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The tumultuous relations between the Islamic Republic of Iran and the West, in particular the United States, since the 1979 revolution is climaxing in the dispute over Iran’s nuclear development. However, if as expected, a settlement is reached, mainly by Iran backing down, an important question would loom on the horizon: Can the West, and principally Washington, live happily and peacefully with a theocracy that is ideologically radical in character and anti-American in orientation? This essay deals with that question and explores pathways that may lead to some answers. In so doing it will point out the root causes of the hostility of the clerical establishment towards the United States and why despite various attempts and strong incentives a thaw in relations has eluded both capitals. Significant internal and external factors will be highlighted in this regard and how they may perceivably give (or not give) way to the resumption of diplomatic ties between Iran and the United States will be investigated.