Ever wondered about homelessness, wanted to learn more about it, and felt like helping the homeless? Engaging Homelessness is your chance to do so! This course examines the multifaceted problem of urban homelessness through service learning, offering students the opportunity to conduct and think about on-site field experiences of working with homeless service and advocacy organizations in New York City within an academic framework. Students work with one of two New York City-based homeless service and advocacy organization -- the Coalition for the Homeless and Women in Need -- for approximately 50 hours during the semester, performing assigned tasks upon negotiating mutually agreeable, flexible schedules (evening volunteer opportunities are possible). Academic coursework conducted online provides discussion of the nature, extent, and causes of, as well as societal and policy responses to, homelessness. The class intends to challenge common stereotypes about homeless people, understand the challenges and constraints homeless service providers face, and think about ways to address homelessness in creative, innovative, and unconventional ways.