Communication is an intricate dance, an ensemble of coordinated individual actions. Imagine a future where machines interact with us like humans, waking us up in the morning, navigating us to work, or discussing our daily schedules in a coordinated and natural manner. Current interactive systems being developed by Apple, Google, Microsoft, and Amazon attempt to reach this goal by combining a large set of single-task systems. But products like Siri, Google Now, Cortana and Echo still follow pre-specified agendas that cannot transition between tasks smoothly and track and adapt to different users naturally. My research draws on recent developments in speech and natural language processing, human-computer interaction, and machine learning to work towards the goal of developing situated intelligent interactive systems. These systems can coordinate with users to achieve effective and natural interactions. I have successfully applied the proposed concepts to various tasks, such as social conversation, job interview training and movie promotion. My team's proposal on engaging social conversation systems was selected to receive $100,000 from Amazon Inc. to compete in the Amazon Alexa Prize Challenge (https://developer.amazon.com/alexaprize).