Where Are We Going With This? depicts two University students meeting on a bench at 2am after a bad night out. This touching two-hander follows the two students' struggles to open up to one another, exploring the awkward comedy and profound intimacy that can occur in those one-off conversations with a stranger.

They flirt, fight, and fumble along a tightrope walk of social norms and personal boundaries, discussing their outlook on the future, their bouts with loneliness, and, eventually, why they ended up on a bench in the middle of the night.

He is a quick-witted and jovial pessimist. She is a distrusting, cynical optimist. Together, they bring out the ugliest and most tender parts of one another as they learn that often, the hardest part of opening up to a stranger is enduring the silence that follows.