We present Re:Member, a system that explores how emotionally expressive, memory-grounded interaction can support more engaging second language (L2) learning. By drawing on users' personal videos and generating stylized spoken questions in the target language, Re:Member is designed to encourage affective recall and conversational engagement. The system aligns emotional tone with visual context, using expressive speech styles such as whispers or late-night tones to evoke specific moods. It combines WhisperX-based transcript alignment, 3-frame visual sampling, and Style-BERT-VITS2 for emotional synthesis within a modular generation pipeline. Designed as a stylized interaction probe, Re:Member highlights the role of affect and personal media in learner-centered educational technologies.

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