This work addresses a crime that emerged in Costa Rica between the 1970s and the early 1990s, known as the “timo del amor” (love swindle). It consisted of frauds with erotic connotations in which the victims were men deceived before, during, or after engaging in casual sexual encounters. The aim of the study is to recover this history in order to invite reflection on the characteristics that distinguished men and women at that time, and to highlight an ambiguity in gender roles that emerges from the news stories examined. The research is based on a review of the crime section of the newspaper La República during the mentioned periods, with the goal of reconstructing the informational framework in which these stories circulated and understanding the narratives surrounding them. The analysis relies on consulting journalistic archives from the newspaper, focusing on crime reports that documented these cases across the indicated decades. From this source, the study identifies patterns of representation and determines how the plots of the “love swindle” were constructed within the news, referring to the scenes of encounters and the people involved. The approach seeks to explain, on the basis of the reviewed material, how the journalistic descriptions articulated concepts of sexuality, masculinity, and femininity, and how these elements contributed to a social vision of criminal reality and of behaviors considered acceptable or dangerous. In the conclusions, the study examines recurring ideas about these crimes, which portrayed men as impulsive and, at the same time, naïve, while women were described as cunning and uninterested in traditional sexual morality. These repeated representations suggested the dangerousness of any woman who showed interest in patterns of casual sex, and they indicate how media coverage could have reinforced gender stereotypes while simultaneously justifying social fears about female autonomy in intimate spheres. Thus, the work proposes a critical reading of journalistic sources to understand how the news narratives of the time contributed to constructing supposed limits and risks associated with female sexuality and male behavior in contexts of courtship and deceit.