World Wide Web technologies create fundamentally new potentials for social interaction and decision-making among diverse social actors. A new generation of Web technologies, accompanied by new political cultures, portends an ushering of radical transformations in democratic decision-making. This chapter asks three critical questions: (1) How do emerging Web technologies deepen democratic participation? (2) How do we avoid or transform scenarios where Web technologies are employed to maintain political-economic oligarchies of power? and (3) What new political cultures or political contracts may emerge through the convergence of Web technology and political engagement? This chapter uses the recent precedent of Liquid Democracy online decision-making experiments in Germany, to answer these questions and peer into the futures of governance. The study came to the following conclusions: (1) We are witnessing a shift from formal representative democracy to situational and fluid forms of governance; (2) Alongside this we are seeing a deepening of political participation, which may bring forth new political cultures and political contracts; and, (3) A number of possible scenarios emerge from the decline of formal representative democracy—A possible “Liquid Revolution” where online governance has transformed democracy; a “Steady-state Oligarchy” where pseudo-representative and oligarchic powers persist; a “Partner State” where representative and online variegated governance is blended; and a “War of the Worlds” where statist and variegated governance online systems aggressively compete for power.