The first film about the Chicago Cubs world series win and the people who lived through it. A transformative unconventional story blending coming-of-age cinema verite in a deep personal tale of weightloss struggles and love. Based on the true relationships of Chicago natives in the two years leading up to the historic world series win.

Will decides to propose to his friend and hires a cameraman to capture the moment. When the proposal goes horribly wrong, they turn his heartbreak into a comedic documentary. A chaotic whirlwind of self-absorbed actors in NYC.