The psycholinguistic theory of Communication Accommoda-tion proposes that people modify communication dynamics(e.g. vocal patterns, gesture, word choice, syntax, etc.) tominimize (or maximize) their social differences. Research oncommunication accommodation has shown that people whowant social approval will modify their linguistic style to matchthat of their interactant; however, most studies have been con-ducted on small-scale datasets and in laboratory situations. Inthis work, we investigate the relationship between linguisticsyntactic usage and conversation participation in a more nat-uralistic conversational setting: social media conversations onReddit.com. We introduce a novel approach for calculatingdocument-level syntactic similarity by relying on natural lan-guage processing methods (parse tree generators) and graphtheory techniques (minimum weight perfect matching on com-plete bipartite graphs). Using the proposed method, we presentthe results of two experiments which demonstrate that userswho comment on a post tend to use syntax similar to that ofthe original post. Specifically, we provide evidence that com-ments on a post are more likely to follow the syntactic structureof the original post, compared to both random comments andalso posts by the author of the comment.