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Democratic politics should ideally empower people to talk, engage, and act with one another to shape possible collective futures. The collective ideals and aspirations that sustain our capacity to act in concert with others and form collective wills rely thus on a sense of hope grounded in the open-endedness of politics. In practice, however, political institutions appear limited in their capacity to engage with uncertain futures and the unpredictability of politics, which accentuates, instead, cynicism and apathy. The complexity and contingency of collective expressions of hope in politics raise the question of how to theorize their relationship with future-regarding democratic politics. I propose to address this overlooked question in democratic theory by turning to the literature on hope and its connection with deliberative democracy and democratic innovations. In doing so, I theorize a type of hope associated with a particular collective activity and experience that intersects with future-oriented collective agency and problematizes the capacity of democracy to develop the institutions and practices that sustain this sense of possibility. I first consider how we engage with the future before turning to deliberation as a practice allowing people to coordinate and navigate uncertainty with others. I argue that this political activity generates what I call deliberative hopes by developing the necessary language and shared understandings through which we can collectively assess the present and imagine futures. These hopes bridge the gaps between where we are and where we could go and are constantly actualized by the actions we undertake with others. In turn, they constitute a political good that sustains our collective engagements. As defining forms of collective futures is inherently political, hope represents thus a site and an object of politics. Using the problem-based approach to democracy, I illustrate this duality in democratic systems by turning to the example of climate assemblies. Climate assemblies use deliberative processes to co-constitute a collective orientation amidst the uncertainties and growing anxieties that the climate crisis and its political response generate. They are one example of a democratic innovation that problematizes our relationship with different possible futures and their implications on how we engage with others and the world. Considering the multiple forms of hope, the problem-based approach locates its deliberative expression in relation to the normative function of forming collective agendas and wills. Assessing the activity of hoping with others in democratic politics from a systemic perspective allows us to explore questions of power dynamics, the political constitution and re-constitution of the collective, and the interaction between multiple sites of politics. As such, I argue that connecting the scholarships on hope, deliberative democracy, and democratic innovations contributes to expanding our understanding of both the political implications of hope and the future-regarding dimension of democratic politics.