitative, longitudinal design, the study examined whether assimilation or accommodation was more effective in enhancing adjustment of 155 Taiwanese students studying in the United States. Specifically, social affiliation with Taiwanese (assimilation) and Americans (accommodation) during their second semester of study was hypothesized to mediate the impact of pre-departure personality on functional adjustment and emotional well-being in the third semester, controlling for acculturative stressors encountered in the first semester. Multivariate analyses showed that affiliation with Americans partially mediated the effect of extroversion on functional adjustment, supporting the effectiveness of accommodation. In addition, extroversion diminished depression level while acculturative stressors reduced functional adjustment and well-being. Finally, women enjoyed more intercultural relationships than men. Altogether, these findings suggest the utility for orientation programs that involve American peers to assist with cross-cultural adjustment, particularly for Taiwanese men.