James Keating, David Connelly, Matt Smith, and Riley Shaunessy are four high school friends struggling to sort out adulthood in their thirties. One night at their local pub, Jack Taft, a professor of Shakespeare, interrupts their typically inane conversation. Taft begs the foursome to discuss something more consequential than the outcome of a basketball game. Connelly challenges Taft to an impromptu debate. Before any of them have time to marvel at Connelly's intellect, Taft leaves a mysterious envelope for Keating, daring these friends to chase one of the greatest mysteries in the history of the English language: who was William Shakespeare? With the help of Taft's estranged daughter Rosalind, dormant imaginations are brought to life. Chasing Shakespeare's lost play, Cardenio, the foursome embarks on a transatlantic journey as they pursue love, purpose, and the truth about the man from Stratford.