Recommender systems are widely used in modern lives and contribute to many industries. Therefore, methods to evaluate and improve them are important. Nowadays, much research has been done to improve the system aspects such as algorithms. However, user experiences are not only affected by the systems but heavily rely on the context when using the systems. Therefore, the research on user aspects to understand their experiences is as important. This study contributes an approach that uses collaborative reflection to find insights into users' experiences with recommender systems. Using this approach, this study presents the influences of context on user experiences with recommender systems. This study investigates the importance of situational and personal contexts like mood, time, and location in shaping user satisfaction with recommendations. The research adopts a method based on collaborative reflection, where participants engage in tasks using their YouTube watch history, paired with another individual for real-time discussion. By analyzing contextual influences and the values users wish to achieve, the study identifies key patterns in user behavior and insights into personal preferences. This research not only contributes to the evaluation of recommender systems but also highlights the need for systems to align with both the goals of users and broader societal values. The usability of the proposed method was tested to be successful in crowdsourcing, yielding practical implications for future evaluation and improvements of recommender systems.