After recovering from the seemingly unbearable fact that his fourth-grade pen pal is a girl, Joe Cashman is surprised to find a true friend in Caitlin. They embark upon years of faithful correspondence, at first writing only of everyday details of school and play but eventually sharing their fears and anxieties of adolescence. Finding in each other the friend and confidant they so lack in their lives at home, they grow ever closer. For reasons known only to himself, Joe ends the relationship in their sixteenth summer, breaking young Caitlin's heart.
Years later Joe, now a well-known writer with a beautiful girlfriend and an exciting job, finally, unexpectedly, meets Caitlin through a mutual friend. Their resumed friendship, already awkward, is further strained by their involvement in a sexy tabloid scandal centering around Joe's famous supermodel girlfriend, Kelly, and her even more famous ex-lover, Ted, a pro baseball superstar.
Caitlin eventually discovers the reason Joe stopped writing, and the subsequent aftermath of their stormy relationship affects the lives of all those around them. Caitlin finds herself questioning her personal identity and lifestyle, Joe sets out on a quest to find stability and commitment with himself, and they both reach conclusions at once enlightening and painful.
