The research conducted by the author in May 2017 (n = 1091) highlights an increased social distance from homeless adults in the Republic of Moldova. Research conducted in 2020 (n = 1201) confi rms the greater social distance from homeless people in Moldova. At the same time, according to the results of the 2017 survey, a high proportion of respondents showed their willingness to help a homeless person if s/he asked for help. This article seeks to explain this contradictory fi nding by triangulating it with three sets of data: (1) the social representation of the respondents towards the homeless in their society, (2) the representation of the homeless in print and visual media in the country (20102016), and (3) the state policies in the last decades towards the homeless. The article concludes that the greater social distance towards and the willingness to help homeless people shared by the participants in our research are analogous to the contradictory media representation (with philanthropic and stigmatizing signifi cance) and the binary character (repressive and assisting) of state policies towards homeless persons in the recent decades.