Chile often portrays itself as Latin America's bridge to Asia, where the ASEAN countries have been singled out as its new priority. Yet, it is not difficult to see that Chile, a small and peripheral state, does not actually serve as a gateway between Latin America and Southeast Asia. This article argues that Chile has lacked consistency in its approach toward Southeast Asia as well as focus of purpose to become a bridge-builder due to the structural constraints faced by a small state. Based on an analytical framework of small states' foreign policies, I revisit Chile's relations with Southeast Asia, pointing to factors driving and limiting deeper engagement with the distant region. The analysis shows that a risk-adverse, low-profile approach of tactical maneuvering has served Chile's objectives even though it is insufficient to bridge the Pacific Ocean. The article concludes with a reflection on this trans-Pacific relationship.