In today's fast-paced world, accurately monitoring stress levels is crucial. Sensor-based stress monitoring systems often need large datasets for training effective models. However, individual-specific models are necessary for personalized and interactive scenarios. Traditional methods like Ecological Momentary Assessments (EMAs) assess stress but struggle with efficient data collection without burdening users. The challenge is to timely send EMAs, especially during stress, balancing monitoring efficiency and user convenience. This paper introduces a novel context-aware active reinforcement learning (RL) algorithm for enhanced stress detection using Photoplethysmography (PPG) data from smartwatches and contextual data from smartphones. Our approach dynamically selects optimal times for deploying EMAs, utilizing the user's immediate context to maximize label accuracy and minimize intrusiveness. Initially, the study was executed in an offline environment to refine the label collection process, aiming to increase accuracy while reducing user burden. Later, we integrated a real-time label collection mechanism, transitioning to an online methodology. This shift resulted in an 11% improvement in stress detection efficiency. Incorporating contextual data improved model accuracy by 4%. Personalization studies indicated a 10% enhancement in AUC-ROC scores, demonstrating better stress level differentiation. This research marks a significant move towards personalized, context-driven real-time stress monitoring methods.