One of the debates about media usage is the potential harmful effect that it has on body image and related eating disturbances because of its representations of the “ideal body”. This study focuses on the drive for thinness among the visitors of various health-oriented websites and online platforms because neither has yet been sufficiently studied in this context. Specifically, this study aims to bring more insight to the risk factors which can increase the drive for thinness in the users of these websites. We tested the presumption that web content internalization is a key factor in this process, and we considered the effects of selected individual factors, specifically the perceived online social support and neuroticism. We utilized survey data from 445 Czech women (aged 18–29, M = 23.5, SD = 3.1) who visited nutrition, weight loss, and exercise websites. The results showed a positive indirect link between both perceived online social support and neuroticism to the drive for thinness via web content internalization. The results are discussed with regard to the dual role of online support as both risk and protective factor. Moreover, we consider the practical implications for eating behavior and weight-related problems with regard to prevention and intervention.