Character judgments, based on facial appearance, impact both perceivers' and targets' interpersonal decisions and behaviors. Nonetheless, the resilience of such effects in the face of longer acquaintanceship duration is yet to be determined. To address this question, we had 51 elderly long-term married couples complete self and informant versions of a Big Five Inventory. Participants were also photographed, while they were requested to maintain an emotionally neutral expression. A subset of the initial sample completed a shortened version of the Big Five Inventory in response to the pictures of other opposite sex participants (with whom they were unacquainted). Oosterhof and Todorov's (2008) computer-based model of face evaluation was used to generate facial trait scores on trustworthiness, dominance, and attractiveness, based on participants' photographs. Results revealed that structural facial characteristics, suggestive of greater trustworthiness, predicted positively biased, global informant evaluations of a target's personality, among both spouses and strangers. Among spouses, this effect was impervious to marriage length. There was also evidence suggestive of a Dorian Gray effect on personality, since facial trustworthiness predicted not only spousal and stranger, but also self-ratings of extraversion. Unexpectedly, though, follow-up analyses revealed that (low) facial dominance, rather than (high) trustworthiness, was the strongest predictor of self-rated extraversion. Our present findings suggest that subtle emotional cues, embedded in the structure of emotionally neutral faces, exert long-lasting effects on personality judgments even among very well-acquainted targets and perceivers.