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.