In the 1930s influential ‘secular’ Egyptian thinkers like Taha Husayn and Muhammad Husayn Haykal turned to religious themes and Islamic history as part of their intellectual and political agenda, prompting Western scholars to speak of a ‘crisis of orientation.’ This judgment was challenged by a later generation of scholars who rejected a strict religious-secular binary and argued for a deeper understanding of popular discourse. Egypt’s liberals, they insisted, were not abandoning core ideals – they were promoting them in ways that might be characterized as inclusive of religious reformism. This paper will explore the ideological roots of a new liberal ‘crisis of orientation’ – one in which liberal voices appear to have adopted a more myopic binary between secular and religious paths toward democratic politics, and in so doing have contributed (not solely but significantly) to the fracturing of the January 2011 coalition that brought down Hosni Mubarak and – for a time – Egypt’s autocratic regime, and contributed to the polarization the marked the period between January 2011 and June 2013, and that which has followed. I focus on two influential public voices of the ‘liberal’ opposition, the comic Bassem Youssef and writer Alaa al-Aswany. Each faced a new public sphere in which rules had changed and political grounds shifted. Youssef’s meteoric rise and fall is the story of a suddenly open media with unprecedented freedom to pillory the ruler – one who happened to be an Islamist. His comic-satirical oeuvre warrants critical examination in terms of his stand vis-à-vis an elected government (however popular it may or may not have been). Aswany, a dynamo of the emergent anti-Mubarak movement and ‘hero’ of Tahrir Square, has been posited inside – and especially outside – Egypt as a moral spokesperson for democracy. His championing of popular dissent against the Morsi government and later validation of the reassertion of military rule may well be a cautionary tale for those who seek to move Egypt forward towards a true pluralism. To understand the present liberal ‘crisis’ we must, I argue, look to opportunities found and lost, and the fears (founded or not) that drove a wedge between secular and religious oriented forces for change.