One of the most important issues in modern society is how society modifies the way in which its members develop relationships and foster cooperation in the face of new communication technologies. I explore theoretical and empirical parameters of this process and their implications for encouraging trust and cooperation in negotiations. I begin with an argument for the role of trust and cooperation as part of the foundation of digital commerce by expanding the reach of the social contract theory (ISCT) of Donaldson and Dunfee (1994; 1999). I argue that a digital community is a community in the ISCT sense, and that the basic framework of ISCT can apply to the digital business world. I then analyze the roles of trust and cooperation within this framework, explaining their moral relevance for e-commerce. I follow this discussion with two empirical papers to begin to uncover the nature of digital norms. In "Negotiating with the Millennial Generation" I use a series of behavioral studies and online chat analyses to show that people build trusting relationships online, often resulting in more cooperation than when they talk face to face. I then look at what type of texting creates stronger relationships, showing that longer texting conversations that go beyond small talk generated greater trust and rapport. I also use a behavioral study involving a smartphone application to discuss how over time people learn to use new forms of communication to build trusting relationships through digital media. In the third paper "Why the F*** Don't They TRUST" I develop the notion that particular behaviors can affect online trust development. Using analyses of online texts and additional behavioral studies I show how norm-defying online incivility decreases trust while norm-abiding use of capital letters does not. I show that encouraging people to abide by civility norms develops more trusting and cooperative online environments.