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Longitudinal experiential data offers rich insights into dynamic human states, yet building models that generalize across diverse contexts remains challenging. We propose ConText-LE, a framework that systematically investigates text representation strategies and output formulations to maximize large language model cross-distribution generalization for behavioral forecasting. Our novel Meta-Narrative representation synthesizes complex temporal patterns into semantically rich narratives, while Prospective Narrative Generation reframes prediction as a generative task aligned with LLMs’ contextual understanding capabilities. Through comprehensive experiments on three diverse longitudinal datasets addressing the underexplored challenge of cross-distribution generalization in mental health and educational forecasting, we show that combining Meta-Narrative input with Prospective Narrative Generation significantly outperforms existing approaches. Our method achieves up to 12.28% improvement in out-of-distribution accuracy and up to 11.99% improvement in F1 scores over binary classification methods. Bidirectional evaluation and architectural ablation studies confirm the robustness of our approach, establishing ConText-LE as an effective framework for reliable behavioral forecasting across temporal and contextual shifts.