In Jordan, the average age of first marriage has increased in recent years. Current trends suggest the number of women between the ages of who have never been married has also been increasing. Therefore, heterosexual women are spending longer and longer portions of their sexual and reproductive lives unmarried, leading to changes in women’s sexual behaviours. Jordanian women are increasingly having multiple sexual partners prior to marriage and are engaging in casual sexual relationships. These changing dynamics have significant social and health implications. Drawing from longstanding ethnographic fieldwork in Amman, this chapter explores contemporary dating practices in this setting. Women’s narratives suggest that they are balancing competing sexual and social desires and navigating a number of peer, familial, and societal pressures and logistical issues. From “hooking up” in cars in dark alleys, to renting out apartments by the hour, women continue to find creative ways to explore their sexual desires clandestinely; however, with little to no sexual education, practicing safe sex still remains an issue. Accounts from women in Jordan reveal the important role that technologies, such as WhatsApp, social media accounts, and dating applications, play in identifying casual partners in ways that are socially protective. I conclude with some reflections on how existing sexual and reproductive health services might better meet women’s evolving needs.