People in midlife are having sexual relationships outside hetero-monogamy and marriage which contribute positively to their wellbeing. For rural people who are in a non-traditional relationship, confidentiality, access to sexual health services, and stigma are concerns. In this qualitative research project we investigate the experience and wellbeing of 22 rural baby boomers who had a friends-with-benefits relationship within the previous five years. A fear of judgement about their sex lives for some led to a need for secrecy and concern about being seen with partners. Use of health services for sexual health was mixed: many would not ask for testing and some who did were challenged or refused. Four participants' experiences are the focus of this article. Recommendations are made for policy, health practitioner education, clinical guidelines, sexual health promotion, and informal community activities to promote good sexual health and relationship wellbeing for people in midlife.