Evaluating conversational systems in multi-turn settings remains a fundamental challenge. Conventional pipelines typically rely on manually defined rubrics and fixed conversational context$-$a static approach that limits coverage and fails to capture the diverse, emergent behaviors of dialogue models. To address this, we introduce CoReflect (Conversational Evaluation via Co-Evolutionary Simulation and Reflective Rubric Refinement), which unifies dialogue simulation and evaluation into an adaptive, iterative process. CoReflect employs a conversation planner that generates structured templates to guide a user simulator through diverse, goal-directed dialogues. Subsequently, a reflective analyzer processes these dialogues to identify systematic behavioral patterns and automatically refine the evaluation rubrics. Crucially, the insights from the conversation analysis are fed back into the planner to update conversation templates for subsequent iterations. This co-evolution loop ensures that the complexity of test cases and the diagnostic precision of rubrics improve in tandem. By minimizing human intervention, CoReflect provides a scalable and self-refining methodology that allows evaluation protocols to adapt alongside the rapidly advancing capabilities of dialogue models.