The present study investigated the dating experiences of single women living with multiple sclerosis (MS). The present research used a mixed methods approach, with the quantitative component examining the role of disability severity, insecure attachment (avoidant and anxious), age, illness duration, depression, body esteem, sexual esteem, and attractiveness on dating experiences among 99 single women living with MS. Participants were recruited through MS societies in Canada and the United States. Regression analyses showed that overall, greater disability severity, longer illness duration, greater insecure attachment, lower sexual esteem and lower perceived attractiveness were predictive of worse dating experiences and more barriers to dating. Dating experiences were similar across ages. The second component of the study consisted of qualitative interviews with 12 women (half in a younger and half in an older age group), which were completed individually by telephone. The qualitative approach borrowed from a phenomenological lens and interviews were coded to explore the dating experiences of the women. Across the younger and older age groups, participants identified barriers to dating, coping strategies, negative cognitions about dating with MS, concerns regarding disclosure of MS, and impact of MS on body and sexual esteem. Some age related differences in dating were noted, such as concerns about pregnancy. The current research highlights the importance of conducting further research into the impact of MS on dating and in exploring potential interventions to help support women many of whom endorsed encountering various barriers to dating when living with MS.