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Psychological stress is a key driver of short-term blood pressure (BP) elevations and cardiovascular risk, yet its moment-to-moment impact in daily life remains difficult to predict. In this longitudinal observational study, we collected multimodal data from 20 adults with self-reported hypertension, including continuous wearable-derived heart rate and activity, ecological momentary assessment (EMA) stress ratings, and ambulatory BP measurements in free-living conditions. The dataset comprised 3694 EMA responses and 3812 BP measurements collected over approximately four weeks per participant (mean 24.1 ± 8.5 days). We evaluated whether participant-specific ("personalized") models outperform a single pooled population model. Two prediction tasks were examined: (i) prediction of near-term BP elevations from wearable signals and stress EMA responses and (ii) prediction of self-reported stress from wearable signals and BP. Across both tasks, personalized models consistently improved predictive performance. For BP prediction, personalized models achieved a mean AUROC of 0.803, exceeding the population model by 0.235, while for stress prediction they achieved a mean AUROC of 0.849, exceeding the population model by 0.208. These findings suggest that personalized wearable-based models can capture individual patterns of stress and BP dynamics, with direct implications for precision mental health assessment and just-in-time adaptive intervention design in future work.