Despite historical and religious ties, geographical proximity, and other opportunities for mutual benefit, the overall relations between Ethiopia and the Gulf Cooperation Council (GCC) countries have remained ambivalent for many years. This study examines Ethiopia's economic and political relations with the Gulf countries since 2000 and the challenges that hindered and opportunities that can further improve their relationship. The study argues that while their economic relations have been developing steadily over the past two decades, especially since the political transition in Ethiopia in 2018, their political relations remained weak. Their relationship is not based on evenly balanced mutual dependence; rather it is asymmetric as the Gulf countries are relatively less dependent in the interdependence relationship. The study also finds out that the perception of the Gulf countries' elites considering Ethiopia as a Christian empire and Ethiopian elites' skepticism of the Arab world due to past hostile political relations; the GCC countries' support of Egypt in the Nile disputes; and mistreatment of Ethiopian migrants in some GCC countries are among the key challenges undermining their relations.