Plan and situated action relationship has been an active area of debate in recent years in various fields of study yet such relationship has a propensity for ambiguity. It would be a limited/desperate argument to claim that plans can capture every level of detail. Needless to say, a model cannot exceed or equal reality. Given that a clear mismatch/incongruence or gap exists between plans and actual events, how do people experience this gap and how do they act accordingly? The proposed framework integrates the field theory of the here-and-now action developed by Kurt Lewin (1936), with both the prototype and basic-level category theories developed primarily by Rosch (1978). Lewins theory captures the dynamic properties of situations whereas Roschs categorization theories capture typifications of the human experience. More specifically, plans are conceived as an activity category-set of possibilities of some future events by which plans have categorical relationships with future actions.