While intuition suggests and much research has shown that people are attracted to advantaged individuals, the present study explored the conditions under which people might be attracted to disadvantaged individuals. We hypothesized that perceiving someone as unfairly disadvantaged can motivate attributions of positive personal characteristics and, consequently, judgments of heightened attractiveness. Seventy-eight participants were randomly assigned to read about a job applicant facing a fair or an unfair application process resulting in a competitive advantage or disadvantage. In support of our hypothesis, participants judged unfairly disadvantaged applicants (i.e., underdogs) and fairly advantaged applicants as more physically attractive and suitable as dates compared with fairly disadvantaged and unfairly advantaged applicants. These results highlight the role of situational factors in judgments of one’s attractiveness.