In this paper, I argue that scholarship has yet to thoroughly engage with the ways in which change in globalizing India is predicated upon and produces linkages between the urban and the rural. As a corrective, I attend to some examples of the psychosocial changes that increased rural-urban connectivity might beget, in relation to how those who live in the village might imagine the city itself. These imaginings of the city, a constitutive aspect of the rural imagination in 21st Century India, affect how those living in villages conceive of their potential futures. This psychosocial register is one way to assess how the urban and the rural are experienced simultaneously as linkage and divide by those living in India’s villages today. I make my claims based on ethnographic data gathered over a two-year period beginning in March 2013 with a group of students living in Adavisandra, a village approximately 40 kilometers outside of Bangalore, Karnataka, one of India’s most rapidly urbanizing cities. I focus on one specific event that occurred during my fieldwork, a trip to Bangalore with five of my participants, which revealed both their own rural-urban aspirations as well as, inadvertently, the anxiety that rural-urban connection produced in their families and community.