This chapter provides a nuanced look at the romantic and sexual relationships of Port City youth. Popular culture, media, public policy, and academic scholarship alike have pathologized the romantic and sexual relationships of economically marginalized youth of color by constructing their sexualities as “risky,” teen pregnancy as an epidemic in their communities, and men in these communities as predatory. Their romantic and sexual ties are, however, more complex. This chapter highlights the many joys of first love, the heartbreaks of romance, the resources generated within romantic and sexual relationships, as well as the sacrifices people make out of love. It shows how gender ideologies impact the everyday lives of youth, and it highlights how young women manage the pregnancy panic by distancing themselves from risk narratives and from some of their pregnant and parenting peers. They distance themselves by drawing on feminist ideologies of self-development and, in the process, police their own bodies and bodies of their peers, often reproducing dominant race, class, and gender narratives. Drawing on women-of-color feminisms, this chapter argues that the ubiquitous problematization of teen parenthood and sexuality interferes with resources that could be used to support all young people’s educational and occupational goals.