Math anxiety is always just around the corner. At the university, it makes students continuously postpone the Calculus exam, leading them into a vicious circle of low confidence and poor performance. To get out of this situation, students need to be motivated and involved. They also need to master metacognitive strategies that can support their learning process. In this paper, we present a digital activity entitled Advent Calendar, focused on storytelling and proposed through the logic of spacing. The aim is to increase students’ motivation and self-awareness, but also to obtain learning analytics useful to monitor progress and solve any possible weaknesses with appropriate feedback. The activity was proposed using the tools offered by the Learning Management System (LMS) Moodle. It was tested in three university courses at two Italian universities, the University of Milan and the Polytechnic University of Turin, with students’ active participation. This participation had a high impact on the results of the final examination. Feedback demonstrated positive feelings and good results in the motivation process, while the analytics showed a continuous approach to the study of mathematics.