Users often feel regret after using social media, making regret a more ecologically valid target than screen time for understanding when phone use becomes problematic. Existing self-monitoring tools cannot anticipate regret before it occurs, and prior physiological work on social media use has been confined to the lab with research-grade sensors and curated content, leaving the question of in-the-wild prediction open. We deployed a 7-day in-the-wild experience sampling study with 21 participants, combining passive smartphone logging, a low-cost consumer smartwatch (Bangle.js 2, \$80), session-level surveys (1,445 sessions), and exit interviews to investigate when and why social media sessions become regretful, and whether regret can be anticipated before a session begins. Three findings stand out: (i) the gap between intended and actual use predicts regret far more strongly than session duration, with duration's apparent effect collapsing once intention is modeled; (ii) regret is amplified when sessions displace a valued alternative, particularly at night and following productivity-app use; and (iii) pre-session contextual features generalize across participants while physiological signals add person-specific lift, pointing toward a two-layer architecture for just-in-time adaptive interventions. Interview themes of scrolling-as-avoidance and time blindness contextualize these patterns and surface design opportunities beyond timer-based interventions.

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