Reflective listening is a core counseling skill that supports effective communication in mental and behavioral health. Understanding how this skill develops over time is critical for designing scalable training and feedback systems.In this paper, we study how counseling trainees develop reflective listening skills over time. Using a real-world dataset of 6,196 trainee responses, we model responses as trajectories in semantic embedding space and apply residual embeddings and similarity-based metrics to quantify week-to-week learning progression.Our analyses reveal systematic changes, including increased semantic alignment and reduced variability, consistent with consolidation of reflective listening skills. We further show that these trajectory patterns are accompanied by subtle linguistic shifts associated with effective counseling practice.