This article is based on a study of older Canadian widows, supplemented by ongoing work with widowers. Twenty-eight in-depth interviews were conducted in New Brunswick with women over fifty whose husbands had died within the past seven years. Most of the widows did not wish to remarry because they felt they had already had the best possible husband, had suffered with his loss, and did not want to schedule their lives around a new husband. Cautionary tales about the risks of remarriage were widespread. Norms regarding interactions between men and women are ambiguous, the motives of men are not always clear, and changed sexual mores present challenges as do the reactions of adult children to a potential relationship. Widows often need to find creative new ways to interact safely with men in order to avoid misunderstandings both about their interest in remarriage or their desire or lack of desire to engage in intimate activity. The article includes a discussion also of widowers’ attitudes towards repartnering.