This work aimed to study the effect of confinement on weight and lifestyle using the Wakamola chatbot to collect data from 739 adults divided into two groups (341 case-control, 398 confinement). Nutrition score (0–100 scale) improved for men (medians 81.77–82.29, p < 0.05), with no difference for women (medians 82.29 in both cases). Both genders reduced the consumption of sweetmeats and sugared drinks ( p < 0.01); men increased their consumption of vegetables, salad, and legumes ( p < 0.01). Both genders reduced their physical activity score (men 100–40.14, p < 0.01, women 80.42–36.12, p < 0.01). Women sat less hours/week, men’s medians 28.81–28.27, women’s medians 35.97–23.33, p = 0.03. Both genders slept longer (hours/day), men 7–7.5, women 7–8 ( p < 0.01) (medians). Their overall health score was significantly reduced (men 85.06–74.05, p < 0.01, women 84.47–72.42, p < 0.01), with no significant weight difference in either gender. Wakamola helped to contact participants and confirm changes in their lifestyle during confinement.