The aim of this article is to compare the cultural-historical events and decisions regarding how to deal with the higher risks of HIV in MSM, and more specifically, gay populations in Sweden and the Netherlands. A narrative literature was used, based on 46 scientific articles and 20 additional semi-scientific resources. The themes of the arrival of HIV and AIDS, blood donations, offender/victim, the balance of risks with respect to the statistical probabilities and the human factor, and finally, prevention were discussed. It is concluded that certain context-specific historical events (the Dutch Bloody Sunday and the Swedish gay sauna ban) and culturally determined processes (trust in others in the Netherlands, and disapproval of casual sex in Sweden) have led to some important differences in how HIV and AIDS and the higher risks for gay men and MSM have been dealt with. In the Netherlands, there is a stronger protective attitude when it comes to the freedom and autonomy of MSM both when it comes to decisions about sexual behavior and to sharing any positive HIV status. In Sweden, on the other hand, there is a stronger tendency to enforce informing others of their HIV status. In both countries, despite efforts to prevent this, HIV has increased stigma for gay men and other MSM.