It's 1959 and thirteen year-old Jake Young is excited. He and his buddies are looking forward to an action-packed summer before starting high school together. Unfortunately, their plans to remain best friends "forever" are shattered when Jake and his family move to Nashville. A forlorn Jake is now determined to make new friends by playing on the freshman football team at his new school. And adding insult to injury, he is subjected to humiliation by a varsity jock by the name of Donnie Ray Miles. That first year of high school is a time of gradual transition from boy to young man for Jake. As he changes physically, his attitude toward girls changes dramatically. He becomes obsessed in his pursuit of that elusive first kiss. That search is hampered by his naivete as he engages in a series of misadventures with members of the fairer sex. There's Jessie who excels in swimming and diving; there's well-endowed Portia with her elusive charms; there's Christie and her dirty tricks; and, then, there's Rachel who is only too eager to have a good time with Jake. After this series of disasters, Jake becomes enamored with a girl down the street - Katie Sawyer. She's the first true love of his life. But can that first love last?
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