The ability to trust others, including strangers, is a prerequisite for human cooperation. Economically it is not rational to trust strangers, as trust can be easily exploited. Still, generally, the level of trust toward strangers is relatively high. Trust is closely related to trustworthiness: when trusting others, one expects them to reciprocate. Some individuals elicit more trust than others. Apparently, humans use subtle cues for judging the trustworthiness of their interaction partners. Here, we report on an experiment that investigates trust and trustworthiness in a population of 176 mainly Dutch students. The aims of our study were: (1) to investigate how the sex of interaction partners and their facial appearance (femininity/masculinity) affect the degree of trust and trustworthiness, compared to fully anonymous conditions; (2) to test whether individuals who elicit trust in their interaction partners are trustworthy themselves. Each subject of our experiment played five one-shot Trust Games: one with an anonymous interaction partner, and four “personalized” games after seeing a 20 s silent video of their interaction partner (twice same-sex, and twice opposite-sex). The degree of facial sexual dimorphism was investigated with geometric morphometrics based on full-face photographs. Our results revealed that, despite the already high level of trust in the anonymous setting, the personalization of interactions had a clear effect on behavior. Females elicited more trust in partners of both sexes. Interestingly, females with more feminine faces elicited less trust in both male and female partners, while males with more masculine facial shape were more trusted by females, but less trusted by males. Neither sex nor facial femininity/masculinity predicted trustworthiness. Our results demonstrate that (1) sex and sex-related facial traits of interaction partners have a clear effect on eliciting trust in strangers. However, (2) these cues are not reliable predictors of actual trustworthiness.