This paper explores different modes of singlehood through the lives of three elite men. There is a brief discussion of single women mentioned in the epistles of one of the three: Libanius, a 4th century professor of rhetoric in Antioch. The women in question are widowed mothers of his students, most of whom did not remarry and who experienced certain struggles as a result, as well as their status having consequences for the students in question. But there are few details and Libanius’s concern is primarily for how their status affected their sons.