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This study examined parental and peer attachments and their relationship to entitlement attitudes and subjective well-being among a sample of affluent adolescents. We sought to integrate the perspectives of both clinical and social psychology in examining entitlement attitudes, ranging from healthy to narcissistic. This was accomplished by using a new method of assessing entitlement from the social psychological perspective and comparing entitlement attitudes to attachment. Attachment was measured in terms of trust, communication, and alienation in relationships with parents and peers. Stereotypes of the affluent were explored. Findings showed that adolescents reporting higher levels of alienation from, and lower levels of trust in, primary attachment figures, also indicated higher levels of narcissistic entitlement. By contrast, less alienation from parents and peers, and greater well-being was associated with healthier entitlement. Attachment was shown to be a better predictor of entitlement attitudes than perceived level of wealth. Thus the stereotype that entitlement, particularly narcissistic entitlement, is linked to the wealthy was unsupported.