This study examines whether preexisting close friendships facilitate students' cultural agility development during short-term international study abroad experiences. Using a longitudinal design, we found that study abroad students who had a close friend accompanying them on the experience (i.e., an "international study buddy") had lower cultural agility at the onset of the experience but had a higher level of cultural agility development upon return, compared with those without a friend on the trip. Those who did not travel with friends demonstrated no significant cross-cultural competency development. Our findings suggest that contextual novelty is independently determined, and the presence of a trusted friend may help reduce the novelty enough such that students with lower predeparture cultural agility can comfortably gain from the experience. At the same time, for development to occur, students with higher cultural agility may need more contextual novelty than the short-term study abroad experience provides.