Historical studies of prostitution often rely primarily on legal documents, court cases, and police records. These all show points where sex workers encounter the law, and thus focus on the kinds of economically-motivated sexual relations recognized by the state as illegal. The term “prostitution” is rarely defined in these studies, however, leading to the implicit suggestion that it is a clearly defined activity. In fact, there are a wide range of sexual relationships involving a greater or lesser degree of financial quid pro quo. This paper reevaluates the concept of prostitution by examining a variety of types of commercial and quasi-commercial sexual relationships in Turkey (specifically Ankara) in the 1940s and 1950s. Gender roles and gender relationships were still in the process of being redefined by the Kemalist revolution, and for a young sexually active man a wide variety of options presented themselves. Options ran the gamut from brothels and the purely mercenary prostitution they represented all the way to women (especially widows and divorcees) who wanted nothing more than sex. Within that range, though, were also those who would never accept money for sex, but did not mind being given presents, and those who used sex in an attempt to trap a man into marriage. Furthermore, women could be found who, in addition to sexual favors, provided domestic services such as sewing or cleaning. This paper draws heavily on a unique set of (currently unpublished) memoirs describing one man’s experiences with various commercially motivated sexual experiences in Ankara in the late 1940s and early 1950s. These memoirs give us an insider’s view of this world that cannot be derived from legal and administrative discourse and police reports. Of course, they give us primarily the male view of this world, but also, indirectly, something of the women’s perspectives as well. It also draws on recent work on prostitution in the early Turkish republic (such as that of Mark David Wyers, and of Evered and Evered). In addition, it looks at comparable work from earlier periods, such as Ahmet Rasim’s autobiographical work on womanizing in the late Ottoman Empire, as well as works on the subtle shadings of sexual relationships in other parts of the world, such as Elizabeth Clement’s Love For Sale, on World War One-era New York City. Sexual relations in 1950s Turkey went beyond the confines of marriage and state-monitored prostitution. This paper begins to examine their complexity.