Naomi is a kid who just doesn't fit in. That leads to a disappointing social life. She is smart, but she feels very lonely, and when her father has a heart attack, she decides she will become a heart surgeon. Her father is an orphan and an Jewish immigrant, and her mother is a Catholic. Her mother also struggles with depression. Naomi feels there is no one with whom she can talk, but then she makes a friend.
Teddy is the neighbor boy. He and she realize almost at once that in addition to their endearing friendship, they are also in love. Although they are children, the know with certainty that they are in it for the long haul. But, one day, Teddy moves, and Naomi realizes that suddenly, she really is alone. She reaches out to her mother, but she has a hard time pushing through her mother's mental health issues. Eventually, it is time for her to move out, though, and she goes to Wellesley College.
There, she becomes involved with the theater, and she joins the Shakespeare Society. She meets new friends through that club, and she meets Jun Oko, a Japanese girl with very wealthy parents. Eventually, she realizes that the same issues that face her also face her new friends, and she tries and fails three times to save a friend from their fate. Eventually, she decides that friends cannot always save the day.