When interpreting the fundamental liberties in the Singapore Constitution, courts presently do not engage in a proportionality analysis – that is, a consideration of whether limitations on rights imposed by executive or legislative action bear a rational relation with the object of the action, and, if so, whether the limitations restrict rights as minimally as possible. The main reason for this appears to be the expansive manner in which exceptions to the fundamental liberties are phrased, and the courts’ deferential attitude towards the political branches of government. This paper considers how the rejection of proportionality has affected the rights to freedom of expression and assembly, and freedom of religion, and argues that although proportionality was originally a European legal doctrine, its use in Singapore is not only desirable but necessary if the Constitution is to be regarded as guaranteeing fundamental liberties instead of merely setting out privileges that may be abridged at will by the Government.