Kuwait, a small city-state on the Persian–Arabian Gulf, has undergone massive political, economic, and social development throughout the 20th century. In spite of this, Kuwaiti rulers continue to cherish what is perhaps an impossible dream: that Kuwait can be simultaneously a “developed” country and a “traditional” tribally organized social formation run by an autocratic ruler. This dream is echoed in equally ambivalent pronouncements and policies regarding women, not only by representatives of the state but also by Kuwaiti citizens. Should Kuwaiti women stand side by side with men in public life as half of a modern society, or should they be secluded, subjected by, and submissive to the men in their lives as local “tradition” demands? In this essay I argue that these two ambivalences are linked. Democratization of Kuwaiti political life has proceeded in fits and starts that parallel the uneven progress of democratization of gender relations in Kuwait. Perhaps in consequence, the politics of both kinds of democratization have become more closely linked.