Lifelong digital companions must integrate cross-session cues, continually update their understanding of users, and adapt to shifting privacy boundaries. Existing evaluations fail to capture this, testing memory recall and short-term empathy in isolation. To bridge this gap, we introduce \benchmark, a benchmark centered on multi-session \textit{Memory-Emotion-Environment} loops. By modeling users as persistent worlds with layered profiles and event trajectories, \benchmark uses multi-agent simulation to project environmental dynamics into dialogue, preserving the critical gap between latent thoughts and observable expressions. Evaluating 2,000 personas and 111K tasks across memory tracking, user understanding, privacy control, and emotional companionship, our experiment results reveal a stark reality: even models that saturate current memory benchmarks fail to sustain accurate user understanding and true companionship over long horizons.