Engaging Peter is the story of Peter, a struggling documentary filmmaker who has resorted to shooting weddings for rent money. While shooting an engagement party, he attempts to make a connection with Jen, the beautiful sister of the bride. Getting nowhere, Jen`s mysterious Grandma intercedes and casts a spell. Peter becomes trapped in a repeating circle of time, getting the chance to strike up conversations with Jen fresh each time. But Peter is reclusive and awkward when he doesn`t have his camera in between himself and his subjects. Peter must relive this brief moment at the party until he gets it right and wins Jen`s heart.