Evaluating LLMs' instruction-following ability in multi-topic dialogues is essential yet challenging. Existing benchmarks are limited to a fixed number of turns, susceptible to saturation and failing to account for users' interactive experience. In this work, we propose a novel framework featuring a three-layer tracking mechanism and a query synthesis agent to mimic sequential user behaviors. Grounded in Flow Theory, we introduce process-centric metrics and terminate a conversational evaluation only upon exhausting user patience. Leveraging this framework, we present EvolIF, an evolving benchmark covering 12 constraint groups. Our analysis reveals deficiencies in failure recovery and fine-grained instruction following, with performance stratification becoming evident as conversational depth increases. GPT-5 demonstrates the most sustained resilience, maintaining a 66.40% robustness score, outperforming Gemini-3-Pro by 5.59%, while other models lag behind. Data and code will be released at https://github.com/JiaQiSJTU/EvolIF.