Vision-language models have shown impressive progress in recent years. However, existing models are largely limited to turn-based interactions, where each turn must be stepped (i.e., prompted) by the user. Open-ended, asynchronous interactions, where an AI model may proactively deliver timely responses or feedback based on the unfolding situation in real-time, are an open challenge. In this work, we present the QEVD benchmark and dataset, which explores human-AI interaction in the challenging, yet controlled, real-world domain of fitness coaching – a task which intrinsically requires monitoring live user activity and providing immediate feedback. The benchmark requires vision-language models to recognize complex human actions, identify possible mistakes, and provide appropriate feedback in real-time. Our experiments reveal the limitations of existing state-of-the-art vision-language models for such asynchronous situated interactions. Motivated by this, we propose a simple end-to-end streaming baseline that can respond asynchronously to human actions with appropriate feedback at the appropriate time.