Birds of a feather—the principle of homophily—is robust across cultures, and cultural homophily or the tendency to prefer connecting with those from the same compared to different cultural origin can be especially salient in intercultural contexts. How does cultural homophily relate with cross-cultural adaptation among sojourners? We investigated this question by analysing two sets of longitudinal data collected from international students in Australia. In Study 1 (N = 108), higher cultural homophily at T1 was associated with more acculturative stress as well as more negative affect several months later (T2), controlling for T1 adjustment and demographic variables. This suggested that cultural homophily may exacerbate sojourners’ negative adjustment. In contrast, T1 sociocultural skills were associated with higher heterophily or tendency to favour local Australian ties over other ties at T2. This link was replicated in Study 2 (N = 59). Further in Study 2, negative affect at T1 was associated with subsequent lower heterophily whereas acculturative stress at T1 was associated with higher homophily at T2. Thus, negative adjustment during sojourn may lower openness. In sum, negative adjustment and higher homophily showed predictive relationships in both directions, whereas sociocultural skills seem to enhance the development of stronger ties with local friends.