Gunrock is the winner of the 2018 Amazon Alexa Prize, as evaluated by coherence and engagement from both real users and Amazon-selected expert conversationalists. We focus on understanding complex sentences and having in-depth conversations in open domains. In this paper, we introduce some innovative system designs and related validation analysis. Overall, we found that users produce longer sentences to Gunrock, which are directly related to users’ engagement (e.g., ratings, number of turns). Additionally, users’ backstory queries about Gunrock are positively correlated to user satisfaction. Finally, we found dialog flows that interleave facts and personal opinions and stories lead to better user satisfaction.