The study concerns the development of compensative and compulsive buying in Poland comparing the results of three waves of a cross-sectional study conducted before and at the end of the COVID-19 pandemic. Six predictors of susceptibility to compensative and compulsive buying are in focus: materialism, self-esteem, gender, age, frequency of online shopping, and experience of the COVID-19 pandemic. However, the importance of the first four predictors in explaining compensative and compulsive buying is already very well described in the literature, while the novelty consists in the predictive model including the variables that describe frequency of online shopping and negative experiences related to the COVID-19 pandemic, such as coronavirus infection, hospitalization or death of a loved one. On the one hand, a stronger susceptibility to compensative and compulsive buying could be a reaction to these negative experiences of the pandemic; on the other hand, the increased frequency of online shopping as a result of the pandemic may be an important factor in the development of compensative and compulsive buying due to the easy implementation of purchase acts and weaker social control. To achieve the above research objectives, the German Compulsive Buying Indicator (GCBI) was used to measure susceptibility to compensative and compulsive buying. The data were obtained within three waves of the study (2010, 2019, 2022) based on a random sample of about 1,000 respondents representing statistically the general adult population. Drawing on this study, the prevalence of compensative and compulsive buying is observed at 12–19% and 2–4%. The predictors of GCBI are materialism, self-esteem, gender in all examined models and additionally age, frequency of online shopping, and experience of the COVID-19 pandemic in selected models. Although the findings related to the role of materialism, self-esteem, and gender in the prediction of GCBI reflect the results reported in the literature, the analogous conclusions about age, online shopping, and experiences with the COVID-19 pandemic are different from the established opinions. The commonly reported effect of age becomes statistically significant when the examined population is limited to Gens Y and Z. Although extensive online shopping co-exists with compensative and compulsive buying in the total population, the obtained data lead to reverse conclusions in the case of women’s subpopulation representing Gens Y and Z. The negative experience with the COVID-19 pandemic operationalised as hospitalization of a close friend predicts GCBI, but again only in the case of representatives of Gens Y and Z, especially among women. The findings show how important the creation of appropriate intervention strategies is within the consumer policy directed to representatives of the younger generations who may develop pathological buying as a response to negative experiences such as COVID-19 pandemic. The findings can inform of the goals behind therapeutic support for compulsive buyers, and implications for social work. People affected by excessive compensative or compulsive buying need to be given opportunities to build up their strengths and growth of their psychological resources towards healthy self-esteem, which seems to be the best protection against excessive compensative and compulsive buying.