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Gambling usually involves wagering real money but can also be conducted with virtual money, chips, or coins. This phenomenon is sometimes referred to as simulated gambling, social gambling, or play money gambling. This study explores correlations and transitions between simulated gambling and real money gambling with an emphasis on gambling-related harms and public health concerns. The analysis is based on a national representative survey of 46,136 German Internet users which included 5,191 real money online gamblers (RMG), 54% of whom had also participated in simulated gambling (SG). The data set is divided into subsamples based on participation in SG to carve out significant differences in these groups in regard to various socio demographics, gambling patterns, and gambling problems. Regression models are used to predict RMG frequency, participation in SG, SG participation frequency, and problem gambling. The results show a clear proximity between SG and RMG with 17% of the total sample and 54% of problem gamblers reporting being "quite sure" or "certain" that simulated gambling had led them to gambling with real money. While 7% of individuals that engaged exclusively in RMG showed gambling problems, the rate is 33% for those that engaged in both RMG and SG. Regression results provide further evidence of a relationship between SG and problem gambling, although with differing effect sizes for different game forms. We argue that SG can be both a substitute and a primer for RMG, especially for problem gamblers.