Herein are considered some digital methods of predicting singularities in social dynamics; specifically, the Schelling’s computer modeling project. An example of modeling is how the preferences for neighbors of the same race eventually leads, over time, to a completely segregated population. A threshold can be set, assuming that after a certain degree of isolation, the singularity phenomenon appears, making both sides alien and malevolent. Similarly, beyond a certain degree of integration, a singularity point may be defined, creating unity and a harmonious community. A practical application of computer modeling is predicting traffic jams or road catastrophes. Red-teaming is a kind of a prestructured roleplay, providing a methodology to explore the uncertainties and challenge of situations associated with cusp catastrophe occurrences. Some participants take on the role of the partners, others of the competitors. Green-teaming represents open situations, also encompassing cooperative and noncompetitive behaviors. It is pursued through real-life roleplaying games, where participants imagine future situations. This way of playing with the future enables combining individual cognition with social interactions and, as a result, leads to potential aggregated outcomes.