Issac Reed is in love with the beautiful Brenna McConnell. But Brenna's troubled past haunts her and she is afraid to become involved in a relationship with the handsome and intriguing, Issac Reed. Mrs. Edie O'Malley, the elderly widow who lives across the hall from Issac, is sympathetic to his plight and persuades him not to give up on the elusive, yet spirited young woman. Following her advice, Issac becomes determined to show the woman he loves that she has more to offer than she realizes and decides to play a game with her. Only, Brenna doesn't understand the game and refuses to play. But Mrs. O'Malley knows how to play the game so she decides to enlist the help of Jackson Bradley and Matthew Broussad to spice it up a bit. And everything was going according to plan, until Matthew decided to "improvise."