Sustained emotional support is a long-horizon interaction task closely tied to human well-being. Recent research demonstrates generative agents' capacity for momentary emotional support, yet how these capabilities sustain support over time remains unclear. To examine this challenge, we deployed PAIR, a theory-based emotion-regulation companion, with 19 participants for 14 days. Across 1,093 sessions, we paired emotion estimates with self-reports before and after guidance and analyzed logs and interviews. Estimates corresponded more closely to self-reported valence and dominance than arousal. Guided conversations were followed by higher valence and state-dependent arousal changes. Participants felt understood through contextual exploration and emotional acknowledgment, acting on guidance suited to their needs and constraints. Perceived helpfulness of guided conversation significantly increased over time. Our findings link memory updates and retained corrections to cross-session personalization, informing future emotional support tools that adapt to evolving needs, learn from prior outcomes, and preserve user control over memory.

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