In general, individuals with lower socioeconomic status (SES) are less physically active and adhere to poorer diets than higher SES individuals. To promote healthier lifestyles in lower SES populations, we hosted a digital health promotion program among male vocational students at a school in The Netherlands. In a pilot study, we evaluated whether this target audience could be engaged with an mHealth app using lottery-based incentives that trigger feelings of anticipated regret. Especially, we studied the social and interpersonal aspects of regret lotteries in a within-subject experimental design. In this design, subjects either participated in a social variant (i.e., with students competing against their peers for a chance at a regret lottery), or an individual variant (i.e., with subjects solely individually engaged in a lottery). Additionally, we studied the impact of different payout schedules in a between-subject experimental design. In this design, participants were assigned to either a short-term, low-value payout schedule, or a long-term, high-value payout schedule. From a population of 72 male students, only half voluntarily participated in our 10-week program. From interviews, we learned that the main reason for neglecting the program was not related to the lottery-based incentives, nor to the prizes that were awarded. Instead, non-enrolled subjects did not join the program, because their peers were not joining. Paradoxically, it was suggested that students withheld their active participation until a larger portion of the sample was actively participating. From the subjects that enrolled in the program (N = 36, males, between 15 and 25 years of age), we found that a large proportion stopped interacting with the program over time (e.g., after roughly 4 weeks). Our results also indicated that students performed significantly more health-related activities when assigned to the social regret lottery, as opposed to the individual variant. This result was supported by interview responses from active participants: They mainly participated to compete against their peers, and not so much for the prizes. Hence, from this study, we obtained initial evidence on the impact of social and competitive aspects in lottery-based incentives to stimulate engagement levels in lower SES students with an mHealth app.