Rising numbers of single middle-aged and older adults encouraged a proliferation of online dating websites targeting this population. However, few studies examine aging adults’ involvement in online dating. This study uses semistructured interviews with 18 online daters aged 53 to 74 and 2 romance coaches to examine how aspects of their online expectations and experiences are shaped by age and gender. Analyses reveal that men seek committed relationships, whereas women desire companionship without demanding caring roles. Different barriers to dating increase the appeal of online strategies: Men face narrow social networks, while women face competition from younger women and friendship norms limiting the pool of eligible partners. Both genders screen for youthful characteristics and attempt to convey youthful images of themselves. Men’s criteria center on physical attractiveness, whereas women’s focus is on abilities. In constructing profiles, women focus on their looks and sociability and men on their financial and occupational successes.