Buddy Smithson is a jazz loving, romantically naïve college student who has never had a serious relationship with a girl. When his best friend impulsively joins the Navy, Buddy reluctantly agrees to take care of his car and his fiancé while he is away. A few days later, Buddy meets Lexie, the vocalist with the college jazz band, and soon falls in love for the first time. Now, he must divide his time between two beautiful young women who are not aware of each other: Lexie, talented and serious, with whom he wants to spend his time, and Natalie, a popular but immature high school senior who resents the absence of her fiancé at this important time in her life. In awe of Lexie's talent and gentle disposition, Buddy is elated when she expresses her love for him, but his inexperience in matters related to romance cause him to delay explaining his commitment to Natalie, a decision he will come to regret. Natalie becomes increasingly demanding and forces Buddy into awkward situations with her friends: a red headed vamp with designs on Buddy and a and a teenage bully who Buddy must constantly outwit. Natalie writes to her fiancé almost daily, detailing her experiences with Buddy from her point of view, which is not always completely factual. Because of the letters, Buddy's friend becomes suspicious of his relationship with Natalie and their life-long friendship becomes strained. In spite of his best efforts and good intentions, Buddy's life has taken a sudden turn for the worst, from serene to chaotic. He fears his indecision may cost him the love of his life, he blames Natalie for mistakes he has made, and he needs to reassure his friend that he has done his best to keep his promise. A chance encounter with a favorite college professor prompts Buddy to gamble his future on the validity of an old adage. Will a picture save the day for Buddy?