My research looks at the struggle between greater simplicity and greater complexity online conversations. I lay out two different feedback loops that shape online conversations, the Simplicity loop and the Complexity Loop. By online conversations, I am referring to the process by which people come together and decide what means what. Are GMOs good or bad? Is the president a sinner or a rogue? Was the film genius or mad? The first feedback loop, which I will call the Simplicity Loop has three parts that generate each other. 1) A simple conversation becomes 2)popular and 3) generates a consensus which leads to greater simplification. The second loop, which I will call the Complexity Loop also consists of three parts. 1) An intricate and complex conversation 2) breaks into diverging positions 3) generating new ideas and positions. The Complexity Loop generates and recombines ideas, but does not make them popular. I then lay out how to study the two loops using Yule I measure. The measure is a statistical index of linguistic complexity and can be used to study the degree to which online conversations are becoming more simple or complex. I then illustrated the utility of the theory and used the Yule I measure to study conversations on Reddit, an online messaging board.